It comes down to a question most of us avoid asking ourselves honestly:

What are you waiting for?

It’s human nature to procrastinate or put things off, however, “tomorrow” has a funny way of never quite arriving. There is always a reason to push something off. Work gets busy. Money could be better. Timing isn’t ideal. The kids are too young, or too old, or in school, or about to leave. There is always a version of life that feels like it would make travel easier, cleaner, more justified.

But that version almost never shows up.

Instead, what happens is that time moves on without us. Quietly, steadily, without asking permission. And the trip you meant to take “someday” just keeps slipping further and further from your grasp.

There is, of course, something to be said for patience. For planning. For waiting until the time is right. But travel, especially the kind that stretches you a bit, is not just a financial decision. It is also a physical and mental one.

Long flights, unfamiliar places, moving through cities, adapting to “the different”…these things are easier when you have the energy for them. That doesn’t disappear overnight, but it does change over time. The version of the trip you can take today is not necessarily the same one you will take ten or twenty years from now.

And that matters.

One of the more interesting things I’ve seen on social media lately involved a family with two young kids, both under ten. Instead of waiting for the “right time,” they sold their house, sold their car, bought a sailboat, and set off to see the world.

On paper, it sounds chaotic. Risky. Completely impractical.

In reality, they made a decision about what they valued. They chose experience over stability, education through exposure over structure, and time together creating memories as a family over the idea that there would be a better moment later.

That’s not a choice everyone needs to make. But it does highlight something important: there is always a reason not to go.

And yet, when you actually do go, the experience is almost never as intimidating as you imagined.

We tend to build up the unknown into something larger than it is. The “what ifs” stack up quickly. What if something goes wrong? What if it’s not safe? What if I don’t know what I’m doing?

But in practice, the world is a lot more balanced than that.

Yes, things can go wrong. But just as often, if not more often, things go right in ways you couldn’t have planned.

A stranger gives you directions. Someone helps you when you’re stuck. A small moment turns into something memorable because you were there to experience it.

The risk is real. But so is the upside.

This idea played out for me recently in a much smaller way.

I had a few weeks in between trips, and found myself looking at flights to the Caribbean. It’s not typically my go-to region. I don’t like beaches or resorts. I loathe heat and humidity. People often say there’s “nothing to do” on “those” islands. But I realized there was an opportunity to visit as many islands, territories, and overseas “states” as I could reasonably fit into a single trip…and avgeek out in the best way and fly a bunch of new plane types.

The airfare was reasonable. I had the time. I could plan it without too much friction.

So I went.

And it turned into one of those trips that quietly reminds you why you do this in the first place. Not because it was perfect. Not because it checked every box. But because it existed. Because it happened. Because I didn’t wait for a better version of the same opportunity that may or may not have come later.

There is also a practical side to all of this that people don’t always like to talk about.

Money doesn’t sit still. It loses value over time. Points and miles get devalued. Award charts change. Hotels get more expensive. The idea that things will simply become more affordable later is, more often than not, wishful thinking. And then there’s the other uncomfortable truth: none of us are getting any younger. We can do more, and for longer, than ever before, but our bodies will eventually start to set limits. I’m a big believer in using every bit of runway we’re given, but that also means recognizing those limits and making the most of our present abilities while we can.

Waiting can cost you more than going.

Which brings us back to the original question.

What are you waiting for?

If the answer is something real, something specific, something that genuinely needs to happen first, that’s one thing. But if the answer is vague…more time, more money, better timing, fewer unknowns…then it might be worth asking whether you’re waiting for something that doesn’t actually exist.

Because the truth is, most trips don’t happen because everything lines up perfectly.

They happen because you decide to go anyway.

The Bottom Line

There will always be a reason to wait.

There will always be a version of the future that looks slightly better, slightly easier, slightly more convenient.

But travel doesn’t reward perfect timing.

It rewards action.

Over to You

What’s the trip you’ve been putting off? And if you’re honest with yourself…why?

For me, travel is one of the clearest places it shows up.

We tend to overthink our trips before they even begin. The itinerary becomes something to optimize rather than something to experience. More cities, more countries, more “must-sees,” all packed into a fixed amount of time. On paper, it feels efficient. In practice, it often just means moving faster than the experience can keep up. A good itinerary leaves room. The “perfect” almost never does.

The same instinct shows up in how we get there. We wait for the ideal routing, the perfect departure time, the exact aircraft, the connection we like instead of the one we don’t. None of that is unreasonable on its own, but taken together it creates friction. There is almost always something slightly off. The perfect flight rarely exists. A good one gets you where you need to go at a price you can stomach, which is the whole point.

Accommodation follows the same pattern. Every hotel is a tradeoff between price, location, and comfort. You can optimize for one, maybe two, but rarely all three. And yet it’s easy to spend hours trying to find the option that somehow does. Eventually you book something that’s good enough, and once you arrive, it usually is. Not perfect, but entirely sufficient and pleasant for what you actually need it to do.

All of this builds toward a bigger realization: the “perfect trip” itself is mostly a myth. You can plan structure: where you go, how you get there, where you stay, but you cannot plan the parts that actually make a trip memorable. Those tend to be the unplanned moments: a conversation with a local, a detour where you got lost, something that happens because the plan wasn’t airtight. The same way life at home isn’t defined by perfectly executed days, travel isn’t either.

That’s why the idea of not letting perfect get in the way matters more than it seems. Waiting for ideal conditions like more time, better timing, a cleaner plan, often just delays the experience or might even prevent it from happening altogether. A good trip taken now is almost always better than a perfect trip that never happens. And once you’re on the road, holding too tightly to perfection can make the experience more rigid than it needs to be.

None of this means planning doesn’t matter. It does. But there’s a difference between planning to enable a trip and planning to control it. The former gets you moving. The latter often keeps you stuck.

The Bottom Line

There is no perfect itinerary, no perfect flight, no perfect hotel, and no perfectly executed trip. There is only the one you take. And more often than not, it’s the imperfections…the small deviations from the plan…that end up defining it.

Over to You

What’s a trip you almost didn’t take because it wasn’t “perfect”? And aren’t you glad you went anyway? What made it memorable?

It sounds like a simple question, but I’ve spent a few hours thinking about it over the last week and I really can’t come up with a succinct summary.

I went back to Ireland last week for my second trip, but it was my first trip in about fifteen years. Last time I was there I visited Dublin and Belfast. Two cities, two very different identities, two very different experiences… and technically, depending on how you count, two separate countries. At the time, I was all about going to every country, and I felt I’d seen “enough” of Ireland to count it. This trip made it clear how while it made sense at the time, I still had unfinished business.

This trip, after going to Italy and Spain, I headed to Ireland where I started in the west, spending a few days in Galway and Cork. On paper, these pretty common stops for visitors to Ireland, the kind of places people associate with “real Ireland” at least from a city perspective. And in many ways, they delivered. Lively streets, people music spilling out of pubs, that unmistakable Irish energy.

What surprised me, though, was something that in retrospect should have been expected, but I hadn’t given it any thought

The crowds.

Not just crowds, but severely intoxicated crowds. Weekend energy dialed up to a level that felt closer to a major festival than a cultural experience. And layered on top of that, a heavy presence of American tourists. Familiar accents, familiar patterns, a version of Ireland that felt almost like St. Patrick’s Day on steroids, almost exported, almost a caricature of the place.

Then I went north.

When I got to Derry, it felt different immediately. Still busy, still alive, still social… but the composition of the people I encountered had changed. There were visitors, certainly, but no Americans. More local movement, more regional travel, a different rhythm entirely. Sadly, also, this is where the intoxicated crowds in Galway and Cork gave way to socioeconomic realities…twice I witnessed medical emergencies as a result of drug/alcohol overdoses. That’s not to say that’s what Derry “is,” but it was the Derry I experienced…and at the core of it, that’s what this post is about: depending when you go, where you go within a city/country, you can have vastly different experiences.

Places like this force you to slow down, even if you don’t intend to. They ask different questions. They tell different stories depending on the parameters of your visit. And they make it very obvious that what you experience in one city…or even two…is only a fragment of country.

I finished the trip in Dublin.

And Dublin, in its own way, brought everything full circle and provided the common link between my two trips to Ireland. Not because it was representative of the entire country, but because it showed yet another version of it.

Crowds again, but this time truly global. Americans, Europeans, travelers from everywhere. A capital city energy that felt both local and international at the same time. Familiar, but still distinct from everything that came before.

So, after this long ramble, what do I think it means to “see” a country?

Because I’ve now spent time in multiple parts of Ireland, across different trips, in different contexts. And I still wouldn’t claim to fully understand it.

This is the illusion of travel at scale.

You can visit 193 countries and still only scratch the surface of each one. You can hit the highlights, the capitals, the major cities…and miss everything in between that actually defines the place.

Or you can do the opposite. Travel slowly. Move overland. Spend time in smaller towns, different regions, less obvious stops. Build a more layered understanding of a single country.

Neither approach is right or wrong.

They are just different ways of engaging with the world.

And this is exactly why I’ve come back, at least in part, to travel “lists.”

Not as a finish line, not as a scoreboard, but as a prompt, because lists force you to go beyond the obvious. They push you to see France as more than Paris. Spain as more than Madrid and Barcelona.

And even within a single trip, they remind you that diversity exists within borders, not just between them.

And then there’s places like this:

The United States alone proves the point I’m trying to get at. New York is not Chicago. Chicago is not Alabama. Alabama is not Alaska. Each one could be its own story, its own lens, its own version of what that country is…and depending when you go to each…very different experiences. New York City in July is not New York City at Christmastime.

And yet, we often reduce places to a single experience.

One city. One trip. One impression.

The reality is more complicated, and far more interesting. Because “seeing” a country is not a box you check. It’s a process. One that evolves over time, across trips, across different moments in your life. You don’t finish it.

You build it.

The Balance (Yes, Again)

This brings me back to where we’ve been over the past few weeks. You don’t need to see everything. You can’t see everything.

But at the same time, if you move too quickly, you risk seeing almost nothing at all.

The balance is in how you engage.

Not just how much ground you cover, but how deeply you experience the ground you’re standing on.

Now…Over to You

When you think about a country you’ve visited…how much of it have you really seen?

And what’s a place that completely changed your perception of a country you thought you already understood?

Over the past few weeks, I’ve been writing a lot about risk. Not eliminating it, because that’s not possible, but understanding it, managing it, and deciding which risks are actually worth taking, both in life and in travel. Travel has a way of forcing those decisions on you, often in moments where you don’t have the luxury of time or perfect information. But there’s another tension that sits just beneath that conversation, one that’s less obvious but just as important: not whether to take risks, but how fast to move once you do.

