Every place I’ve picked to live solo overseas for a month has ended up feeling like home. I’d love to credit my gut. But my gut also thought the Indianapolis Colts were going to the playoffs this year sooo…
You take a gamble anytime you book a place site unseen. But it can be especially scary when that place is overseas, and you’re there for any extended amount of time. You fear booking a misleading listing and ending up in a sketchy area that’s super far away from the best parts of a city.
Or you can do it the way I do it and eliminate that unnecessary stress.
I’m here to tell you that most of those fears about booking a shithole can be checked before you ever hit Book. By the end of this post, you’ll know how I tell whether a place will feel like home for 30 days. Before I book, not after.
Why you can trust my track record
As an 8x solo traveler who’s visited 15 countries and 44 states, plus extended stays in Portugal, Panama, Costa Rica, and Spain, I’m no stranger to Airbnb. It’s my preferred way to book lodging because most places feel home-like, and the hosts are some of the best resources for a destination's hidden gems. I have yet to have a bad experience (keyword: yet), so I feel pretty confident sharing my tricks of the trade!
Why getting it wrong costs you more than money
Picking the wrong extended stay location can wreak havoc on your solo trip and make you second-guess whether you’re actually cut out for this. You are. But your brain will try to play evil tricks on you and try to tell you you’re not.
A poorly researched lodging choice will not only cost you money, but it will also slow your momentum, make you question your safety, and sometimes shake your nerve to try again.
A bad weekend can sometimes make for a funny story. A bad month makes you wonder if you’ve made a horrible mistake and tears down your confidence.
Reimagining what your life could look like
Imagine walking into a coffee shop, and the barista knows your coffee order. Or walking around without having to use Google Maps. Or walking into a local restaurant and the bartender knows your drink order (this legit happened to me in Porto!). It’s like an international episode of Cheers.
There’s no reason that you can’t go from walking into a brand new city where you’ve never been to saying “I’m not from here, but I know my way around.”
That kind of big travel energy could get you to rule the world, girl.
That’s what you’re actually shopping for. Not a pretty apartment. A life you can slip into.
But fair warning: Good luck leaving.
Want a crew of women working up the nerve to solo travel too? The Solo Travel Sisterhood is free. Come as you are, leave ready to go. ✈️
The month that worked (and the one I almost booked)
When visiting Porto (a city which I consider myself in a long-distance relationship with), I’ve stayed in the Santa Catarina area near the famous Church of Saint Ildefonso twice now. I’ve fallen in love with this neighborhood, now know it like the back of my hand, and will probably continue to stay here during my future trips to Porto. And it wasn’t by accident.
The moment I knew this area worked for me was when I was wandering the streets and stumbling across a gorgeous tulip-filled park, visiting a funky brunch spot with colored coffees, and it was a quick 10-minute walk to Porto city center. It was heaven.
When I returned in 2026, I almost stayed in another Airbnb that was nearby. It was a really cute apartment and had all of the amenities I needed.
However, when I researched the location further, I discovered it was actually located in Porto’s red-light district. Not exactly the place I want to be.
I haven’t gotten it wrong yet. Notice I said yet.
The five factors that help me avoid big solo travel lodging f*ckups
My success rate isn’t luck. It’s only five questions.
For every place I’ve booked, both internationally and domestically, I run every place through the same five factors before I book anything.
Spoiler: #5 sounds obvious. And almost nobody does it the way I do.
Below the line: the five factors I check before I book a month anywhere.
