What If “Living Like a Local” Means Staying Put?

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Good morning ☀️ from Booked It On Points: A curated collection of travel tips and personal stories by me, Allie→ because you’re meant to experience meaningful travel no matter life’s constraints 👊🏽

Let’s dive in.

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✈︎ Travel Story

🌍 The Art of Staying Put

Just the other day, I came across this sarcastic article about “living like a local.”

The author’s take? Everywhere you go, locals don’t actually want to be there. Californians dream of New York. New Yorkers long for LA. Athenians fantasize about Berlin. Berliners crave Barcelona.

The ultimate way to “live like a local,” they joked, is to perfect the art of dissatisfaction, wanting to be anywhere but where you actually are.

Now I don’t know if I fully agree with the author’s take, I think there are people who love where they live, but it’s not the majority most likey. And I’m here to say that after four weeks in Syros, it feels… different.

🏝️ A Different Kind of Contentment

This little island in the Cyclades doesn’t seem to produce restless locals or itinerant dreamers. People here seem genuinely happy. There’s an ease, a groundedness, a pace that makes you exhale. The locals seem to know how good they have it. There isn’t a pressure of consumerism, quite the opposite. If you’re climbing an island of stairs to reach your front door, you better believe you aren’t hauling more than you need home.

As many here know, our kids are attending Boundless Life, the worldschooling program we joined when we left our traditional life behind. There are eight locations around the world, and most families hop from one to the next, between Portugal, Greece, Spain, Italy, Bali, Uruguay and soon to be Japan. It’s an incredible setup and fits our lifestyle perfectly!

But here in Syros, we’ve met several Boundless families who, well… never left. They came for a few months and decided to stay.

At some point, they looked around and thought:
“Why leave?”

🍷 The Simple Pleasures

The Aegean is impossibly blue.
The food is fresh and cheap.
The wine is… fine. (Let’s be honest, we’ve had better.)

But the gelato, oh man, the gelato, that’s legit.

Django Gelato has this wild story: they make everything using just fruit, sugar, and eggs. That’s it. You can read more about it here, but the real proof? Geo will happily spend 12 euros a few nights a week on dessert. And if you know Geo, you know that is wild!

✨ Stay or Go?

Who knows—maybe after three months we’ll get itchy feet again. Or maybe we’ll end up like those so-called “failed” Boundless families, perfectly happy to stay stuck here, in community, living simply and not over-thinking the big “life plan”.

What would you do, keep chasing the next place, or let yourself settle in?

✈︎ Travel Links

• Have you seen Geo run 100 miles? Bonus: he goes through 50 personalized travel tips along the way!

• Did you know? Breeze airline is offering 99$ NS flights to Cancun from Norfolk, Providence, Charleston and New Orleans !

• There’s a new “Camino” to check out, and it’s much cooler! (temps wise;)

• Prescribing travel for wellness, now there’s a prescription treatment- I can get behind!

• “Choose the bigger life!”- for me, it’s travel.

A lot for me to continue to think about this week- as usual! I hope you find yourself intentional in your lifestyle as well. Until next time, safe travels!

Allie & Geo