Because in travel, as in life, there is always the pull to do more. Especially in our 24/7 always plugged-in and online lifestyle of 2026.

We are living in an era that rewards acceleration and “likes”. Scroll through social media and it feels like everyone is in motion, racing toward something: the youngest to visit every country, the fastest to visit every country in Europe, the most efficient itinerary imaginable. There is an unspoken assumption that if you are not maximizing your time, you are somehow wasting it. And if you are someone who is naturally curious, ambitious, or driven, it is very easy to internalize that message without even realizing it.

It’s an instinct I’ve certainly lived, and I know it’s one many of my friends experience as well. But over time, I’ve also come to recognize the tradeoff that comes with it. Because when everything becomes about the next place, the next milestone, the next achievement, you begin to lose something along the way. You stop fully experiencing where you are, because part of your mind is already somewhere else. Planning the next trip instead of enjoying the one you’re on. Looking for the next race instead of enjoying the process of training for your current one. You get the drift….

I learned this lesson long before I finished visiting every country. Before I did my first Ironman triathlon in 1996, I asked a veteran of the race what it would feel like to cross the finish line. I expected something dramatic, something transformative, the kind of moment that changes how you see everything that comes after it.

His answer was much simpler, and at the time, a bit surprising. He said you would feel incredible…for a moment. And then, almost immediately, you would start to wonder what comes next when the goal that’s consumed so much of your life for so long is finally accomplished.

It took me years to fully understand what he meant. When you invest so much time and energy chasing a goal, the achievement itself can feel fleeting. The finish line, which you imagined as an endpoint, turns out to be just another transition. And if you are not careful, you move on too quickly, without ever really sitting in what you just accomplished.

Travel can fall into that exact same pattern.

Looking at something like this, it is easy to feel a sense of scale. Nearly 3,000 flights, hundreds of airports, millions of miles traveled across the world. It represents years of movement, planning, and experience. But it also makes something else very clear, something that is easy to overlook when you are caught up in momentum.

You cannot see it all.

No matter how fast you go, no matter how efficiently you plan, no matter how many places you check off, there will always be more. Entire regions, cultures, and experiences that remain just out of reach. That realization can feel overwhelming at first, but over time, it becomes something else entirely. It becomes freeing.

Because once you accept that you won’t see everything, you can finally stop trying to.

There is a line in Billy Joel’s Vienna that captures this tension perfectly: “You can get what you want or you can just get old.” And the story behind the song adds another layer to it. Billy Joel once described visiting his father in Vienna and noticing an elderly woman, well into her later years, sweeping the street. When he asked why she was still working, his father explained that she had a job, she felt useful, she was part of something. She wasn’t finished.

That moment became the metaphor behind the song. Not everything in life is meant to be rushed toward an endpoint. There is no single moment where you are “done.” The meaning comes from the act of doing, of participating, of being engaged in the world over time.

That idea runs directly against the urgency we often bring into travel.

There is always more you could be doing. Another viewpoint to chase, another restaurant to try, another town just an hour away that everyone insists you have to see. The list is endless, and if you let it, it will define your experience.

But sometimes the right choice is the opposite. To stay where you are. To watch the light change. To let a place reveal itself slowly instead of trying to extract everything from it as quickly as possible. Those quieter moments rarely feel urgent at the time, but they are often the ones that stay with you long after the trip is over.

Places like this reinforce that idea in a different way. You can spend hours, days, even weeks in a landscape like this and still feel like you have only scratched the surface. And yet, the value is not in how much ground you cover, but in how present you are while you are there.

Because even in the most visually striking places, it is rarely just the scenery that defines the experience. It is the conversations, the unexpected moments, the subtle interactions that were never part of the plan. Those are the things that give travel its depth, and they are also the things you miss when you move too quickly.

For all the miles, all the flights, and all the places, something like this still stands out more than almost anything else. Not something acquired along the way, but something given. A reminder that behind all the movement and ambition, there are people who support you, encourage you, and make those journeys possible in the first place.

Travel, at its core, is not about accumulation. It is about connection. And the moments that carry the most weight are rarely the ones you can plan or optimize. They are the ones that happen when you slow down enough to actually experience them.

This is the balance.

There is nothing wrong with wanting to see more, to go further, to push yourself beyond what feels comfortable. That curiosity is what drives travel in the first place. But if you move too fast, you risk turning the experience into something transactional, a series of boxes checked rather than moments lived.

Because whether you have two weeks, two years, or fifty years ahead of you, the goal is not to fill that time as efficiently as possible. It is to fill it with things that bring meaning, joy, and connection. And those things do not come from rushing.

They come from being present.

Over to You

Have you ever felt this tension while traveling…the pull between doing more and actually experiencing what is right in front of you?

And when have you gotten that balance right?

For me, one of those moments came recently in Potenza, Italy. It’s a place that feels remote even by Italian standards, perched high in the mountains as the country’s highest regional capital. Getting there requires more than a little bit of time and planning. There’s currently no train service, so you take a bus from Naples or Foggia, and even then you’re not quite finished. From the bus stop, you can take a taxi (which I couldn’t find) or a small shuttle train that climbs toward the town. And once you arrive there, there are still several hundred steps and staircases to reach the old town itself. It’s not that difficult, but it’s enough to remind you that you are not in a place built for convenience or mass tourism.

The more interesting part of the story, though, was not the journey in. It was trying to escape the next morning.

I had an early start…one of those oh-dark-thirty departures that feels closer to the middle of the night than the beginning of the day. I made my way down to the shuttle train station, which, in fairness, was considerably easier going downhill than it had been the day before. The station was quiet. I checked the schedule I had photographed the previous day and waited.

And waited.

Ten minutes passed beyond the scheduled time, then fifteen. I started to worry about my connecting bus which was leaving soon. At first, it felt like a minor delay, the kind that happens everywhere. But as the minutes ticket on by mild panic started to settle in. Connections depend on timing, and timing, in this case, was not on my side .

At that point, a man approached me and asked, in Italian, what I was doing there. Now, I don’t speak Italian beyond maybe 100 words, but Potenza is one of those places where you still don’t find much English, but with my 100 words and google translate I managed to explain that I was waiting for the overdue train. I showed him the schedule on my phone.

He looked at it, confused…paused, and then pointed to a sign on the wall nearby.

The schedule I had taken a pic of and which was prominently posted on the wall was from 2024. The current one…the one that mattered…was different and posted on another wall I never saw. The train I was waiting for was not coming.

With only a few minutes left before my onward connection, the situation had moved from inconvenient to missing my bus and the next region I planned to visit. I explained as best I could that I needed to be at the bus stop quickly. There may have been some wild Italian-style gesturing…there was no hesitation in his response. He simply gave me that “come with me” gesture and started speed walking.

This is the point in the story where instinct takes over.

We are taught, quite reasonably, not to trust strangers. That instinct serves an important purpose, and ignoring it entirely would be naïve. But travel also introduces moments where rigidly applying that rule doesn’t quite fit the reality in front of you. The decision becomes less about rules and more about reading the situation: tone of voice, body language, urgency, context.

There was nothing theatrical about the moment (well, nothing more than is that “passion” that Italy does so well. No attempt to persuade, no ambiguity in intent. It was direct, practical, and immediate. It felt like help.

So I followed.

He led me to his car, parked a short distance away, and we set off. What followed was a drive that can best be described as efficient in the way that only Italian driving can be: fast, controlled, and entirely focused on the task at hand. Within minutes, we arrived at the bus stop, just as my connection was about to depart.

There was no ceremony to the end of it. A brief exchange, a quick and heartfelt grazie mille, a nod of acknowledgment, and he was gone.

The entire interaction lasted perhaps six or seven minutes. Its impact on me will last much longer. He made a difference.

“Look for the Helpers”

The phrase “look for the helpers” comes from Fred Rogers, who shared a piece of advice his mother gave him when he was a child. Whenever he saw something frightening in the news, she would tell him to look for the people who were helping. The idea was simple: even in difficult or uncertain situations, there are always individuals who step forward to make things better.

It is an idea that can feel almost overly saccharine and sentimental in the abstract. But in practice, it is something most experienced travelers recognize immediately.

Because if you have traveled enough, you have your own version of this story. The stranger who offered directions when you were lost. The driver who went out of their way to make sure you arrived safely. The person who noticed something was wrong and intervened without being asked. These moments are rarely dramatic, but they are often decisive.

At the same time, travel also teaches the opposite lesson. There are moments when trust is misplaced, when someone takes advantage of uncertainty or inexperience. Those stories exist as well, and they are part of the same reality. The challenge, then, is not to choose between trust and skepticism, but to find a balance between the two.

There is no precise formula for doing this. Experience helps. Awareness helps. Over time, you become better at interpreting the signals that surround a situation. You learn to recognize when something feels off, and just as importantly, when it doesn’t. Instinct, in this sense, is not blind; it is informed by everything you have seen and learned along the way.

The goal is not to move through the world assuming the best of everyone, nor is it to assume the worst. It is to remain open enough to accept help when it is genuinely offered, while staying aware enough to recognize when it is not.

That morning in Potenza was not extraordinary in the grand scheme of life or travel. It did not involve danger or dramatic stakes. Missing a region to visit wouldn’t be the end of the world. But it served as a reminder of something easy to overlook, particularly in this day and age when it often feels as though division and distrust dominate the narrative.

On the ground, in real places, among real people, the story is almost always more nuanced. There are risks, certainly. There are those who wish to divide us, absolutely. But there are also many people who, without hesitation, choose to help.

And if you pay attention, you will find them.

Over to You

What is your “helper” story? When has a stranger stepped in and changed the course of your trip?

And just as importantly, when have you trusted your instincts and decided not to?

These are the moments that shape how we travel and how we understand the world around us.

Hotels feel like somewhere you should feel safe and secure. You check in, drop your bags, exhale a little. But they also concentrate risk in ways most travelers don’t always think about. At the low end, maybe it’s something minor: an item that goes missing, a room that doesn’t feel quite secure. And at the far end there’s the rare, but very real risks: you have fires, natural disasters, or even targeted attacks. Hotels, especially international chains and high-traffic properties, can be visible, predictable gathering points.

As I said in the last couple of posts, and it’s worth repeating here: you can’t erase all risk. But you can understand which risks are worth taking and which ones are simply careless.

The good news is that hotel safety doesn’t require paranoia or a checklist that takes an hour to complete. It’s about small, deliberate habits that might take a minute or two, but meaningfully change your exposure. The kind of things that, once you start doing them, become second nature.

1. Location, Location, Location

The moment you arrive in your room, before you unpack or even sit down, take a minute to understand your surroundings. Most people walk straight in, drop their bags, and never look up. That’s a missed opportunity.

