Top 10 Places to Travel to in the World for the Woman Who Overthinks Every Move

You have had the tabs open for weeks. Maybe months. A shortlist that keeps growing instead of shrinking, because every place you add makes the decision harder, not easier. You are not stuck on whether to go. You are stuck on where, and the stuck-ness has quietly become the point.

Here is my honest read on the top 10 places to travel to in the world when you are already building a freedom business and it hasn't paid off yet: the list matters far less than picking one and going. A change of scene doesn't fix a broken business, but it does break the loop of staring at the same walls and calling it strategy.

I have lived in more than 60 countries since I left Australia in January 2016 "deliberately homeless." I did not get there by researching the perfect first stop. I got there by choosing badly, often, and moving anyway.

What are the top 10 places to travel to in the world when you're building a business?

The top 10 places to travel to in the world, for a founder who needs cheap rent, decent wifi and a nervous system that finally settles, are: Fethiye (Turkey), Bansko (Bulgaria), Chiang Mai (Thailand), Medellín (Colombia), Playa del Carmen (Mexico), Lisbon (Portugal), Tbilisi (Georgia), Canggu (Bali), Split (Croatia), and Da Nang (Vietnam). Each one is affordable, welcoming to remote workers, and forgiving of a business that isn't fully profitable yet.

Notice what these have in common. None of them are the flashy, once-in-a-lifetime bucket-list stops. They are places you can land, breathe, work, and afford. That is a different list than the one Google usually hands you, because you are a different traveller than the one it assumes.

Why your travel shortlist keeps growing instead of shrinking

I know exactly why you can't pick. You are treating this like a permanent decision when it is a reversible one.

You can leave. That is the whole point of the life you are building. If Lisbon disappoints, you fly to Split. If the wifi in Bali is a joke that week, you move to a café or a different island. The stakes you have invented in your head are not real stakes.

I was diagnosed with ADHD in 2023, and one of the truest things I have ever said about myself is that I "did the right things in the wrong order." I overthought plenty. But I also learned that motion beats analysis nearly every time. The decision doesn't get clearer from the couch. It gets clearer from the airport.

If your inability to choose a country is really an inability to choose anything, that is worth naming. I wrote more about that pattern in how to pick one thing when you're stuck doing everything, because the same overwhelm that keeps you checking flight prices over and over is usually the thing keeping your business from earning.

The top 10 places to travel to in the world - and who each one suits

Here is the shortlist, with the honest reason each one earns its spot. Pick the first one that makes something in your chest go "yes" and stop reading the others.

1. Fethiye, Turkey

I rented an apartment here for $250 a month. Warm sea, warm people, and a cost of living that takes the financial pressure off while you sort out your income. If money is tight, start here.

2. Bansko, Bulgaria

A ski town with a serious founder community and a co-working culture in the off-season. We skied here. It's cheap, it's cold, and the people you meet are actually building things.

3. Chiang Mai, Thailand

The original remote-work base for a reason. Cheap, easy, endless cafés, and a soft landing if this is your first long stint abroad.

4. Medellín, Colombia

Spring weather all year, a low cost of living, and a city that hums. My Spanish came back to me fast in places like this - I learned it as a 17-year-old exchange student in Bolivia with four sentences to my name, and Latin America still feels like home.

5. Playa del Carmen, Mexico

We are moving to Mexico next, so I have skin in this one. Caribbean coast, good infrastructure, easy visas for many nationalities. It suits the founder who wants beach and function.

6. Lisbon, Portugal

More expensive than the others, but a proper hub for online business owners. If you want a peer group and don't mind paying for it, this is your stop.

7. Tbilisi, Georgia

A generous visa policy, absurdly good value, and a food-and-wine culture that will slow you down in the best way. Underrated and worth it.

8. Canggu, Bali

Loud, busy, and full of people selling courses about how to sell courses. But the mornings are beautiful and the community is real if you find the right corner of it.

