FEATURE STORY
I'm the first one to say it. There are too many places in the world to keep going back to the same one.
I believe that. I really do.
But here's the catch... sometimes going back is the better trip.
Let me explain.
No matter how great your trip planning is, or how much energy you have, you can never see everything a city has to offer. It's just not possible.
I live in Philly. I'm still learning new things about Philly. If I can't finish my own city, how am I supposed to finish Paris in five days?
I've written about how many days a city really needs. Even when you get that number right, you still leave things on the table.
For the big ones like Paris, London, and Rome, going back is a no-brainer. There's just too much.
Here's why a return trip pays off.
You finally get to the thing you missed
The obvious reason is time. Time for the sights and excursions that didn't make the cut the first time.
When I went to London this April, I made sure I saw Shakespeare's Globe. I missed it on my first trip years ago, and it was killing me. This time it went straight to the top of the list. No debate.

Me in 2016. Why am I wearing a jacket with a pocket square? Scroll below to see me 10 years later.
You get to eat more
Unless you're a competitive eater, there is no way you can hit every restaurant you want in one trip.
Your stomach has limits. Your trip has limits. The list doesn't.
Going back gives you a second round at the places you had to skip. And the first trip usually adds a few new ones to the list anyway.
You get to explore the side cities
The first trip is all about the main city. That makes sense. You want to see the famous stuff.
But a lot of great cities have smaller towns nearby that are easy to reach. On a return trip, you're not stressing about the big sights anymore. So you can take a day and get out of town.
Believe it or not, some of those less hyped places end up being the highlight. I made that case in my five year anniversary issue.
You see it with new eyes
Here's one I didn't expect. The city might be the same, but you're not.
On that same London trip, I went to the Tate Modern. Now that I know a little more about art, I actually appreciated what I was looking at. Same museum. Different experience.
The time between trips changes you. You read more, you learn more, you care about different things. A return trip lets you see a place through that newer version of yourself.
You finally get to relax
But here's the most important one for me. Peace of mind.
When I go back, I already know where everything is. I know how to get around. The main sights are out of the way. So I'm not rushing from one line to the next, trying to cram it all in.
I can slow down and just enjoy what the city has to offer.
Isn't that the whole point of traveling?

Me in April 2026
The cheat code
Here's a trick I love.
Think about where work is likely to send you. Maybe there's a conference city that comes up every year. Maybe there's an office your team visits a lot.
Go there first, on your own time.
Yes, you pay for that first trip. But you get to see the city your way, at your own pace, with the people you want to see it with.
Then when work sends you there, it becomes your relaxed second visit.
While your coworkers are busting their necks trying to squeeze in the sights between meetings, you already did that. You get to pick the one or two things you missed and actually enjoy them.
Want to stretch it? Ask to stay through the weekend. The flight's already covered. You'll pay for the extra hotel nights yourself, but that's a pretty cheap mini vacation. I shared more ways to get the most out of a work trip in this issue.
So yes, I love seeing new places. I always will.
But sometimes going back is even better.
Be honest. Are you a "new places only" traveler or a "go back to my favorites" traveler?












