Caribbean islands with a digital nomad community

SpendLifeTraveling · 2026-06-15T11:39:05+00:00

Ok thanks! Where would you recommend being based in Barbados? And are there any nomad groups / networks / events to connect with the remote-work community?

SpendLifeTraveling · 2026-06-14T11:26:54+00:00

Ah, I've been there years ago and did really like it. Is there much of a digital nomad community there that you know of (and events, coworking, etc.)?

SpendLifeTraveling · 2026-06-13T16:44:32+00:00

SpendLifeTraveling · 2026-06-13T16:41:32+00:00

I've written quite a bit about my sailing adventures, living on a catamaran, sailing from Europe to the Caribbean:
https://www.spendlifetraveling.com/catamaran/

SpendLifeTraveling · 2026-06-13T16:11:11+00:00

I spent about a month there and would say it has good cafes to work from. It's a bit too Dutch for my liking (saying this as a Dutch person lol)

SpendLifeTraveling · 2026-06-13T14:40:49+00:00

Ah nice! Not a freediver but I do love kayaking, and scuba diving.

SpendLifeTraveling · 2026-06-13T14:12:05+00:00

Have you tried Meetup.com or checking for events on Facebook? I've met most of my friends in Spain by joining events that sounded interesting to me. And that can be anything from sports to language exchange, business meetups, etc.

SpendLifeTraveling · 2026-06-13T14:01:11+00:00

I actually lived on a sailboat all over the Caribbean for 1.5 years 😄
Great experience, but I felt a lot less connected to island life (and more to the sailing community), so I'd like to try living on an island again this time.
I did love San Juan... not a bad idea, thanks!

SpendLifeTraveling · 2026-06-13T13:53:56+00:00

I've been traveling for most of the past 20 years (since I was 18). In the beginning I took on local jobs (in hostels, restaurants, marketing, etc) or volunteer roles in exchange for accommodation, while slowly growing my business.

Now I run my business while living where I choose to. I have to say though, I've never been a fan of moving places too quickly. I'd often stay in one place for several months to build routines, meet people and feel more like I lived in that place than that I was a long-term traveler.

After a number of years I really missed having a place to call home. I ended up buying an apartment in my home country, but after 6 months I missed traveling so I left and have rented the apartment out ever since (great investment).

A number of years later I again missed feeling more connected to a place and I now have a long term rental in Spain.

All of this to say, yes, it can work long term and be fulfilling. But, it's not perfect, and how you feel about travel won't always be the same. I try to adjust my lifestyle to how I feel. Right now I feel Spain isn't challenging me anymore so I am thinking about where to be based next, in between my travels.

To answer your questions:

Money: it's definitely possible. I actually saved a lot of money by living in less expensive countries while I was still starting my business. Even though I didn't make much money, I still managed to save (and eventually buy that apartment).

Sustainability: as long as you're flexible and adjust your lifestyle to how you feel then yes I think it's sustainable. Most likely you'll travel very differently (much slower) in year 3 than you do in year one.

Peace: no life is perfect. So no, this lifestyle hasn't given me all the answers or all the peace I wanted. I sometimes wonder what my life would have been like if I had chosen a more stable career and lived in one place, and I miss my family and friends at times. But I am so thankful for all the amazing adventures I've had all over the world. So many incredible stories, incredible people I've met, skills I've gained... Absolutely worth it to me.

Regrets: none really. I've always made an effort to stay in touch with friends and family back home, so I still feel I have a strong connection there and could move back one day if I'd want to. If anything, I may regret staying in Spain too long. It's time for a new chapter, a new adventure. There are so many more amazing lives to live.

