22 Fantastic Destinations for the Lifestyle Entrepreneur

By Sean Ogle •  Updated: 10/13/15 •  16 min read

Back when I was working at my day job, I used to go run around the Willamette River in Portland, Oregon almost every day on my lunch break.

Every time I’d pretend that I was running along the banks of a tropical beach, someplace faraway and exotic.

Once I left my job and moved to Thailand, that was one of the first memories I had – running down the beach in Ao Nang, Thailand living out that dream.

bamboo bars, ao nang, krabi, thailand

Soi of bamboo bars in Ao Nang, Krabi, Thailand

Since then I’ve worked from dozens of different places – and talked to hundreds of others that have as well.

That’s what’s so cool about this Location Rebel lifestyle thing – as long as you have wifi and a laptop you can pretty much go wherever you want.

But what are the best places to go?

If you’re looking to either make a permanent move, or perhaps take a month long “workcation” – how do you decide what the best decision is going to be for your goals.

After all, everyone has a different definition of paradise, right?

In today’s post we’re profiling 22 of the absolute best places in the world to go run your location independent business.

Unfortunately there’s no one size fits all dream spot – each is going to have it’s pros and cons, and the goal of this post is to help you make a decision on what’s right for you.

For some of you, you might stop at many of these places on an around-the-world adventure.

Others, of you may just be looking for a change of routine for a month or two.

And some of you might be looking for a new place to permanently settle down and enjoy your new entrepreneurial life.

Regardless of what you want, one of these destinations will probably have what you’re looking for.

I broke them down into three different categories:

From there I broke each city down into 6 different sections, to help give you a sense of what to expect based on your priorities in a location.

Keep in mind this is based on my opinion, so what I think is a 5 star food city may only be 3 stars for you… 🙂

It’s also worth noting different countries have different visa requirements, so you may only be able to do some of these on a short term basis (or not at all) if you’re sticking with a tourist visa



Portland, Oregon

HDR photo of Mt Hood and Portland Oregon

View from Vista Bridge

Portland is one of my favorite cities in the world, and that’s why I’ve chosen it as my home based when I’m not on the road. It’s easy to get around, has a phenomenal food scene that is affordable, and gives you easy access to just about any outdoor activity you could want.

Read more: Portland, Oregon is a Hub for Entrepreneurship

Austin, Texas

Austin is similar to Portland, but with more cowboy boots.

The food and booze is cheaper, there’s even more music, and the weather is quite a bit warmer. There’s also quickly growing startup scene there, but unfortunately housing costs are risking in kind.

Just do yourself a favor and stay away from the $5 “liquor pitchers” at Shakespeares…

Read more: Quick Guide to Austin’s Start Up Scene

San Diego, California

San Diego, California

San Diego – Image Credit

San Diego has become a hotbed of internet entrepreneurs. It seems like every time I meet someone new, when I ask where they’re from, the unsurprising answer is “San Diego.”

And what’s not to like, sunshine, beaches, opportunities to meet likeminded people? Sounds pretty perfect.

Read more: An (Incomplete) San Diego Entrepreneur Resource Guide

Bend, Oregon

Sunriver, Oregon

From the deck outside Bend, Oregon

Bend makes this list because it’s one of my favorite places on earth. You’ll be a little bit more secluded both in terms of ease of getting around and like-minded solopreneurs, but if you’re looking for a place to move where you can have unlimited outdoor activities, fantastic beer, and a slower pace of life – Bend is as good of an option as anything.

Read more: Bigger in Bend – Building a Regional Start Up Cluster

Vancouver, CA


Coal Harbor, Vancouver, BC – Image Credit

I keep hearing about how Vancouver is an up and coming entrepreneurial city and also has the scenery, infrastructure and culinary scene to make it a great place to live.

Downsides? It’s expensive

Read more: A Creative City Guide to Living and Working in Vancouver

Liverpool, England

Liverpool, England - Image Credit

Liverpool, England – Image Credit

Though London might be the first place to come to mind when you think of England, Liverpool is a lot more than just the home of the Beatles.

Not only is the north of England far more affordable, but Liverpool has a growing entrepreneurial scene, plenty of cafes to work in, zero language barriers, and is just a quick flight away from virtually anywhere in Europe when the weather gets bad.