Start with the basics: where are the nearest emergency exits? Not the one you used to get there, but the closest alternative. If there’s a fire or blockage in the hallway, your primary route may not be available, and in those moments, familiarity matters more than speed.

Floor selection also plays a significant role, even if it’s something you decide in advance. Ground floors are more accessible to opportunistic intruders, while very high floors can complicate evacuation or emergency response. A general rule of thumb is to stay somewhere between the third and sixth floors which is high enough to reduce casual access, but still within reach for most emergency services.

Even the orientation of your room is worth considering. Rooms facing busy streets or main entrances tend to be more visible and, by extension, more exposed. Quieter sides of the building, while less exciting, often provide a bit more privacy and distance from potential threats.

None of this guarantees anything. But it subtly shifts the odds, and over time, that’s what matters.

2. Stay Safe Inside the Room

Once you’re inside your room, the next step is straightforward: use the security features that are already there. Deadbolts, chains, locking bars, these are not there to look pretty, and like seatbelts they don’t help if you don’t use them. They are simple, effective layers of protection, and it’s worth using all of them consistently.

The idea here isn’t to create an impenetrable space. It’s to introduce friction. Most unwanted situations are opportunistic rather than highly planned, and even small barriers can be enough to deter someone from trying.

There are also a few low-effort habits that can add an extra layer of security. Many travelers are familiar with the “hanger trick,” where a hanger is looped through the latch mechanism to make the door harder to open from the outside. It’s not foolproof, but it adds resistance and noise, and resistance is often enough.

The point is not perfection. It’s making your room a less appealing option than the one next door should someone be on a mission.

3. Don’t Broadcast Your Room Number

One of the most overlooked aspects of hotel safety is information…specifically, how casually it’s shared.

At check-in, a well-trained front desk should never say your room number out loud. If they do, it’s a small but telling signal that attention to detail may be lacking. You don’t know who is within earshot, and neither do they.

The same principle applies to your own behavior. It’s easy to mention your room number in passing: at the bar, in the spa, or while coordinating plans. But those small disclosures can add up, especially in environments where people are constantly moving in and out.

When you’re outside the hotel, a bit of discretion goes even further. There’s rarely a need to tell someone exactly where you’re staying, particularly if you’ve just met them. If an address is required for a practical reason, it’s far safer to write it down than to say it out loud.

You don’t need to assume the worst about everyone. But you also don’t need to make yourself easy to track.

4. Know Your Room (and What Might Already Be in It)

The first few minutes in your room set the tone for your stay, and they’re also the right time to do a quick, practical check.

Before fully entering, it’s a good habit to prop the door open with your luggage and take a brief look around. Check the bathroom, glance inside the closet, and pull back the curtains. You’re highly unlikely to find anything or anyone, but you’re confirming that everything is as it should be.

After that, turn your attention to the bed. Bed bugs are an equal-opportunity problem; they show up in budget properties and 5 star luxury hotels alike. A quick inspection of the sheets and mattress seams for small dark spots, reddish stains, or visible insects can save you from a much bigger issue later.

Luggage placement also matters more than most people realize. Setting your bag directly on the floor (especially on carpet) creates an easy path for pests to find their way in. Using a luggage rack or keeping your bag elevated is a small adjustment that significantly reduces that risk.

These steps take less than a minute. But if you skip them, you’re leaving things entirely to chance and potentially opening yourself up to months of pain down the road.

5. ICE: In Case of Emergency

Finally, there’s the question of what happens if something actually goes wrong. In those moments, clarity and speed matter, and that starts with knowing your options in advance.

Take a moment when you arrive to check a few basics. What is the local emergency number? It’s different in every country, and assuming it is going to be 911 or another common option can waste valuable time. Does the room phone work? It’s easy to ignore, but it provides a reliable backup if your mobile phone is out of battery, has no signal, or isn’t connected to a local network.

It’s also worth noting the location of fire alarms, extinguishers, and any emergency call points on your floor. These details are often posted, but rarely noticed until they’re needed. Most hotels will have a diagram of the emergency escape route on the back of the door…take a quick glance before you need it.

Your smartphone is an incredible tool…until it isn’t. Having a simple, low-tech backup plan is part of traveling responsibly.

The Bottom Line

Taken together, this might seem like a lot of small and paranoid precautions. In reality, it’s a couple of minutes max of awareness at the start of your stay.

You’re not trying to predict every possible scenario. You’re simply reducing your exposure to the most common and most avoidable risks. That distinction matters.

Because the goal, as always, isn’t to eliminate risk entirely. It’s to make sure that the risks you do take are the ones that lead to meaningful experiences, not preventable problems.

Over to You

What are your go-to hotel safety habits? Anything you’ve learned the hard way that others should know?

Drop them below, because the best travel advice is almost always written in hindsight.

So let’s make this practical.

Here are five things you can do right now to meaningfully reduce your travel risk, without turning your trip into a hyper-controlled, joyless operation.

1. Don’t Put All Your Money in One Place

If your wallet or purse disappears…whether you lost it or someone helped it disappear…you don’t want your entire trip disappearing with it.

The fix is simple, and it’s amazing how many people don’t do it: split your resources. Carry your primary wallet as usual, but keep a backup credit card and some emergency cash somewhere separate. That might be your luggage, your hotel safe, or even a different bag.

This isn’t about paranoia, it’s about basic resilience. I’ve seen travelers go from completely stuck to completely fine just because they had a backup card tucked away. Same problem, totally different outcome. One person is canceling their trip. The other is ordering an umbrella drink and figuring out next steps.

Don’t let a single point of failure end your trip. I admit I’ve failed to follow my own advice here multiple times thinking “it won’t happen to me” but travel enough and it eventually will.

2. Back Up What Actually Matters (Not Your Whole Life)

Travel comes with friction. It’s as inevitable as the sun rising and setting each day. Bags get delayed. Things get misplaced. Occasionally, stuff just vanishes into the void.

So the question isn’t “how do I prevent that entirely?”…you won’t. The question is: what can I absolutely not function without?

For most people, that list is pretty short:

• Prescription medication

• Glasses, contact lenses, or other assistive devices

• Essential documents such as your passport

Those are the things worth duplicating or planning around.

What’s not on that list? Your third backup phone. Your second laptop. Your “just in case” tablet. I know people who travel like they’re opening a Best Buy pop-up, and it’s completely unnecessary. If your laptop dies, you log into the cloud on a new one. If your phone breaks, you replace it.

Be thoughtful about redundancy where it matters, but don’t confuse preparation with overpacking. Pro-tip for your passport and other critical docs: always store a PDF copy in the cloud…that way, if it decides to wander off you at least have something to show the police or other officials in the meantime.

3. Tell Someone Where You Are (But Don’t Tell the Internet)

There’s a sweet spot between being completely off-grid and broadcasting your every move to the world.

When you’re doing something even slightly higher risk…remote hiking, long solo drives, unfamiliar areas at night…tell someone you trust where you’re going and when you expect to be back. Build in a little buffer so they don’t panic if things run late, but make sure someone has a general sense of your plan.

At the same time, resist the urge to post everything in real time, especially in places where security is less predictable. Not everyone following you has good intentions, and you don’t need to make it easy for anyone to track your movements.

Share the story later. Experience it fully in the moment. A little bit of discretion goes a long way.

4. Safety in Numbers…But Not a Traveling Circus

There’s truth to the idea that two heads are better than one. Traveling with a companion can make decision-making sharper, provide a second set of eyes, and generally reduce risk.

But there’s a tipping point.

As groups get larger, they become more visible, less flexible, and frankly more chaotic. You’re more likely to stand out, more likely to attract attention, and almost guaranteed to have at least one person making questionable decisions that affect everyone else.

Large groups can also become easier targets. They’re predictable, they move slower, and they often signal “tourist” from a mile away.

Smaller groups, or even pairs, tend to move more intentionally. They blend in better, adapt faster, and keep a tighter awareness of their surroundings.

Travel like a team, not an entire traveling circus.

5. Go Where the Locals Go (With Eyes Open)

There’s a reason certain places show up in every guidebook. They’re famous, accessible, and designed to handle large volumes of visitors.

They’re also predictable.

And anything predictable (big chain hotels, major tourist restaurants, packed festivals, iconic attractions) can become a natural focal point not just for travelers, but for people looking to take advantage of them.

That doesn’t mean you should avoid these places entirely. Some are absolutely worth seeing. But it does mean you should approach them with awareness.

Balance them out by spending time where locals actually live their lives. Stay in neighborhoods that aren’t built exclusively for visitors. Eat at places that aren’t optimized for tourists. Explore beyond the obvious.

You’ll often find that not only do you feel more grounded and less targeted, you also have a far richer experience.

One small reality check: your immune system is not local. That incredible street food spot might be perfectly normal for residents and a full-blown adventure for you. Ease into it. Your stomach will thank you.

The Bottom Line

Derisking your travel isn’t about wrapping yourself in bubble wrap or eliminating every unknown.

It’s about making a series of small, smart decisions that compound in your favor. So when something inevitably goes wrong, it’s not catastrophic…it’s just an inconvenience.

You’re still moving. Still exploring. Still saying yes.

And that’s the whole point.

You can stay home, sit on the couch, watch TV, avoid difficult places, avoid difficult people, avoid uncertainty, and build a routine where almost nothing truly unexpected ever happens. You can convince yourself that this is wisdom. After all, if you never go anywhere, never try anything, and never expose yourself to unfamiliar situations, the odds of something going sideways drop dramatically. Unless, of course, the house burns down. Or your health fails. Or life finds some other way to remind you that total safety is mostly an illusion.

That is the problem with a fully “derisked” life. It may feel safer in the short term, but it is definitely not more rewarding. And at some point, whether we admit it or not, most of us are not really asking how to avoid all risk. We are asking a deeper question: what makes life worth living in the first place?

There is a quote often associated with Thoreau that hits me hard:

"I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived"

That, to me, gets to the core of travel and of risk. The goal is not to eliminate uncertainty from your life. The goal is to avoid waking up one day realizing that you spent decades trying so hard to protect yourself from the essence of life that you forgot to actually live it.

Of course, there is another extreme. Some people do not merely tolerate risk. They actively seek it seemingly 24/7. They bungee jump off bridges, throw themselves into violent rapids, and treat fear as if it were a hobby. I am not wired quite that way, even if I have occasionally found myself brushing right up against that world.

That is where this gets interesting, because there are risks, and then there are reckless decisions. Those are not the same thing, even if they can look similar from the outside. Recklessness is blind. It ignores context, dismisses consequences, and often has very little payoff beyond the adrenaline hit or the story afterward. Risk, by contrast, can be informed. It can be measured. It can be chosen with your eyes open. One is chaos for chaos’s sake. The other is an intentional bet that the reward outweighs the downside.