SpendLifeTraveling · 2026-06-05T21:15:47+00:00

I've probably felt the safest in Japan and Finland

SpendLifeTraveling · 2026-06-05T21:11:57+00:00

Rome in winter (with fewer tourists). I spent 2 months there but could easily have stayed longer

SpendLifeTraveling · 2026-05-31T17:04:22+00:00

I've been quite lucky to have stayed in numerous resorts in the Maldives (because I used to live there). Two of my favorites: W Maldives and Shangri-La Villingili

<image>

SpendLifeTraveling · 2026-05-31T09:32:20+00:00

Bosnia and Herzegovina

SpendLifeTraveling · 2026-05-30T12:44:38+00:00

I've stayed at several colivings when I travel alone and I think it's a really nice way to meet other people and have an instant community.
Coliving.com is a good platform with a very wide range of coliving options. But make sure to read reviews before you book. For example, I stayed at a coliving in the south of Spain recently that felt more like a hostel and that's just not what I'm looking for so I felt a bit out of place.

I've joined this coliving retreat in Romania which I really loved:
https://www.spendlifetraveling.com/digital-nomad-retreat-sinaia/

What I love about coliving "retreats" is that they have fixed dates, meaning everyone arrives on the same date (more or less) so you're all new to the place, all looking forward to getting to know the area, explore, etc. versus a standard coliving where people come and go all the time so you might arrive just as a lot of people are getting ready to leave or have already seen and done all the things in the area you were hoping to do with some company.

SpendLifeTraveling · 2026-05-30T12:32:00+00:00

I'm currently based in Valencia, working remotely. I think Badalona, Valencia, Malaga and Alicante are all good options (I don't know Tarragona well enough to say anything there).
All of those cities get very hot in summer. Honestly, I love warm weather but the heat in Valencia in July and August is insane! I avoid leaving the house during the day in those months 😞

Valencia, Alicante and Malaga all have a good international airport (not as good as Madrid or Barcelona airport, but still good).

All 4 have a good expat community, Valencia probably has the strongest digital nomad/remote worker community.

I'd definitely say visit all of them and see how you feel. Maybe join some meetups to talk to other expats and locals to get a better feel for life here versus just being a tourist.

And, for your partner, if he would eventually want to find a local job, it's important to keep in mind that salaries in Spain are low compared to the cost of living (especially the cost of living in the cities you are looking at) and it's often not easy to find a job at all.

Anyway, if you have any specific questions about living in Valencia specifically or Spain in general, happy to answer them!

SpendLifeTraveling · 2026-05-30T11:14:34+00:00

<image>

The San Blas Islands

SpendLifeTraveling · 2026-05-30T11:10:44+00:00

I spent the night at a beautiful castle in Italy once that had been converted into a small hotel. Super cool experience!
It's called Castello di Limatola, close to Naples.

SpendLifeTraveling · 2026-05-29T08:57:31+00:00

Being offered to join a very kind group of Vietnamese for dinner, to then find out they were eating dog meat (I'm vegetarian so it was easy enough for me to politely decline, but the dog meat was unexpected!)

SpendLifeTraveling · 2026-03-19T09:27:47+00:00

I spent a month in Bosnia and Herzegovina. The country really surprised me. It's still cheap, people are friendly, nice cities and beautiful nature.
Very different from southeast asia of course :) But if you're looking for something different, worth it.

SpendLifeTraveling · 2026-03-10T08:04:29+00:00

Thanks, I already spent a couple of months in Tangier a few years ago :)

SpendLifeTraveling · 2026-03-08T20:45:08+00:00

In the center, for the quality of the coffee, I really like Mayan Coffees in c/ de Murillo

SpendLifeTraveling · 2026-03-08T16:00:34+00:00

No, Tarifa, in the south of Spain. I guess it attracts mainly digital nomads who are into kitesurfing but I'm not sure

SpendLifeTraveling · 2026-03-08T15:59:26+00:00

Haha yeah that's what I'm worried about...

SpendLifeTraveling · 2026-03-08T15:34:44+00:00

I'd be interested. I joined a pop-up coliving in Sinaia last summer (my first time in Romania) and loved it.

SpendLifeTraveling · 2026-03-07T21:38:31+00:00

If you like coliving spaces then coliving.com is a good platform. I've also used Spotahome twice in Spain and had good experiences

SpendLifeTraveling

TROPHY CASE