It’s natural to wonder what it would be like to live on a rock. Perhaps you’ve found yourself on vacation on a beautiful island and are thinking, “Imagine what it would be like to live here!”

It happened to me too. I pondered that very thought myself, and I eventually made the move.

People often ask me how I chose which particular island to live on, so I thought I’d share some of the things I considered in my decision-making process that might just help you too.

Here are 9 questions to consider when choosing the right island for you:


1. How important is safety/infrastructure to you?

Safety is a relative term. There are places on every corner of Earth that you’re advised not to go to. Still, it’s important for me to generally feel safe in most places on my rock.

Infrastructure is also something to consider. I want a rock that has decent roads. Doesn’t everyone?  But see, I come from Louisiana where the running joke is: “Potholes are deeper than my pockets!” I tell myself, “If I can’t find a rock with decent roads, I’ll buy a Jeep. The problem won’t be entirely solved, but at least I’ll have more fun!” At least that’s what I keep telling myself. A little naïve, I have to admit. Really though, infrastructure goes way deeper than road quality. Check into it. Islands with less infrastructure can be less expensive to live on and I’ve been told it can certainly add to the island’s charm.


2. How easy is it to access adequate healthcare? If “shit hits the fan,” where are you going to go?

 I had this conversation with my dad several years ago when he told me the story of a friend who was in Puerto Rico. His friend was walking on a beach and stepped on a steak knife that was poking out of the sand. His friend was taken to the local Puerto Rican hospital. Dad said, “Well, if it was my foot on the line, I’d be flying to Miami.” The Puerto Rican surgeon said, “You know, he’s right. That’s your best option.” Although a scary story, I am hopeful that the healthcare on Puerto Rico has since improved.

Even if you don’t currently need medical facilities, having adequate ones nearby just in case may give you peace of mind. I know it does for me.


moving to an island choosing an island


3. Distance from home. If there’s a family crisis, how hard will it be to get back home in a pinch?

Are you OK with spending $1,000+ on airfare in the event of a family emergency back home? I really don’t want to spend that much (obviously), but I keep an emergency fund just in case. Look at the amount of flights that go out of each island’s airport to your preferred airport back home. If from my rock, I can only fly home on a Wednesday or a Saturday, and there’s only one flight home on these days, that will definitely be a factor in whether I decide to move to that rock or not. Some islands like the Bahamas, the Florida Keys, and a few other Caribbean islands are fairly easy to get to if you’re coming from the US. If a more remote locale is what you desire, just know it will not be as easy to get home (I realize that for some people, this may be a benefit).


4. How easy is it to get a job?

Are there jobs that relate to your career or interests? On many islands, tourism is a huge source of revenue. Can you work in that field? Could you keep your current job and work remotely? Could you realistically start your own business on the island you’re interested in?

Some people like to find jobs ahead of moving to their rock, others like to move then figure out the job situation. Which do you prefer? Every rock’s job market works differently. On some islands, it is easier to find a job and do most of the paperwork remotely. On other rocks, all of the paperwork must be done in person when you arrive. Unless you’re independently wealthy, this is an important one to research.


5. Cost of living vs. wages – can you realistically make it work?

When I first dreamed of living and working in Hawaii, I said I’d take any job and make it work. Well, when you realize you’re going to get paid barely enough to cover rent, much less food, reality sets in. Because I wanted to make it work so badly though, I became irrational very quickly. Car? Nah, I don’t need that. Food? I’ll eat peanut butter sandwiches for life. Activities? Aren’t those supposed to be free?

Some places, your money stretches far. Other places, not so much. What is the currency conversion rate and in what currency will you be paid in for work? Look online at properties to rent on your island. On average, how much per month will a house or home that fits most of your requirements cost? What is the average pay of the job you want on the island you’re looking at?


6. Is needing a specific passport or having to get a visa going to be a problem for you?

Fresh out of college, I know for a fact I don’t want to deal with visas. This is why I’m sticking to US islands and territories for now. When I’m feeling more adventurous, I imagine I’ll have no problems with getting a visa. In some locations, getting a visa is easy. In others, it can be a nightmare! Know before you go.


moving to an island choosing how to


7. Is getting frequent rock fever a concern of yours? Size does matter.

I’m talking about how terrain affects your perception of size. To me, if an island has hills and mountains, it feels like a large island even if it isn’t. For me, more hills means less island fever. You may not even get island fever, or it may be months or years until you get it. But knowing yourself and your propensity towards feeling stuck in small places will be useful in choosing an island.


 8. What culture are you looking for? Is a large expatriate community something that’s important to you?

 I’ve always been interested in Polynesian culture, so it makes sense for me to move to an island where I can delve into it. Researching the culture and the general community vibe before you make the leap will likely help you to feel more at home and connected once you move.


9. What are your favorite activities?

Besides the professional sport of island drinking, what other activities do you like to do? I want to surf, snorkel, boogie board (no, it’s not just for kiddos thank you very much) and paddle board. Some islands have relatively flat water that’s not great for surfing. Other islands have somewhat flat terrain where hiking is not an option. I want waves, calm water, and mountains. This is a tall order!

Some islands have fantastic communities for those interested in yoga, others are known for sailing. Some islands have a little bit of everything – while others have very few extracurricular activities available. While you may find a new favorite activity once you move, keeping your natural interests in mind can help you feel happier in your island life overall.


Final Thoughts:

Do yourself a favor and make a spreadsheet. At the very least, make a paper list. And make several copies. If you’re super organized, make an Excel spreadsheet of every island you think you want to move to. Regardless of your note-taking methods, you’ll need to do your research and make columns for pros and cons of each island you’re considering. Input all of your research into a literal or computer file folder. You’ll be surprised how fast the islands and the pros and cons melt together. A week from now you won’t remember whether rent was cheaper on Grand Cayman or St. Croix. You certainly won’t remember each pro and con a month from now.

Every moving blog or article states the same thing: visit your desired island before deciding to move there. I think we’ve all read at least some of the blog posts on the internet regarding the joys of rock life, but also the regrets, fears, and other frustrations of living on a rock. Maybe you underestimated the cost of living, thought a lack of solid infrastructure was what you wanted, or you couldn’t deal with rock fever. Whatever the issue is, many people state that a short-term visit to any rock you’re thinking of moving to is a worthwhile investment.

In my opinion, worst case scenario: you got a great vacation out of your visit. Best case scenario: you decided you really did want to move there!

Most importantly, don’t talk yourself out of moving to a rock because of fear of the unknown. Only you know what you’re capable of. If you say it’s your dream to move to a rock, do it! Do your research, but don’t stress yourself out. Enjoy the process and imagine what you have to look forward to. Yes, moving to a rock will have its stressful moments, but see it as an adventure. This is what YOU want to do. Now, go for it!


How to choose an island to move to


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What questions did you consider before choosing the rock you reside on?

Written By:

Current Rock of Residence:

Perdido Key

Island Girl Since:


Originally Hails From:

South Louisiana

A water baby since toddlerhood, Olivia was in the water any chance she got. Waves, pools, sprinklers – it didn’t matter. This girl is willing to swim in any body of water deemed safe (or not), and the only person crazy enough to swim in the ocean without a wetsuit in the middle of March. She moved to the beach and became a “professional” boogie boarder, margarita tester, beach runner, and roach killer. She loves boating, traveling to any new beach, and enjoys trying (and failing) at new water sports.

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