Should you travel to new places or go back to old favorites?

I often say that the problems I have now are the best problems I’ve ever had.

One of these “problems” is deciding between traveling to new, exciting locales or going back to locations that I already know that I love. Even as a remote-working digital nomad, my travel time is limited and precious to me.

My dream, and one of the reasons I travel so much, is to see as much of the world as I can. Travel has given me a great amount of perspective and really shaped my worldview, and I think I will also want to visit new places.

But that said, having been to 49 countries and most states already, there are so many places that I’ve loved and want to revisit (in fact, as I write this, I am on a flight to Maui, having just stayed there – at the same exact hotel – 4 months ago).

As a remote worker, it’s almost always easier to go to a location that I’ve been before, especially if I stay at the same hotel/Airbnb – I already know that there’s reliable WiFi, where to go nearby for quick meals, and will sometimes already have friends in those locations. This is one reason that I keep going back to Medellín and Puerto Vallarta, where I already have work routines in place.

Also, when my friends ask me to travel, just given all the places that I’ve been, it’s often to locations that are old hat to me. When that happens, I’ll usually look past the fact that I’ve been somewhere because the experience of going places with friends is usually worth the repeat in travel.

And just because I’ve been somewhere doesn’t mean that I’ve experienced it all. The third time I was in Medellín, for example, I took a tour that took me to some stunning places 2-3 hours outside of the city. Sure, I didn’t get to mark off a new country, but that trip was unforgettable.

So, for me, it’s a delicate balance and I usually try to split my travel 50/50 between places I’ve been and places that I want to go. Of course, when I was newer to travel, I was purely focused on new places, which I think makes a lot of sense if you’re just getting started – it’s very hard to tell what you’d like and what you wouldn’t if you only have a small sample size.

Do you prefer going to places you’ve been or to new destinations? Let me know in the comments!