Read more: Entrepreneurs Start Lining Up to Create Merseyside “Super Businesses”


Berlin, Germany

Berlin, Germany - Image Credit

Berlin, Germany – Image Credit

Berlin has become a spot that has many lifestyle entrepreneurs flocking, especially during the summer months. With lower costs than many other cities on the continent, and plenty of English speaking locals and ex-pats around.

What many love about Berlin is it’s become an exciting start up community, especially in creative fields like art, design, and fashion, that’s growing along with the popularity of the city.

Read more: Berlin: The Start Up City that’s Still Starting Up

Bangkok, Thailand

Cheap Charlies

One of the best bars in the world: Cheap Charlie’s in BKK.

This might be the first place most budding online entrepreneurs decide to head, and it’s pretty easy to see why. Bangkok can give you a full city lifestyle, great food, and tons of expats doing pretty amazing stuff, for a fraction of the cost.

It’s no surprise this is one of the prime starting spots for those who want to grow their business on the cheap.

It doesn’t hurt it’s one of my  favorite cities on Earth. If you go though, go for at least a week, otherwise, you’ll probably dismiss it as “just another big city.”

Read more: What’s it Like Being an Entrepreneur in Thailand

Chiang Mai, Thailand

Chiang Mail, Thailand - Image Credit

Chiang Mail, Thailand – Image Credit

One of the other big hubs of entrepreneur and ex-pat lifestyle in Asia has to be Chiang Mai. Pop into any of the bars, restaurants, or co-working spaces in the city and you’ll sure to be find someone with their laptop open hard at work.

This is one of the best destinations to head to when you’re bootstrapping and growing your business.

Read more: 5 Damn Good Reasons to Start Up in Chiang Mai

Bali, Indonesia

Bali Sunset

Sunset on Seminyak Beach

Bali is one of my favorite recommendations for people looking for an “exotic, yet accessible” Location Rebel destination.

I like to tell people it has everything Thailand has, but it’s all located on one relatively small island. Cost of living can be as cheap or as expensive as you want. It’s just as easy to find a fantastic $3 lunch as it is a $13 cocktail at a 5 star hotel.

Low key lifestyle, lots of travelers and entrepreneurs flowing through, and strong focus on a healthy lifestyle – especially up in Ubud.

Read more:

New York, New York

Panorama Image of NYC from the Gansevoort Hotel

The view from the Gansevoort on my first trip to NYC.

There’s a reason why New York is one of the best cities in the world. It has everything. A thriving network of entrepreneurs, tons of places to work from, some of the best food from all over the world, and different activities every single day of the week.

It’s not called the city that doesn’t sleep for a reason! The downside, it’s not cheap, but more and more people are expanding out to Queens and New Jersey to get the perks of the city, only a short subway ride away.

Read more: Why New York City is a Great Place to be an Entrepreneur

Manila, Philippines

Manila is an interesting place. It’s kind of a dirtier version of Los Angeles in my mind. The food is well, horrendous, but the people are extremely friendly – and most speak English, which can help make this a great spot for new Rebels looking to get some work done.

There’s a thriving entrepreneurial scene and access to cheap, high-quality workers. You’re also just a quick flight over to exotic hot spots like Boracay 🙂

Medellin, Colombia

Huge shoutout to LR members David, Mike, and Dave hanging down in Colombia.

Huge shoutout to LR members David, Mike, and Dave hanging out down in Colombia.

If you’re looking to try out the South American lifestyle, you’ll find quite a few people (including many Location Rebel members) telling you that Medellin is where it’s at.

With a thriving community of location independent types, a growing entrepreneurial spirit, great foot, and plenty of co-working spots, it’s easy to see why it’s growing in popularity.

Read more: Medellin Marvels with a Magnificent Entrepreneurial Culture

Barcelona, Spain

Barcelona, Spain

Barcelona, Spain – Image Credit

Many of the traveling lifestyle entrepreneurial crowd heads to Barcelona during the “smog” seasons that you’ll generally find in Southeast Asia.

With a vibrant community, lots of younger people, nice beaches, and not to mention amazing culture, Barcelona is attracting more and more people who are looking to grow their businesses online each year.

Read more: Why Entrepreneurs are Flocking to Spain this Summer

Hong Kong

View of Hong Kong from Victoria Peak

View of Hong Kong from Victoria Peak

Hong Kong has it all, a vibrant city, tons to do, fascinating culture, you name it. So, it’s no wonder it’s been at the very top of the lists of international cities for a long time.