That distinction matters enormously in travel.

People who work in the area of risk management view risk analysis as a matrix: on one axis, risk. On the other, reward. Low risk and low reward is the easy default. Staying home. Doing what you have always done. Nothing wrong with it in moderation, but no one is writing epic memoirs about the week they stayed in and reorganized the pantry. High risk and low reward is where recklessness lives. That is where bad judgment disguises itself as bravery. There is very little romance in making dumb choices with terrible upside.

Then you get to the more interesting quadrants. Low risk and high reward is where many of us should be living more often than we do. Take the trip. Book the ticket. Speak to the stranger. Wander the neighborhood. Try the thing that scares you just a little. Most of the time, these are not reckless moves. They just feel scary because comfort is addictive. And then there is high risk and high reward, which can absolutely be worth it, but only when you are honest with yourself about the tradeoffs and your own appetite for uncertainty.

The sweet spot is personal. But if I had to guess, for most people it is probably further out than they think.

That is where travel becomes such a useful teacher. Travel exposes how many of our “safe” decisions are really just habits. It shows us that what we often call prudence is sometimes just fear wearing sensible shoes. It also forces us to sort out what we really mean by risk. Is the danger physical? Emotional? Financial? Logistical? Social? Is the reward fleeting, or does it change you in some lasting way?

Take something like sledging in New Zealand, for example. If you have never heard of it, imagine whitewater rafting, except instead of being inside the raft, you are in the river itself clinging to a board and attempting to look like this was all a very reasonable life choice. It sounds absurd because it is. But it is also structured, guided, and managed. It is not random chaos. It is informed risk wrapped in a ridiculous package.

And because of that, it becomes the kind of experience that stays with you. Not just because it was intense, but because you chose to do something that demanded presence. The river did not care about your to-do list, your inbox, your insecurities, or your plans for next week. It forced you fully into the moment. That kind of reward is hard to get from safe, padded, predictable living.

Lately, these thoughts have collided with something much more real and much less theoretical: having a seriously ill parent. This is not the main point of the piece, but it is part of how I have been thinking about informed risk lately. There are times in life when the question is not just whether something sounds exciting or meaningful, but whether it is responsible given the circumstances around you.

That was part of the reason Yemen no longer made sense for me recently. It is not that Yemen is not worth seeing. It absolutely is. But it is also not a place where you can just hop on the next hourly flight home if something goes wrong. If someone passes away while you are somewhere like that, there is a real chance you simply do not make it back in time. That is not drama. That is logistics.

That, to me, is where informed risk-taking becomes less abstract and more personal. It is not about becoming timid. It is about recognizing that context matters. This is also one reason I have spent more time in Europe lately. Worst case, if something happens at home, I can generally be back in the United States from Europe in under 24 hours. As it happens, that exact logic mattered this week. And I did make it back in time. That does not mean Europe is “safe” and Yemen is “bad.” It means that in one season of life, one risk/reward calculation made sense and another did not.

That is what maturity in travel looks like. Not staying home forever. Not pretending all destinations carry the same consequences. Just knowing your own matrix.

The funny thing is that most of us do not need encouragement to be more cautious. The world gives us that constantly. Family gives us that. News gives us that. Algorithms especially give us that. We are endlessly reminded of what can go wrong, what might happen, what could fall apart. Very few voices are out there saying, yes, but what might happen if you go anyway? What if the upside is bigger than your fear? What if the thing that feels risky is actually the thing that makes your life more vivid, more textured, more worth remembering?

I suspect that for most people, the real growth is not in becoming more reckless. It is in becoming more honest. Honest about what actually matters. Honest about what is merely comfortable. Honest about the fact that many of the best experiences in life begin with some version of I am not totally sure about this.

That does not mean everyone needs to jump off bridges, raft through rapids, or throw themselves into whatever adrenaline circus is nearest. It means knowing your personal sweet spot and admitting that, for most of us, it probably involves taking more risks and trying more things than we currently do.

Because there is a huge difference between derisking your life and shrinking it.

Travel is one of the clearest ways I know to test that idea. Not because every trip has to be extreme, but because every trip asks some version of the same question: are you here to protect your routine, or are you here to expand your life? Sometimes the answer is rest. Sometimes the answer is caution. Sometimes the answer is staying closer to home because that is what your life demands in that moment. But sometimes, maybe more often than we admit, the answer is to go. To try. To say yes. To accept that life cannot be fully optimized against pain without also being optimized against joy.

So I will leave you with this:

When did you take a risk and it really paid off?
And when did you realize you had gone just a little too far?

Because most of us do not need a push toward recklessness.

We need permission to live a little more fully.

That is Valencia for me right now.

I booked this trip without realizing I’d be landing in the middle of Las Fallas, the city’s most famous festival and one of the wildest cultural events in Spain. Fortunately, prices were still reasonable, logistics held together, and instead of getting punished for my lack of planning, I somehow got rewarded for it. I walked into a city that had effectively turned itself into an open-air fantasy world of giant sculptures, street celebrations, firecrackers, music, and collective sleep deprivation.

And honestly, it slaps.

If you have never been, the simplest explanation is that Las Fallas is a festival built around art, satire, neighborhood pride, noise, and fire. Throughout the year, different neighborhoods commission and construct enormous sculptural installations called fallas. These are not casual decorations. They are elaborate, expensive, technically impressive works of art, often playful or surreal, sometimes political, sometimes absurd, and always designed to be noticed. During the festival, they are displayed throughout the city, admired by locals and visitors alike, and then, at the end, all of them (except one which is “pardoned”) are burned. That is part of the tradition. The beauty is temporary on purpose so it can happen again next year.

The city lives differently while Fallas is happening. During the day, you wander from one installation to another, turning street corners and suddenly finding yourself face to face with some giant, hyper-detailed creation that looks like it came from a fever dream. At night, the energy shifts. The crowds get thicker, the lights get brighter, and the whole place feels like it is operating on pure adrenaline and communal momentum. Valencia stops being just a city and starts behaving like a living event.

What struck me almost immediately was that the festival itself is not just about spectacle. It is also about participation. The city is outside. People are moving, talking, laughing, drinking, lingering, and sharing the experience. That matters, especially when you are traveling alone.

Because here is the truth about solo travel: your experience is mostly on you.

Yes, some places are more open than others. Yes, some people are warmer than others. Yes, luck matters. But if you are alone in a city and want more than photos and observations, at some point you have to participate. You have to put yourself out there, speak to someone, ask a question, accept a little awkwardness, and see what happens. Travel is not just about where you go. It is also about whether you are willing to step toward other people once you get there.

That thought hit harder yesterday because I had one of those conversations that lingers, though not for the best reason. I met someone working at a restaurant, an immigrant from Asia who has lived in Spain for more than twenty-five years. Their partner is from another European country, so the two of them have also built their lives here from the outside. And for what felt like a very long time, all I heard from them was how unwelcoming the Spanish are, how impossible it has been to connect, and how even after all these years they still do not feel accepted in Valencia.

Now, to be clear, I am not saying their experience is invalid. It is their experience, and I am sure it is real to them. But there is a difference between acknowledging that connection can be difficult and deciding that connection is impossible. The whole conversation felt so relentlessly negative that I eventually found myself looking for an exit. People who have settled too comfortably into resentment can drain the oxygen out of a room.

And the thing is, my own experience here has been almost the exact opposite.

Not because I am somehow magical. Not because every Valencian I meet is trying to become my best friend. But because I speak at least some Spanish, I make an effort, I ask questions, I smile first, and I am willing to accept that not every interaction needs to become some deep, life-changing bond to still be worthwhile. Especially during a festival like Fallas, when half the city seems to be operating with a little extra courage courtesy of whatever is in their cup, it is not that hard to meet people if you are open to it.

That is the philosophy piece here, and honestly it applies far beyond Valencia.

A lot of travelers say they want “authentic connection,” but what they really want is for connection to arrive effortlessly, on their terms, without discomfort, rejection, effort, language barriers, or vulnerability. That is not how it works. Not in Spain. Not anywhere. Real human connection, even the casual kind, requires initiative. You do not need to leave a place with lifelong friends. You do not need a dramatic story about how you were adopted into a local family and now return every Christmas. Sometimes the win is much smaller, and still meaningful: a shared laugh, a recommendation, a drink, a conversation that lasts twenty minutes longer than expected, a sense that for one evening you were not just observing the city, but participating in it.

Fallas is actually a perfect setting for this lesson because the festival itself is communal. These sculptures are not just dropped in by some anonymous event company. They come from neighborhood organizations, local traditions, local pride, local energy. You can admire them as an outsider, sure. But the experience gets richer the moment you remember that these are not props for your content. They are part of a city’s identity, created by people who live here, celebrate here, and understand layers of meaning you probably do not.

That is one reason I love being surprised by events like this. They break the tidy version of travel. You think you are arriving in one kind of place and instead you land in something louder, stranger, and much more alive. They also force you to decide what kind of traveler you want to be. You can stay detached and consume the event visually, moving from sculpture to sculpture like you are scanning museum exhibits. Or you can lean in, ask questions, talk to people, and let the city become social rather than scenic.

And then there is the deeper travel lesson underneath all of this. So much of travel is not about whether a place is welcoming in some abstract, universal sense. It is about whether you are willing to give the place something to work with. That does not mean ignoring real barriers. Some communities are more closed. Some societies are harder to crack. Some conversations go nowhere. Some people simply do not want to talk, and that is fine. But if you bring curiosity, humility, and a little linguistic effort, you are dramatically increasing your odds.

That matters because negativity can become self-fulfilling. If you walk into a place already convinced that nobody wants you there, you will notice every cool interaction as an exception and every cold interaction as proof. But if you arrive open, observant, and willing to engage, you start giving reality a chance to surprise you. Not perfectly. Not every time. But often enough that a city begins to feel less like a backdrop and more like a relationship.

That is what I keep thinking about as I walk through Valencia this week. The sculptures are amazing. The festival is ridiculous in the best possible way. The whole city feels enhanced. But the real story is not just the art in the streets. It is the chance to step into the mood of a place and decide whether you are going to remain separate from it or become, even briefly, part of it.

Traveling alone does not mean being alone the whole time. It means that connection is less likely to happen by accident and more likely to happen because you chose it. That is not a burden. It is a gift. It means your trip is not just something that happens to you. It is something you actively shape.

And that is probably the bigger lesson here.

Valencia gave me Fallas by accident. What I do with that accident is up to me.

So I will leave you with this: what is a time you put yourself out there while traveling, connected with someone, and your trip was richer because of it?

Because places matter, of course.

But more often than not, it is the people who make them unforgettable.

That is absolutely not how travel works.

