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How To Move To A Caribbean Island

I learned the happy news today that island friends of ours are moving back to St. Croix.  Like my husband and I, they tried to move back to the U.S. mainland after experiencing island life and have decided to make a u-turn from Tennessee.  Our quick turnaround was from Kansas (what were we thinking?!).

Yesterday I was playing with my young children at Tamarind Reef beach, when they met new buddies with which to look for hermit crabs.  The other boys and their parents were visiting St. Croix from New Jersey.  They were especially interesting to chat with, as they lived for more than a decade in Hawaii, where their oldest son was born.  Like us, they felt a tug to abandon island life in favor of being near family with their young kids.  But you could tell the island lifestyle remained fitting for them, as they were thoroughly enjoying their visit, and had many questions for me about life for young families on St. Croix.

I was recently inspired by a photo on the Women Who Live on Rocks Facebook page.  The image is of an Island Company cocktail tumbler which simply reads:

  • Quit your job
  • Buy a ticket
  • Get a tan
  • Fall in love
  • Never return

I share these stories together to echo one point … island life is incredible.  Once you experience it, you will be hard-pressed to feel that you’re living life to the fullest anywhere else.  So if you’ve ever felt the inkling to ditch a mainstream, cookie-cutter lifestyle … don’t hesitate!

That’s exactly what my husband and I did seven years ago.  After having a destination wedding on St. Croix in spring 2009, then finding out his job was changing to him travelling five days of every week, we decided to wait out the end of our apartment lease and take the plunge later that year.  Our plan was fairly simple … float on savings, try to wait tables or work retail, then return to the “real world” within two years.  What we found on-arrival was a welcoming community of people more than willing to help us find jobs, housing and vehicles.  We shortly found jobs in our respective career fields and the rest is history.

A few keys we discovered about making the leap to island life:

Have a one-way ticket to be taken seriously

In the digital age, so many people want to research and plan their transition to island life beforehand.  They hope to show up with full-time jobs secured, lease signed, vehicle lined-up, etc.  But that’s generally not the way it works here.  While The Farchette & Hanley Team site is extremely helpful to find a rental property online, they do recommend you be present on-island to see the places you’ll potentially rent in-person.  Once you’ve made a few trips, you’ll have a much better idea of which area(s) of St. Croix will best suit you.

Be flexible about income

In terms of jobs on-island, many are not listed anywhere official, but spread by word-of-mouth.  People around St. Croix are so helpful to newcomers in finding jobs, but you have to be here first (we’re jaded by so many tourists claiming they’re going to move, then never following through).  Try to be flexible, patient and think outside-the-box of a standard 8 to 5.  Be willing to be underemployed (at least temporarily), take multiple part-time jobs or work remotely for a company based off-island.

Be sure to check out the company and job listings with the U.S. Virgin Islands Economic Development Authority.  Thanks to the VIEDA, many companies you wouldn’t expect to find in the Caribbean are headquartered on St. Croix, St. Thomas and St. John because of substantial tax incentives.  If you own a business or have ambitions of starting one, this is a great resource of information.

Shed your stuff

For the most part, islanders are minimalists.  When you live in tropical paradise, there’s no need for fancy toys.  The climate here is also not friendly to many nice materials.  As most homes are open-air with humid / salty air blowing in, you should expect to contend with mold and rust.  Now there are certainly exceptions to this rule!  The Farchette & Hanley Team has some gorgeous, high-end home listings that have central air-conditioning and keep these environmental factors at bay (check out their featured home listings).

So consider having a massive yard sale, start selling on Craig’s List / eBay or just donate things to charity.  Pare down to the things that really matter to you.  My husband and I brought only what fit in suitcases we could check free with our airline status, plus what would fit in the SUV we shipped.  (Side note: Don’t try to ship anything inside a vehicle you ship to island.  This process is unfortunately notorious for things getting stolen.).

If you’re a pack rat or moving with kids, there are certainly shipping options.  Pallets are a good way to go, but you can fill entire shipping containers to put on the slow boat from Florida if need-be.  For smaller items, flat rate boxes from the U.S. Postal Service are the best friend of Virgin Islanders.  USPS is significantly less expensive and faster that UPS or FedEx, which consider the U.S. Virgin Islands an international destination.

Nix the five year plan

Five years is way too long to wait to start living the life you want.  I suggest booking your one-way flight within six months (especially if you can make it happen on miles … bonus!).  In our experience, that was an ideal window of time from decision day to flying one-way to paradise.  We were able to smoothly transition out of jobs, run out a housing lease and sell belongings at a good pace.  We could wait out good offers for our extra items, but weren’t without things we needed too quickly.  Just don’t put it off for the distant future or some ideal life scenario.  Just seize a moment that you’re in a decent financial place to do something awesome with your life.


I’m often asked if island life gets old.  Do you ever take for granted that you live where people vacation?  No longer notice the ocean view?  That weather is warm in February?  The answer is no.  At least in my experience and that of most of my friends on St. Croix, I never tire of having my toes in the sand at least once a week.  I never drive over the bypass and don’t look at the breath-taking ocean views.  I appreciate every single day that I don’t wear sleeves (hardly anything in my closet has them!).  But what I appreciate perhaps even more than the incredible tropical environment … are the people here.  St. Croix is home to the most kindhearted and generous people I’ve ever encountered.  The laid-back and friendly spirit that abounds on this island may be my favorite part.

If you’re ready to make the leap to island life, contact Chris and Kerri Hanley, the experts on the USVI real estate market.  As the top broker on St. Croix year after year with license to sell on St. Thomas too, Chris is the authority on Virgin Islands real estate.  Download their free St. Croix Event Guide to pick a move date before an event you won’t want to miss!

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