Finding Better Destinations To Travel as Digital Nomad or Remote Worker
Why I Stopped Letting Lists Choose My Trips
So here’s the thing. I used to be that person—the one who’d Google “Top 10 Places to Visit This Year” or Instagram slides and then try to tick them off like a checklist. I once booked a trip to Santorini purely because it was plastered all over Pinterest with those dreamy white houses and blue domes. Yes, I did that too.
You know what happened? I spent more time queuing for sunset photo spots than actually experiencing anything. I felt like I was playing a part in someone else’s vacation.
That trip taught me something important: just because a place is popular doesn’t mean it’s the right destination for you. “Better” isn’t about checking off the biggest names—it’s about finding spots that actually fit your energy, your interests, and your weird travel quirks.
Be Led By Your Interests, Not the Algorithm
This is a lesson I learned in Oaxaca, Mexico. I’d been to Mexico before—Cancún, Playa del Carmen, the usual suspects—but Oaxaca was different. I went there solely because I wanted to try the mole (a rich, spicy sauce) in, like, 50 variations. Well, there were other reasons too, like the architecture and the fact that it’s one of the safest cities in Mexico.
I didn’t plan much. Just booked a guesthouse and followed my cravings. Ended up in mezcal tastings with locals, exploring indigenous markets, and watching traditional dances in the town square by accident one night.
That trip didn’t just satisfy my stomach—it completely shifted how I travel. Now I start by asking, what do I actually want to do or feel on this trip? Like, really. Do I want to wander old bookstores? Swim under waterfalls? Work in cafés with fast Wi-Fi?
One time, I was in Bansko for the Nomad Bansko Fest and then I chose to stay longer in this random city in Bulgaria because it had a jazz bar inside a cave (yes, an actual cave). I didn’t even know what else was there. But it was magical.
It’s also a personal pursuit, so you’ll want to think about some of the things that you are keen to do and allow your search to be led by those. This means you’ll end up in a spot that’s much better suited to you and your desires, which is a hugely important thing to be aware of. It’s amazing how much this can help, and you are going to be in a much better situation overall when you do find yourself traveling there, knowing that you are going to have so much fun there.
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Go Beyond the Top 10 Lists (Seriously, Please)
Discovering Kanazawa from a friend
Kanazawa is a hidden gem on Japan’s west coast, blending rich samurai history with modern charm. You should visit it for its beautifully preserved geisha and samurai districts, one of Japan’s top three landscape gardens (Kenrokuen), fresh seafood at Omicho Market, and a thriving arts scene—including gold leaf crafts and contemporary museums. It’s like Kyoto without the crowds.
Here’s my hot take: Most of the top 10 lists are written for clicks, not connection. It depends on the publisher, but usually that’s what you get, so be careful!
I get the appeal—they’re easy. You’re planning a trip, you’re busy, so you google “Top 10 places in Italy.” Boom, there’s your itinerary. But what those lists don’t tell you is that everyone else has read the same thing. You’re going to be elbowing people for a cappuccino in Florence while trying to enjoy the “authentic local charm.”
Now, my favorite trick is to go deep. I’ll search “[Country] best underrated towns” or join Facebook groups and ask actual locals where they’d take a friend for the weekend. Or another fantastic trick is to look for some subreddits like “/travelhacks” on Reddit for underrated destinations.
That’s how I ended up in Cuenca, Ecuador. No one mentioned it in any list, but it had cobbled streets, expat artists, and $2 lunches that put most big-city restaurants to shame.
Check Out Property Listings (Weird Trick That Works)
Okay, this might sound a little weird, but stay with me.
Sometimes when I’m exploring where to go next, I open up Airbnb or even local property rental sites—not because I’m ready to rent long-term, but to get a feel for what life looks like there.
If a city’s listings are all “Instagram dream lofts” and $300 a night, I know I’ll probably be surrounded by influencers and cocktail bars—not my vibe. But if I see cosy little places with basic kitchens, friendly reviews from digital nomads, and photos that look like someone’s grandma decorated the place? That’s my sign.
I once found this sleepy town in southern Spain where rentals were under $400 a month. I walked into a bakery the first morning and had an empanada with local goat cheese that made me rethink everything I thought I knew about pastries. I ended up staying two months.
So yeah—property listings = underrated travel research tool. Try it for fun. It might take some time, but you might find some hidden gems in there.
Consider Timing Over Hype
Timing is everything, and I learned that the hard way.
I went to Kyoto during cherry blossom season, thinking I’d have this peaceful, poetic experience. You know—blooming trees, quiet temples, maybe a cup of matcha while journaling. What I got instead was a sea of selfie sticks and about a thousand people trying to get the exact same photo on the Philosopher’s Path.
The thing is, the magic of a place isn’t always about the season everyone talks about. Sometimes it’s better right before or right after. I went back to Japan in November once—no blossoms, no crowds, just autumn leaves, crisp air, and the quiet I’d originally hoped for.
Same goes for beach towns: I once visited a Greek island in late September, and everything was still open, the sea was warm, but the crowds were gone. Locals had time to chat again. It felt like I had the whole place to myself. Greece is definitely something to put on your map for September and even October. Less busy, cheaper, quieter.
So yeah, don’t just ask where to go—ask when. It might make all the difference
Final Thoughts: You Don’t Need the World’s Approval to Go Somewhere Cool
Travel’s not a popularity contest. The best destinations I’ve ever found were the ones that matched me—not the ones I saw trending, not the ones on “Top 10” videos, and not the ones I picked because I thought people would be impressed.
Find your weird little corners of the world. Follow a hunch. Go where the food looks good and the people look like they’d invite you in for coffee.
And if you ever find a jazz bar in a cave again—let me know. I’m always down.
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Travel Insurance
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Accommodations
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Recommended places for long-term stay
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