In fact, the longer you travel, the more mistakes you are likely to make. Not because you are careless, but because you are constantly operating in unfamiliar systems: different languages, different transportation networks, different bureaucracies, different cultural expectations. Travel necessarily is friction, and friction inevitably produces mistakes. The real skill of travel is not avoiding mistakes entirely…that’s impossible. The real skill is learning from them, admitting them, and sharing those lessons so others can benefit.

Which brings me to something I did yesterday.

I lost my passport.

A Train Odyssey

Yesterday was one of those classic European travel days where the phrase “you can’t get there from here” becomes painfully real. The itinerary involved four trains and three connections, the sort of day where every transfer made feels like a small victory and every minor delay feels like it might unravel the entire plan.

By the time I arrived at my hotel, I was exhausted but also quietly proud of myself. Not because of the train journey itself, but because the entire check-in conversation was happening in French. The receptionist and I were chatting comfortably, making little jokes, and the interaction felt natural.

Usually when French hotel staff see a passport from an English-speaking country they immediately switch to English. Contrary to the stereotype, it’s not because French people are rude. Quite the opposite. They generally believe they’re helping make life easier for their guest.

But this time we stayed in French, and I was enjoying the small victory.

Then she asked for my passport for the registration.

That’s when I realized I didn’t have it.

The Moment You Know It’s Gone

My first thought was that it had simply slipped somewhere in my bag. That happens all the time when you’re moving quickly through trains and stations. So I started digging through everything: the main compartment, the zippered pockets, the side compartments that you forget exist until moments like this.

Nothing.

Fortunately I travel with multiple passports, so I handed over the other one and didn’t say anything. The check-in process continued normally, and I went upstairs to my room.

Once inside, I yeeted the entire contents of my bag onto the bed.

Still nothing.

At that point I was about ninety-nine percent sure the passport was gone.

Here’s the embarrassing part: I wasn’t actually worried about replacing it. Passports can be replaced. It would have been annoying, but manageable. And since I had another passport with me, I wouldn’t have needed an emergency embassy visit or a forced immediate return home.

What bothered me was something far nerdier.

The stamps.

That passport contained years of travel history, and the idea of losing that record felt worse than losing the document itself.

A Lifetime in Passports

Over time, passports quietly become a kind of personal archive. They record where you’ve been, the eras of your life, and the phases of your travel.

The longer you travel, the more these small booklets accumulate. Each one represents a chapter of movement through the world and thousands of stories and memories.

And of course the real memories live inside the pages: immigration stamps, visas, and handwritten notes from border officers who were sometimes amused, sometimes suspicious, and occasionally just bored.

When you travel long enough, these passports stop feeling like documents and start feeling like a very real part of you…and that’s something no amount of time or money can really replace.

The Recovery Attempt

On the off chance that the passport might turn up, I started working through possibilities. First step: submit a lost-and-found request through the French SNCF train company lost and found system. Maybe someone would find it on a train seat and turn it in.

The next easy possibility to explore was the hotel I had just left.

I honestly thought this was unlikely. I had only taken the passport out briefly when checking in the previous day, and I had seen the receptionist multiple times afterward. Surely if I had forgotten it there he would have handed it back.

Still, it was worth checking.

So I called.

“Yes,” he said.
“I have it. That is why I have been calling you.”

This was interesting, because my phone showed exactly zero missed calls.

But the important part was this: he had the passport.

Apparently he had forgotten every single time he saw me after check-in to give it back.

He offered to mail it to me. Given the demonstrated forgetfulness on his part involved so far, I decided it would probably be wiser to go back and pick it up in person.

Not the worst outcome in the world. Lose a day of seeing things I’d hoped to see, but recover countless memories.

The Lesson

The story itself is amusing in hindsight, but the important part is the lesson that follows. Travel mistakes only become valuable if you actually learn something from them.

When I checked out of my hotel this morning, I did a full inventory check before walking out the door: passport, wallet, spare cash. I have always done a quick sweep of hotel rooms before leaving…checking outlets, drawers, and bathroom counters…but from now on I’m adding something else.

Before leaving any hotel, I will physically confirm that I have my passports and wallet.

It takes five seconds and can prevent a very complicated day.

Another Classic Travel Mistake

Of course, losing documents isn’t the only travel mistake people make. Another extremely common one involves booking errors.

Almost every traveler has done it at least once: booking the correct flight or hotel, but for the wrong date. When you are juggling multiple reservations across time zones, currencies, and itineraries, it’s surprisingly easy to click the wrong day.

I solved this problem with a simple habit. Every time I book a flight or hotel, I forward the confirmation email into two apps: TripIt and Flighty Both apps automatically build your itinerary.

The key is reviewing that itinerary immediately after booking. Several times I have caught mistakes right away: wrong dates, wrong connections, or overlapping bookings. In many cases these errors can be fixed for free if you catch them quickly. Fixing them on the day of travel is almost always far more expensive.

Traveling Better

The goal of travel isn’t perfection. The goal is improvement.

Every mistake teaches you something. Lose a passport and you build better routines. Book the wrong date and you develop better systems. Miss a train connection and you learn how transportation networks actually work.

If you refuse to admit your mistakes, you guarantee you will repeat them. But if you share them honestly, you help yourself—and other travelers—move through the world a little more wisely.

Your Turn

So I’ll ask the same question I asked several travel friends last night when I told them this story.

What’s a travel mistake you made?

And more importantly: what did you learn from it, and how do you make sure others benefit from that lesson?

Because no matter how experienced you are…

Travel will humble you eventually.

And honestly, that’s part of why it’s so valuable.

Hurghada.
Sharm el Sheikh.
Cancun.
Large parts of the Caribbean.
Papeete.

They’re labeled too packaged, too resort-heavy, too manufactured for inexperienced and lazy travelers. Places where the experience is curated, buffered, fake. And yes, that version absolutely exists. You can fly thousands of miles, check into a gated compound, rotate between buffet lines and infinity pools, and leave having seen little more than a swim-up bar and the inside of an airport transfer van.

And there is nothing inherently wrong with that. Rest has value. Escapism has value. Sometimes umbrella drinks and sunburned afternoons are exactly what that era of your life calls for.

But here’s the part that rarely gets discussed: these places are not inherently shallow. They are simply amplifiers of your intent.

They are what you make them.

Sharm el Sheikh: Beyond the Resort Perimeter

Most visitors to Sharm el Sheikh never leave the orbit of their hotel. The Red Sea is spectacular, the dive boats line the horizon, and the logistics are frictionless. It’s easy to stay put.

That’s not me, however. All regions of the world are worth visiting, so I needed a way to “do Sharm” on my own terms.

I hired a local guide and told her I wanted to understand her city. What followed was four hours that fundamentally altered my perception of a place I might otherwise have written off as “just another resort town.”

We started in neighborhoods where young Egyptians sat in hillside cafés overlooking the water, drinking tea and talking long into the afternoon. Sure, this place becomes filled with tourists and DJs in the evening, but during the day? Lots of locals just relaxing and enjoying the seaside.

We visited the largest church in Sharm: quiet, grounded, woven into the rhythms of local life rather than tourist itineraries.

I also marveled at the domes of a mosque rising into that stark blue Sinai sky, a reminder that Sharm is not simply a vacation product. It is a city layered with religious, social, and economic complexity.

Yes, Sharm was built with tourism in mind. But that is only one layer of its identity. The deeper story is there for anyone willing to step beyond the perimeter wall.

Hurghada: When the Script Gets Scrapped

Hurghada carries a similar reputation. All-inclusive central. European sunseekers. Predictable experiences. Nothing to intrude upon your chill time.

I hired a guide there as well, expecting a structured program. I’d been promised a list of sites we’d see. Within ten minutes he looked at me and said, “You don’t want the normal program, do you? Can I show you what I think you’ll like?”

He was right.

We scrapped the script.

Instead of polished stops designed for visitors, he took me to the mosque locals actually attend.

He brought me to the fish market where families negotiated dinner in real time, surrounded by ice and salt and the smell of the sea. He even found a giant crab which was apparently uncommon, and asked me if I minded him taking the time to buy his dinner. Are you kidding? Watching how locals interact and haggle? I’m SO in!

We stopped at a church tucked quietly behind greenery and traffic barriers — not as an attraction, but as part of the city’s living fabric.

By the end of the afternoon, I didn’t feel like I had toured Hurghada. I felt like I had been introduced to it. There is a profound difference between being shown a place and being welcomed into it.

That difference requires intention, and often just a simple question: “What do you think I should see?”

Papeete: Paradise and Payroll

Tahiti exists in most peoples’ imaginations as turquoise lagoons. Overwater bungalows. Honeymoon-central in its most pure form.

And it is beautiful. Don’t get me wrong.

But no paradise sustains itself on scenery alone.

Behind every resort are workers who commute. Groceries that need stocking. Children going to school. Policies debated in government chambers.

So in Papeete, I wandered. No guide this time. Just curiosity.

I walked through the local market where fruit was stacked high, labeled in Pacific francs, purchased by people who weren’t on vacation.

I passed the Assembly building, where decisions shaping French Polynesia’s future are made.

paused at the fish market, watching today’s catch laid out for locals who will cook it for family dinner — not for Instagram. And yes, I still stood by the water and absorbed the surreal calm that makes the Pacific feel almost engineered.

The difference was not the destination. It was the decision to look past the postcard.

The Choice

You can travel 8,000 miles and learn almost nothing. Relax, recharge, but not reflect.

Or you can walk 800 meters outside your hotel gate and recalibrate how you see the world.

Tourist infrastructure is not inherently shallow. It simply makes it easier not to engage. It offers comfort, efficiency, predictability. If that is what you seek, you will find it effortlessly.

But if you want connection…you have to do some work. We’ve all heard over and over that nothing worth having is easy.

You have to hire the guide.
You have to ask the questions.
You have to wander without a guarantee.
You have to accept mild inconvenience as the price of insight.

The return on that effort is exponential.

In Hurghada, I left with a local friend, not just a memory.
In Sharm, I saw the day to day tedium and normal life rarely mentioned in travel forums. In Papeete, I was reminded that even the most idyllic places are sustained by ordinary people living ordinary lives.

And that, to me, is the magic.

Not in rejecting resorts. Not in pretending leisure is beneath me. But in refusing to let the curated version be the only version.

These places are what you make them.

Consumption and relaxation are easy, connection takes intention.

The destination doesn’t decide which one you experience…you do.

Abyei is one of them.

Technically, it is not a country…not ONE country at least. It is not fully Sudan. It is not fully South Sudan. It is a condominium: a territory claimed by both nations and administered under special arrangements after South Sudan’s independence in 2011. For decades, it has been politically disputed: oil reserves, migration routes, ethnic tensions, and the kind of colonial-era border decisions that continue to age badly.

