We Travel at a Moment in Time

You might worry your sabbatical plans aren’t quite “right.” It’s not adventurous enough or not Instagrammable enough or missing a bunch of destinations or so full of destinations you can’t stay the whole summer in Positano like you originally dreamed about, or, or, or… On the other hand, you might love your sabbatical itinerary and think it’s completely perfect but you’re scared something will happen on the road to screw it all up. Here’s an insight that I think will help you embrace a key aspect of travel: we travel at a moment in time.

You can’t plan it all. You’re not just planning a trip; you’re planning a series of moments. And each of those moments will be shaped by who you are, what you need, and what the world looks like when you finally board that one-way flight.

The Unrepeatable Nature of Travel

The same city can feel completely different depending on when you go, who you meet, or what season of life you’re in. At the end of the day, we’re really chasing experiences and there are elements of that we just can’t plan.

This is one of the most beautiful and bittersweet lessons of long-term travel: you can never have the exact same experience twice. But that’s so much of what makes it worthwhile.

I’m hoping this particularly helps anyone who is torn about revisiting a place on your sabbatical that you’ve already been to. You could return to the same destination five times and have five completely different experiences. Maybe you visit in a different season or stay in a different neighborhood. Maybe you have a longer stay this visit and there’s time to go off the beaten path or explore things you didn’t get around to last time. Or there might be something totally different about the destination itself.

Destinations Don’t Exist in a Vacuum

Even the most iconic places with timeless-seeming attractions exist within a particular context at any given point in time.

I’ve been to Paris three times. The most recent trip, Notre Dame was still closed for renovations. When I go again, the beautifully restored building will look nothing like the dark, dirty church I saw as a teenager. And in the meantime, I got to see two newly renovated museums.

I’ve been to Rome and the Vatican more than once… usually there’s a pope, but my first time, there wasn’t. I just barely managed to squeak in a visit to the Sistine Chapel before it closed for conclave. Added bonus: soon after, I had a phone call with my grandmother and found out when she first visited Rome in the 1950s, they were between popes then too!

I landed in Bangkok during a year of mourning for King Bhumibol Adulyadej. There were murals all over the city and crowds of mourners at the Royal Palace. At the time, I wasn’t sure whether the royal anthem playing before a movie was part of the mourning period or not, but it turns out this is an everyday occurrence.

I’ve been amid multiple cities’ excited countdowns to hosting the Olympics. Felt the dread across former communist countries in Eastern Europe as Putin threatened Ukraine. Seen countless places struggle with development, gentrification, and overtourism. As crowded as Galway looked on a Sunday afternoon to me in 2024, I know that a new port docking four cruise ships a day will make any future visits I pay feel very different to that first ever day I spent there.

Local elections, protests, and strikes may impact your travels. Construction, weather, or any other number of changes. But I hope knowing this about travel defangs some of the frustration that can come from aspects of the world we can’t control.

This is part of your travel experience too. As are the people you meet.

People Make the Place

When you think about the highlights of your past travels, how many of them are actually about people?

The friend you made on a group tour (or, ok… maybe it was a pub crawl). The guesthouse owner who welcomed you like a niece from out of town (and thought you really need to eat more, you look so skinny). The stranger who gave you directions and saved the rest of your day. The version of yourself that emerged in a totally new place.

People — whether they’re locals creating the community worth going to or fellow travelers adding their own perspectives and magic — are what give travel its emotional weight. And those people aren’t static either. Their timelines, like yours, are always shifting.

Sometimes you arrive in a city at just the right moment, when you’re ready to slow down, or take a risk, or open up to someone new.

Who you meet shapes your travel experience and there’s no way to prepare for that in advance.

There’s No Perfect Itinerary

If you’re planning a sabbatical and feeling the pressure to get every detail “just right,” it helps to remember this: travel is inherently imperfect. And the unplannable stuff is part of its magic.

You don’t need to see every highlight or check off every box to make this trip meaningful. You need a framework for planning what you can, so that on the actual trip you can show up for the version of the world — and the version of yourself — that exists in that particular moment.

Because it will never come again in quite the same way.