A place like Hong Kong attracts the biggest and best players in the game, but that comes at a price, an expensive one at that. If you want to really up your skills and network with big time entrepreneurs, this is the place to do it.

It’s also a fantastic hub with easy access to other major Asian cities.

Read more: Hong Kong is Calling Entrepreneurs

Prague, Czech Republic

Prague, Czech Republic

Prague, Czech Republic – Image Credit

For the last few years, Prague has been seen as the hub for nomads and online entrepreneurs in Eastern Europe. With a heavy cafe culture, and plenty of English speaking locals and ex-pats, you’ll be able to jump right in.

One thing to keep in mind is if you are looking for a place with a party atmosphere, Prague is on the quieter end of the spectrum, which is great for getting work done.

Read more: Prague Start Up City Guide

Las Palmas, Spain

Las Palmas

Las Palmas – Image Credit

This little island off the coast of Morocco has found a new resurgence with a thriving entrepreneurial community who sees it as way more than a great surfing destination (though that’s a great feature too).

Not only is it becoming a hot spot for conferences, but there are a number of co-living spaces popping up all over the island that cater directly to bootstrappers who are looking fora  home base in Europe (plus the weather is pretty sweet too).

Read more: 10 Reasons Why Digital Nomads Should Visit Gran Canaria

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Rio de Janeiro, Brazil

You want a party? Beautiful beaches? The place that inspired me to start this blog in the first place?

Look no further than Rio de Janeiro, Brazil.

The cost of living is reasonable outside of the heavy tourist times (New Years, Carnival, Olympics), you’ve got plenty of outdoor activities and beaches to enjoy, plus there’s a growing community of digital nomads and expats always coming in and out of the city.

Downside is the city is riddled with crime, and as a gringo – you might as well be walking around with a bullseye on your chest.

Read more:

Saigon, Vietnam

Here is the "office" where I went back and edited this post. If there are spelling errors, you can see why I was probably distracted.

Ho Chi Minh City, or Saigon as the locals still call it, has one of the biggest lifestyle entreprenurship scenes in the world.

I was there earlier this year, and was reminded why Asia is such a good place to build a business.

If you’re staying near the touristy Bui Vien area – then this probably falls into the “intermediate” level, but if you get into other areas of town you could find yourself having a tough time getting around.

Not my favorite city to visit as a tourist, but a fantastic spot to live if you want to be around other expats doing cool stuff. Oh, and it’s remarkably inexpensive still.

Read more:

Guangzhou, China

Sunset in Guangzhou, China

Sunset in Guangzhou, China

Man, why would anyone want to live in Guangzhou, China of all places? For one? Because most other westerners don’t. What does this mean for you? Incredible opportunity, if you’re in the right business.

Looking to get into a product based business? With the Canton Fair and many of the biggest production factories in the world at your disposal, there’s arguably no better place to be.

This is China. Straight up. Better get cracking on your Mandarin. Life can be very cheap here, but if you want to be in one of the nicer areas of town, expect to pay higher prices.

Just make sure you trip doesn’t start out like this:

Read more: Is Guangzhou China’s Next Start Up Hub?

Santiago, Chile

Santiago, Chile

Santiago, Chile – Image Credit

Santiago has been a growing up for entrepreneurs and has a pretty exciting culture for start ups in South America. Because of that, more and more people who are looking to get into tech are heading south.

That being said, while the start up scene is great, if you are looking to do more freelancing or lifestyle type entrepreneurship, it might not be the best fit for a long term stay.

Read more: The Entrepreneurs Guide to Living and Traveling in Santiago

Lisbon, Portugal

Lisbon, Portugal

Lisbon, Portugal – Image Credit

It seems like Portugal has been long overshadowed by it’s other European cousins, but right now it’s one of the hottest spots for start up and entrepreneurial culture around. There has been a huge growth of incubators, accelerators, and start ups hitting Lisbon.

Couple that with a beautiful city, friendly locals, and lots to eat and drink, on a budget price for Europe, this place is poised to explode in the coming years.

Read more: Portugal Discovers it’s Spirit of Entrepreneurial Adventure

So any of these destinations click with you? Ready to hop on a plane?

Let us know in the comments where you want to go on your next big trip. Is it one of these? Or did we leave someplace out?

Additonal Image Credit: map

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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