On paper, Abyei reads like a hot mess.

In person, it reads richer than I’d ever imagined.

How We Got There

I was fortunate to visit with an exceptionally well-traveled group of folks from Most Traveled People (MTP), a global community of travelers who don’t just chase passport stamps but the edges of maps. (If you’re curious click the link!)

We chartered a small plane into Agok airstrip, a dirt lane of gravel and dust that feels more like a hastily-assembled afterthought than real infrastructure.

From there, it was a few-hour drive over some of the worst “roads” I’ve ever traveled into Abyei town. No dramatic border arch. No cinematic checkpoint scene. Just open land and the quiet awareness that you’ve entered one of the world’s most politically ambiguous spaces. And then…almost instantly…“Abyei” stopped being a headline and became names, faces, and laughter.

The History Everyone Quotes

Abyei sits between Sudan and South Sudan and has long been contested. The region is home primarily to the Ngok Dinka people, while Misseriya pastoralists from the north migrate seasonally through the area. When South Sudan voted for independence in 2011, Abyei’s own referendum on whether to join Sudan or South Sudan was never fully implemented. Tensions escalated. Armed clashes occurred. Political agreements stalled.

The United Nations maintains a peacekeeping mission here, and several of the soldiers were kind enough to share their stories with us. Now let this sink in: disputed conflict zone and who are the peacekeepers? Indians and Pakistanis. Working side by side to REDUCE conflict. Sometimes you have to come to the “ends” of the Earth to find solutions that should be painfully obvious.

There are signs all over Abyei declaring the area weapons-free. Given we had a security detailed that was rather well-armed this felt like more of a suggestion than a rule.

All of that is real. All of it matters.

But it’s not the whole story.

What You Actually See

Walk through Abyei town and you don’t walk into a battlefield. You walk into a living, breathing mass of humans living life day to day.

Livestock move through the dust like they own the place…because they do.

Trucks unload goods. Vendors negotiate. Goats yeet themselves through strewn rubbish like chaotic interns hyped up on caffeine.

Children gather around you, curious and amused. They ask where you’re from, why you’re there. They’re genuinely curious in that honest way only children can be.

Women prepare food over charcoal stoves in small roadside restaurants, chopping greens and boiling water in dented kettles as thick smoke curls toward corrugated metal roofs.

A nearby waterway cuts through the landscape, quiet and indifferent to political theory.

As we settled down for the night in our compound (complete with armed guards) I went for a run through Abyei town that evening (yes, I actually wanted to keep my running streak alive THAT much) as the sky softened and kids played in the potholed roads. The best part? Kids were amazed…and ran after us…and with us. It was magical. It was ALIVE.

If you only knew Abyei from headlines, that image probably wouldn’t compute.

But that’s the point.

The Part the Media Rarely Shows

Conflict zones are often presented as static and singular, defined entirely by instability. And yes, the political fragility here is real. The tension is not theoretical. But even in a place like Abyei, normal life does not wait for perfect governance.

Kids go to school.
People open shops.
Families argue about dinner.
Someone worries about exam results.
Someone laughs.

The extraordinary thing about humanity is how stubbornly ordinary it remains.

That’s the part that rarely makes it into the evening news. Because normalcy doesn’t trend. It doesn’t spike engagement. It doesn’t slap as hard as crisis footage.

But it’s 99% of what we experience in our short time on this spinning blue marble.

And that’s why I travel.

Not to collect danger points. Not to cosplay as a war correspondent. But to experience places firsthand and form my own understanding: beyond the algorithm, beyond the headline, beyond the narrative I’m handed.

When you stand in a place labeled “disputed” and watch someone stir a pot over charcoal while a kid chases a tire down the road, something recalibrates. The world becomes more complex…and infinitely more human.

You realize how much of your perception has been pre-packaged.

And how much richer reality really is when you experience it for yourself.

Practical Notes for Visiting Sensitive Regions

If you’re considering travel to politically fragile or disputed areas:

• Go with experienced operators who understand the security dynamics.

• Respect local people…you are a guest, not an anthropologist on safari.

• Avoid sensationalizing what you see.

• Listen and look way more than you talk.

• Remember that “fragile” does not mean “void of normal life.”

Travel will not solve geopolitical disputes.

But it will solve something in you.

It replaces abstraction with experience. It replaces assumption with nuance. It reminds you that even in the in-between spaces of the map, life persists: stubbornly, beautifully, and very much off-camera.

And honestly?

That perspective hits harder than any headline ever could.

Feedback is welcome. If this format slaps, tell me. If it’s cringe, also tell me (gently).

Because today’s topic is basically this: touristy places can be annoying as hell… and still absolutely worth it.

Think Paris: Eiffel Tower, Louvre. Rome: Colosseum. Beijing: Great Wall. You know the scene: tour buses pulling up like it’s a conveyor belt, people sprinting off for a quick selfie, and then reloading back onto the bus like they’re speedrunning human history.

There is a lot to dislike.

Crowds. Noise. Tripods and Selfie Sticks. “Main character energy” glamor shoots blocking the entire walkway. The air of urgency, like everyone’s trying to “complete” the destination instead of experience it.

I wrote about one way to mitigate this in The Case for Bad Timing: go early, go late, go in the rain, go when the algorithm is asleep. Sometimes it works beautifully.

And sometimes it doesn’t. Or it’s just not practical.

Sometimes the place is just popular for a reason, and you are going to be in there with 200 other sweaty mammals breathing the same ancient air.

Which brings us to Luxor, Egypt, and the Valley of the Kings.

The Valley of the Kings: Why It’s a Big Deal

If you have never been, here’s the simplest explanation: the Valley of the Kings is essentially the Egyptian New Kingdom’s VIP afterlife hood, carved into the desert hills on the west bank of Luxor. Pharaohs (and other royals) were buried here in elaborately painted tombs designed to help them navigate the underworld and arrive safely in the next life.

This is not “look at a ruin” travel. This is “walk into a sealed, painted time capsule” travel.

Almost all of the tombs you can visit are underground, and the walls are covered top to bottom with scenes, symbols, and hieroglyphs that still pop with color in a way that feels unfair. Like… how is this still this vivid after more than 3,500 years?

But here’s the catch: not all tombs are open, and the open ones rotate. Your standard ticket usually includes entry to four of the open tombs of your choice, and then there are paid add-ons.

And yes, this is where travel logistics meets travel psychology.

Because the tombs that cost extra (like King Tut, and some of the big-name Ramses tombs) tend to be less crowded for the simple reason that a portion of the tour groups skip them.

Not all, but enough that you feel the difference.

Which is funny, if you think about it: sometimes the path to a more peaceful experience is just… paying for the premium DLC.

The Crowd Problem (and Why You Still Go)

Let’s talk about the thing everyone complains about in the Valley of the Kings: crowds in the tombs.

Some tombs are calm. You can stand there, take your time, actually see what you’re looking at, and feel that hush that hits when you realize you’re in a place built for eternity.

Other tombs are… a sweaty, gross, humid group project.

Tight corridors. People squeezing past each other. The air gets thick. You can smell the collective effort. Someone’s flashlight is blasting the wall art like it owes them money. Another person is narrating loudly for their entire group like they’re hosting a live podcast called I Am The Only Person Here. The only upside? Tour guides are NOT allowed to narrate inside, so at least you only have to deal with the other visitors.

And even then?

It’s still worth it.

Because here’s the part that snaps on the internet cannot replicate: scale and presence.

You can look at photos of tomb art online all day. You can zoom in. You can read the labels. You can “learn.”

But you cannot download the feeling of standing in a space carved by hand thousands of years ago, where the walls were painted for a king who genuinely believed these images could guide his soul through the afterlife.

You go because your body needs to be there to understand it.

A Note on “Must-See” Places (and Staying Sane)

I know I sound like I’m defending tourist chaos, and I kind of am, but with conditions.

The goal is not to pretend crowds are magical.

The goal is to keep perspective and remember why you are there.

You are not there to win travel. You are not there to prove you were there. You are there to experience something real, and ancient, and wildly human.

The trick is learning to tune people out without becoming inconsiderate yourself.

There is a difference between:

• “I’m going to focus on the walls and ignore the noise,” and

• “I’m going to block the hallway for 12 minutes so I can get the perfect shot while everyone else suffers.”

The first is Zen. The second is villain behavior. Leave that to others.

If you mentally prepare for crowds, and decide ahead of time that you will not let other people’s chaos hijack your moment, you can still have an incredible experience.

Not perfect. Not empty. Not cinematic.

But real.

And honestly, real is better.

King Tut: Yes, It Costs More. Yes, You Should Do It.

Alright, let’s address the big one.

That stone-hard dude in the glass case is actually King Tut. That alone is enough to make some people feel weird, and I get it. It is a human being. A young king. A real body. Not a museum “object.”

But that confrontation is also part of why it matters.

Tutankhamun’s tomb is famously small compared to many others, but it’s iconic because of what his discovery represented and how it reshaped the world’s obsession with ancient Egypt. King Tut became king early, and died a few years later, so there just wasn’t much time to build him an elaborate tomb like many others. Seeing it in person, and then seeing him, is a reminder that history is not an abstraction. It was people.

It also tends to be less crowded because it is a $10+ add-on, and the tour bus herd doesn’t always stampede in.

Which means you actually get a moment.

The “Bangin Pics” Reality, Even in Peak Chaos

One of the funniest parts of places like this is that you can walk into a packed tomb and still come out with photos that look like you had the place to yourself.

Not because you were being inconsiderate. Not because you shoved someone out of frame.

But because the walls are so visually overwhelming that if you’re patient for ten seconds, the moment opens up. People shift. Someone steps back. The corridor breathes.

And suddenly you’re getting shots that look like the tomb rolled out the red carpet for you personally.

The Philosophy Part: You Can Have It All (But You Have to Choose Your Mindset)

Here’s the point I keep returning to, especially in high-crowd, high-hype places:

You really can have it all.

You can see the famous places and still travel thoughtfully.
You can appreciate the masterpieces and refuse to be consumed by the madness around them.
You can be present and still take the photo.

But you have to prepare your head for it.

If you walk into the Valley of the Kings expecting solitude, you will be miserable.

If you walk in expecting crowds but committed to your own experience anyway, you get the gift: the ability to stand inside something thousands of years old and feel, for a second, like time is bigger than your schedule.

And that is the entire reason we travel in the first place.

Quick Tips: Making Iconic Crowded Places Actually Work for You

Before you scroll to the CTA, here’s how to make places like the Valley of the Kings hit the way they’re supposed to:

• Mentally expect crowds. If you expect solitude, you’ll be annoyed. If you expect chaos, anything better feels like a win.