9. Split, Croatia

Old-town charm, island-hopping on your doorstep, and a digital nomad visa that makes staying legal easy. Best in shoulder season.

10. Da Nang, Vietnam

Fast wifi, a long beach, and a cost of living that gives you room to breathe while your revenue catches up. Quiet, and I mean that as a compliment.

If you want the version of this list sorted by which base actually supports your workflow, I went deeper in the best places in the world to travel when you're building a business on the road.

How do you actually choose one and book it?

Set a timer for ten minutes. Look at the ten. Cross off anything that feels like a "should" rather than a pull. You will be down to three fast.

From those three, pick on one criterion only: money, weather, or wifi. Whichever one is causing you the most stress right now. If it's money, Fethiye or Da Nang. If it's the cold grinding you down, Medellín or Playa del Carmen. If it's your business needing rock-solid connection, Lisbon or Split.

Then book a flight that is refundable or cheap enough not to matter, and a week of accommodation. Not three months. A week. You are testing, not marrying.

The number of digital nomads has grown sharply, with an estimated 18.1 million American workers describing themselves as digital nomads in 2024. You are not doing anything strange or reckless. You are joining a very large group of people who figured out the same thing you have.

Will a new place actually fix the stuck feeling?

Partly. And I need to be straight with you, because this is where a lot of women lose a year.

A new place resets your energy, your attention, and your sense of what is possible. That is real and it matters. When I was drowning in my cake business, working 70 to 80 hour weeks while copycats undercut me, the problem was never my postcode. It was the business model. Moving cities wouldn't have saved me. Rebuilding the thing did.

So travel, absolutely. But don't expect Bali to do the work your offer, your pricing, or your focus needs to do. I wrote about this exact trap in why the laptop lifestyle isn't the problem - your stuck business is, and it's the most important thing I can tell you here.

The move and the fix are two separate jobs. Do both. Just don't confuse one for the other. If you want the full grown-up version of doing this without wrecking what you've built, start with travelling the world without blowing up the business you built.

What a change of scene is genuinely good for

It is good for shaking loose the story you've been telling yourself. When I flew out of Bolivia reading The 4-Hour Work Week, one question stopped me cold: if money were no object, what would you do? I could only write two words - travel, help people - and I realised I had lost myself.

New surroundings do that. They interrupt the autopilot long enough for you to hear yourself think. My daughter Sienna was running a boutique hotel's front of house at 10 because we kept saying yes to new places and new tries. Novelty isn't a distraction from the work. Sometimes it's the thing that makes the work make sense again.

Just go in knowing which job you're asking the trip to do. Reset your head - yes. Replace the business decisions you've been avoiding - no.

Frequently Asked Questions

What are the top 10 places to travel to in the world for remote work?

Fethiye, Bansko, Chiang Mai, Medellín, Playa del Carmen, Lisbon, Tbilisi, Canggu, Split and Da Nang. They balance affordability, good internet and a welcoming community for people running a business on the road.

Which of these is cheapest if my income isn't where I want it yet?

Fethiye, Da Nang and Chiang Mai are the gentlest on a tight budget. I paid $250 a month for an apartment in Fethiye, which took the money pressure off while I built.

How long should I book for my first stop?

One week. Test the place before you commit to a month or more. You are choosing a base, not signing a lease on the rest of your life.

Will travelling fix my stuck business?

No, and it's important to hear that. Travel resets your energy and attention, but your offer, pricing and focus are separate work. Do both, and don't confuse one for the other.

Do I need a special visa to work while I travel?

Several of these places now offer digital nomad visas, including Croatia and Portugal, while others like Georgia and Turkey are easy on long stays for many nationalities. Always check the current rules for your passport before booking.

You already know you can build a freedom life from anywhere. What you need now is to stop researching and start moving - on the trip and on the business. If the deeper reason you can't pick a country is that something in the business itself isn't working, be honest about that and go find it, starting with The Reality Check. Then book the week away, because the version of you who solves this is already on the plane.