• Pay for the add-ons. The extra tombs (King Tut, Ramses) cost more for a reason. Fewer tour groups = more breathing room.

• Pause instead of pushing. Ten seconds of patience can clear a frame, open a corridor, and change your entire experience.

• Focus on one wall, not the whole room. Depth beats overwhelmed. Let your brain zoom in.

• Don’t become the villain. Tune people out internally, but never block the space externally. Be best. (groan)

You can’t control the crowd.
You can control your mindset.

And that changes everything.

“There are known knowns; there are things we know that we know.
There are known unknowns; that is to say, there are things that we know we do not know.
But there are also unknown unknowns; the ones we don’t know we don’t know.”

It is one of the most unintentionally profound quotes ever uttered in a press briefing, and whether Donald Rumsfeld meant it philosophically or not, it absolutely nails something fundamental about travel.

If you never leave the place you were born or grew up, your world is almost entirely made up of known knowns and known unknowns. You know how things work where you live. You know what people are like. You know what success looks like. You also know what you think you don’t know, because television, social media, and headlines have already handed you a pre-packaged version of the rest of the world.

But unknown unknowns?
Those only show up when you actually get out of your comfort zone and physically go somewhere else.

Travel is the fastest and best way I know to discover that large parts of reality were never even on your radar.

When you cross a border, especially one you were taught to think about in abstract terms, something shifts. You stop consuming other people’s interpretations of a place and start forming your own. The smells are different. The rhythm of the day is different. The way people interact, argue, relax, and move through public space is different.

Suddenly, things you assumed were universal turn out to be very local.

And no documentary, podcast, or think piece can replicate that moment when your brain quietly goes, “Oh. I didn’t know this was even a thing.”

That is the unknown unknown revealing itself.

A lot of people wonder whether travel is about liking everything you encounter. It absolutely is not. You will be uncomfortable sometimes. You will disagree with things. You will encounter systems, norms, and ideas that do not align with your own.

Many of us are perfectly content to only expose ourselves to people who think, act, and value the same things we do; that’s human nature. That is not a failure of travel. That is the point.

Since the dawn of time humans have sought out the familiar, and there’s nothing wrong with that. What is wrong, however, is limiting your entire world and life to that. If you only ever seek out places that perfectly mirror your existing beliefs, you are not expanding your worldview. You are just reinforcing it, albeit with better scenery.

Travel does not promise comfort. It promises contrast.

And contrast is what sharpens perspective.

There is also something deeply grounding about realizing how much of what you “know” was never firsthand. When you are at home, your opinions are often assembled from secondhand material. Someone else’s outrage. Someone else’s fear. Someone else’s framing.

When you are on the ground, those borrowed narratives start to fall apart.

You start to notice the ordinary humanity underneath the abstractions. People going to work. People laughing. People annoyed about the same mundane things you are annoyed about. Life continuing, regardless of how dramatic it looks from the outside.

That realization tends to make you a little humbler and a lot more curious.

Which, frankly, is a pretty great trade.

Will you come home with neat and crystal-clear answers? Rarely. More often, you come home with better questions. Questions about why things are done the way they are. Questions about what you were taught to assume. Questions about whether your way is the only way, or even the best way.

That is what happens when unknown unknowns become known. Your mental map of the world gets bigger, messier, and more interesting.

You do not need to agree with everything you encounter. You just need to encounter it honestly.

Because living entirely inside someone else’s version of the world is easy. Shaping your own understanding takes effort, movement, and a willingness to be wrong sometimes.

And yes, that can be uncomfortable.

But it also makes life richer, sharper, and far more real.

I arrived expecting something heavier and more visibly post-Communist, more austere, more stuck in its past. Instead, what I found was a city that celebrates its history without letting it dominate the present.

Yes, Albania’s communist era is weird AF and impossible to ignore. But Tirana doesn’t feel frozen in it. It feels forward-looking, energetic, and unexpectedly modern…the kind of place that’s actively deciding what it wants to be next.

And that decision is happening in real time.

Bunkers Bunkers Everywhere (And What They’ve Become)

Albania is famously dotted with concrete bunkers (tens of thousands of them) built during Enver Hoxha’s paranoid dictatorship. Tirana doesn’t hide this history. It curates it.

Bunk’Art 2 sits beneath Skanderbeg Square and drops you straight into Albania’s communist past. It’s unsettling, informative, and well done…not sensational, not softened.

Bunk’Art 1 is larger, deeper, and more immersive, a full underground complex that once housed top officials in the event of nuclear war. One of the employees told us that despite how huge it is, and how many levels we saw, less than 20% of it is actually open to the public.

This desk belonged to Hoxha himself. Seeing it underground, surrounded by concrete walls, really drives home the isolation and fear that defined the regime.

The House of Leaves museum might be the most chilling stop we saw on our trip through Tirana. Entire rooms devoted to surveillance tech used on ordinary people: neighbors, coworkers, even family members.

It’s not just history. It’s a reminder of how fragile privacy really is.

A City Reinventing Itself Through Architecture

What truly caught me off guard was how architecturally ambitious Tirana has become. Bold shapes, modern materials, and a refusal to play it safe.

This building feels intentionally global, the kind of design you’d expect in Western Europe, not something clinging to the past.

The contrast works. Communist-era blocks sit next to sleek new towers without apology.

There’s a sense that the city is experimenting, testing ideas, and not afraid of a little controversy.

Skanderbeg Square & the City’s Core

Everything eventually leads back to Skanderbeg Square: wide, open, and very alive.

This isn’t a square you rush through. People linger. Kids play. Locals meet friends. It feels genuinely civic, not performative. A place local people (and an increasing number of tourists) pass through on the way from one place to another, but often linger because you can’t help run into someone you know.

Faith, Identity, and Mother Teresa

Religion here feels present but not overpowering, part of the city’s identity rather than its headline.

Mother Teresa (Nënë Tereza) was Albanian by ethnicity, and her legacy is woven into Tirana with respect rather than spectacle.

Inside, it’s peaceful. Simple. A pause button for reflection in the middle of the city.

The River Running Through It All

Tirana has a river that doesn’t try to be romantic…and that’s kind of the point.

It cuts through the city like infrastructure, not decoration. Walkable paths, greenery, locals going about their day.

Food That Locals Actually Love

Tirana’s restaurant scene is incredibly strong…especially if you want food that feels both local and familiar.

Era has two locations and both are packed for a reason. Italian influence, Albanian ingredients, and consistently good execution. So good we ate at both of them, and wanted to come back for more.

Think fresh pasta, grilled meats, local wines…the kind of place locals bring visiting friends.

(Seriously, don’t skip it. Reservations help…and you can sit outside at the larger location or inside in the smoke-free dining room…rare for Tirana but much-appreciated!)

The Real Highlight: The People

More than the museums, the buildings, or the food it was the people.

Friendly without being intrusive. Curious without being performative. Genuinely helpful in a way that feels natural, not transactional.

Directions turned into conversations. Questions turned into recommendations. It made the city feel welcoming in a way that can’t be engineered.

Final Take

Tirana doesn’t deny its past, it contextualizes it. Then it builds forward.

It feels European, modern, creative, and alive, far removed from the gray, closed-off version many people still imagine when they think of Albania.

This city is not stuck.

It’s evolving, and it’s worth your time.

1. the itinerary people: spreadsheets, pins, time blocks, backup plans for the backup plans, every little detail picked out in advance

2. the wing-it crowd: vibes, caffeine, one too many cafés for a glass of wine, trips unfolding by divine intervention

3. the “just drop me at a resort or on a ship and don’t ask questions while I enjoy another umbrella drink” contingent (no shade, just… not my lane)

I’ve spent most of my travel life somewhere between the first two.
But here’s the nuance that I don’t always perfectly express when I’m telling my travel story:

Yes, I’m a list person.
Just… not a list of must-see-sites person.

My type of lists were never “Mona Lisa at 10:15, Colosseum at 2:30.”
They were countries. regions. routes. how far the map could stretch if I challenged it hard enough.

I liked the macro challenge. The puzzle. The obsession.
Which is probably how I ended up in every country on Earth without ever caring that much about standing in line for the same photo everyone else already has.

And over time…slowly, stubbornly…I learned something important about myself:

You can absolutely do travel.
But if you’re not at least a little deliberate about it, you won’t actually experience it.

The problem with checklist travel isn’t that it’s wrong.
It’s that it quietly turns travel into somewhat of a job or a chore.

You move fast. You collect proof. You optimize.
You feel productive…which, honestly, is very on-brand for modern life.

But the moments that stay with you?
They almost never happen on schedule.

They happen when you sit too long at a café and chat up a group of students who want to improve their english.
When a “quick stop” turns into a conversation with the eccentric old man and his tiny dog who live down the street and want to tell you every detail of their life in this neighborhood.
When you’re not rushing, not documenting, not mentally checking the next box.

The wild part?
Most people’s favorite travel memories don’t involve the thing they planned hardest.

Nobody comes home glowing about:

• the hours in line

• the crowds

• the timed entry ticket they fought for online

They come home glowing about people.
About stories. About moments that were never anticipated or planned for.

And yes, before anyone panics, landmarks are incredible. They’re iconic for a reason.

Standing in front of something ancient, iconic, almost mythic? Still hits. Still slaps hard.

But here’s the quiet shift that happens once you’ve traveled enough and done a bit of introspection about why you love to travel:

Seeing becomes easy.
Being present becomes the flex.

The internet has made visuals cheap.
What it hasn’t made cheap is genuine human connection.

You can Google a photo of anything.
You can’t Google what it feels like to linger somewhere long enough to let it sink in and become part of the local tapestry.

This is usually where someone says,
“But if I don’t plan, I’ll miss everything.”

Here’s the reframe:
You’re going to miss things. Always. That’s part of life.

You could live in one city for a year and still miss things. I lived in the Washington, D.C. area for 30 years and there’s still a huge list of things I’ve never seen.

The goal isn’t completion. The goal is depth.

Ask yourself this instead:
Do I want to feel like I did this place…or like I met it and lived it?

Because the deeper travel gets, the less it’s about trophies and the more it’s about texture.

Nobody leans in when you say, “I checked off everything.” (well, maybe a little)

People lean in when you say:

• “I met this person who…”

• “We ended up somewhere totally random…”

• “You won’t believe this shit…”

That’s the travel glow.
That’s the stuff that rewires you.

So… are itineraries a good idea?

Sometimes. For some people. On some trips. Or at least some parts of some trips.

But if you want travel to feel expansive instead of exhausting, here’s the move:

Think of your itinerary as a loose framework, not something that dictates every move you make. It should give you a sense of direction without boxing you in or rushing you past the moments that actually matter.

Leave room for the trip to clap back at your expectations.

5 hot tips for traveling beyond the checklist

1. Anchor, don’t overload.
   One meaningful plan per day. Everything else is gravy.

2. Demote must-sees to cameos.
   Let landmarks be part of the day, not the whole plot.

3. Live where locals live.
   Residential neighborhoods > tourist cores. Always.

4. Schedule nothing (yes, literally).
   Protect unplanned time like it’s sacred. It kind of is.

5. Measure trips in stories, not stamps.
   If you come home changed, you did it right.

For centuries, this lake has been a cultural crossroads: Orthodox monasteries, Roman roads, Ottoman influences, Yugoslav history, and Albania doing its famously weird communist thing just across the water. Borders here have shifted. Empires have come and gone. The lake? Completely unbothered.

I recently visited the town of Ohrid, North Macedonia in winter and drove the full loop around the lake , and honestly? I think winter might be the cheat code.

Winter in Ohrid = The Cheat Code

Winter is still very much a good time to go.

Fewer people. Better prices. Restaurants actually want to talk to you. Local life isn’t hidden behind tour groups. The lake takes on a softer, calmer personality…less postcard, more presence.

Yes, it’s cold. Yes, some places close early. But the tradeoff is space, stillness, and the feeling that the town belongs to the people who live there…not just the people passing through.

Where We Stayed (And Why It Worked)

Instead of a hotel (no chains here, just some smaller local ones), we rented a small apartment up the hill overlooking the lake. It was quiet, walkable, and gave us views no lakeside hotel could match.

Every morning started with the lake spread out below us. Every night felt like coming home instead of returning to accommodation.

Highly recommend this route. If you want the contact, hit me up. They were incredible hosts and helped us find parking for our (way too big) rental car, and escorted us out of town the next morning through all the narrow and winding roads, clearing the way for us. As always, it’s the people who make the place special!

Eating Your Way Through Ohrid

Ohrid is a place where food still follows seasons and geography.

You’ll eat well everywhere, but Restaurant Sv. Sofija is a standout.

Order the Lake Ohrid trout. It’s local, carefully regulated (and double the price of the frozen trout on the menu), and prepared with just enough restraint to let the fish shine. Pair it with a local red wine. Take your time. Nobody’s rushing you.

The Town Itself (Statues, Squares, and Zero Rush)

Ohrid is layered with churches, statues, parks, and open squares. Not in a “museum city” way — more like a place where history just…exists alongside daily life.

In winter, you notice things you’d miss in summer: conversations echoing across plazas, kids kicking balls through empty squares, café owners lingering instead of hustling.

The Cats (Yes, We’re Talking About the Cats)

Ohrid has a lot of cats. Not feral-chaos cats — well-fed, social, “this is my city” cats.

They nap on warm stone steps, patrol café patios, and accept affection like it’s rent. The cats are part of the ecosystem. Respect them. They were here first.

Driving the Lake (Do Not Skip This)

Drive the full loop if you can and explore from both the Albanian and North Macedonian sides of the lake.

The road hugs the water, slips through forests, passes tiny villages, and constantly reminds you that slowing down is the entire point. Stop often. Wander. Let curiosity win.

St. Naum: Where Things Get Slightly Magical

St. Naum Monastery sits on the Macedonian side of the lake near the Albanian border and feels worlds away from town.

It’s peaceful, green, and quietly surreal. Spring-fed waters. Wooden walkways. Time moving differently.

And yes…

The peacocks live here. They scream. They pose. They do not care about your schedule.

Winter Villages & Old-School Vibes

Winter driving means you’ll pass through villages untouched by tourism that time of year.

Shops open when they feel like it. Old communist-era cars still roam the streets. Life continues without performance. It’s refreshingly real.

Top 5 Tips for Lake Ohrid (Winter Edition)

1. Go in winter — fewer tourists, better prices, deeper experience.

2. Rent an apartment — views, space, and the feeling of actually living there.

3. Eat local trout — especially at Sv. Sofija. Trust me.

4. Drive the lake — St. Naum and the villages are the soul of the region.

5. Pet the cats (politely) — they are cultural ambassadors.

Waiting for the right time. Waiting for more money.
Waiting for fewer responsibilities. Waiting to be braver, richer, freer, more qualified.

“If I won the lottery…”
“When I retire…”
“If work slowed down…”
“If the kids were older…”
“If I had more time…”

We build entire imaginary lives on top of that word: if.

But travel has taught me something simple and deeply uncomfortable: most of the time, it’s not some massive transformation that separates us from the life we want. It’s one small change we’re avoiding because it feels inconvenient, uncomfortable, or just unfamiliar.

For me, that one small change happened when I was sixteen.

I left North America for the first time to study in the USSR. No soft launch. No easing into it. Just yeeted myself straight into the deep end. That single decision flipped a switch. I went from spending hours every week paging through the Official Airline Guide (yes, that OAG…pre-internet travel geek kids know) fantasizing about faraway places…to eventually building a life where travel wasn’t a dream, it was the default.

One choice. One yes. One crack in the “this is how life works” narrative.

Everything else followed.

Travel tends to expose how often we wait for permission that never comes.

We tell ourselves we’ll start living after something happens: more money, more stability, fewer risks…but the truth is, clarity rarely comes first. Momentum does. The smallest change creates movement, and movement creates options you couldn’t see while standing still.

Life doesn’t usually open doors with a grand gesture. It cracks a window and waits to see if you’ll push it wider and let the sun shine in.

Travel may be my world, but this isn’t really about travel. It’s about refusing to let if run the show.

So here’s the question I’ll leave you with this week:

What’s the one small change you keep postponing? The one that might quietly change everything?

Because mountains don’t disappear.
They just turn into opportunities once you start climbing

Some of my most memorable travel moments have happened when I did things at the wrong time.

Not reckless-wrong. Not inconvenient for the sake of being edgy.
Just slightly off the schedule everyone else seems to follow.

Pisa, After Everyone Went Home

Like usual, I was trying to do too much.

I had built a trip that made perfect sense on paper and absolutely no sense in reality. (I swear, I didn’t use ChatGPT and it’s notorious inability to try and cram too much in to plan it!) I was running out of hours and had two choices: skip something I genuinely wanted to see, or find a way to stretch the day just a little longer.

So I did what might apparently become my new default solution to everything: I went for a run, ate dinner, and then took a 7pm train to Pisa.

No sunrise alarm. No golden hour photo chasing.
Just…after dark.

By the time I arrived, the city felt like it had closed up shop for the day. The river reflected light instead of noise. Streets were still alive to a different degree, but unhurried. It wasn’t empty, it was simply no longer trying to accommodate anyone and everyone.

And when I finally reached the “Field of Miracles”, it hit me how different the experience felt.

There it was. Leaning, iconic, and completely unconcerned with being admired.

No crowds pressing forward. No choreography of photos (although I did catch one couple still trying to do the iconic “holding up the tower” pose). No sense that I needed to hurry up and “get it done.” I could walk slowly. I could circle it. I could stop taking photos and just look.

For once, the Tower wasn’t competing with the experience around it.

I don’t really subscribe to the idea of “must-see” places. Travel shouldn’t be a checklist. But let’s be honest: some places are famous because they genuinely deserve to be.

They take your breath away.

They just do it more quietly when you’re not sharing the moment with thousands of other people doing the exact same thing at the exact same time.

Not better than anyone else’s experience. Just better for me.

Night Isn’t the Only “Wrong” Time

This idea isn’t limited to going places after dark.

It’s about choosing moments when destinations aren’t optimized for visitors, when the experiences and stories you encounter are shaped more by local life than by demand.

That might mean traveling through Europe in winter once you look beyond skiing and Christmas markets. Or visiting somewhere like Dubai in July, when the temperature hits 45°C and you start to understand how people actually adapt, slow down, and live within the extremes rather than escaping them.

Weather changes behavior.
Timing changes tone.
And the “wrong” season often reveals what the “right” one hides.

When you go at the “wrong” time, you stop chasing highlights and start noticing details. Who is still out walking. Which cafés and restaurants are open because they’re part of daily life, not because they’re trending. How cities function when they’re not being consumed.

That’s when places stop feeling like destinations and start feeling like communities.

This Isn’t About Avoiding People

This isn’t anti-tourism, and it’s definitely not about gatekeeping experiences.

Travel is a privilege, and it’s a good thing that more people than ever get to see the world. But authenticity doesn’t come from being first or alone, it comes from timing, patience, and the willingness to step slightly outside the obvious plan.

Go later.
Go colder.
Go hotter.
Go when the schedule says you shouldn’t.

Because sometimes the most meaningful travel moments happen when you stop optimizing and simply show up: after the crowds, after the noise, after the checklist goes quiet.

For me, that night in Pisa sealed it.

I think this might be my favorite way to see famous places going forward.

After dinner.
After dark.
After everything else has settled.

Because at some point, whether we’re talking about travel or life (and I find travel to be an amazing metaphor for life), we all face the same fork in the road. We can sit still and wait for life to happen to us…or we can get up and go meet it halfway.

The more I travel, the more I find this isn’t really a question at all; human nature is to wander, to explore, to satisfy our curiosity….to live.

“The woods are lovely, dark and deep,
But I have promises to keep,
And miles to go before I sleep,
And miles to go before I sleep.”
—Robert Frost, Stopping by Woods on a Snowy Evening

It’s easy to stay put. Familiar routines are comfortable. Predictable. Safe. But as one of my favourite lines from Dead Poets Society wisely said, “No matter what anybody tells you, words and ideas can change the world.” Travel does that; it introduces new ideas simply by forcing you to move your feet.

You don’t have to blow up your life overnight. You just have to start asking better questions.

We all start out curious. Kids are the world’s natural-born explorers: asking questions, sticking things in their mouthes they probably shouldn’t, and wandering off without a plan. Somewhere along the way, curiosity gets labeled as impractical. Responsibility creeps in. Schedules harden. “Someday” becomes a holding pattern.

But as Ferris Bueller warned us (very politely, all things considered): “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”

Travel forces us to stop. To have a look around.

The unexamined life isn’t dangerous, it’s just…quiet. And sometimes quiet is exactly what keeps us from noticing what else might be possible.

Every trip I’ve taken that has stuck with me and made me who I am started the same way: mild discomfort, unanswered questions, and the nagging sense that staying put would’ve been easier.

Easier, yes. Better? Rarely.

So here’s the only question that really matters:

What are you waiting for?

Permission? Perfect timing? Fewer responsibilities? More certainty?

Travel has taught me that none of those things arrive first. Movement does.

You don’t have to seize the day.
You just have to stop postponing it.

And sometimes, the first simple step forward is all it takes.