Checklist: Moving a family to the Virgin Islands
- Debbie
- Aug 23, 2019
- 5 min read
Updated: Sep 10, 2019
This is the top question I get when I tell people our family is moving to the Caribbean. People say "you are living the dream" and hope I can provide answers or a path to finding a way to do the same. If you are looking for that type of checklist, I need to be a Debbie-downer (pun intended) - this will not give you what you are looking for. There is no clean checklist that will tell you how to move to the Caribbean (believe me, I Googled high and low - and there is not one that will suffice). Everything is very personal and situation specific. So, in an attempt to share our journey to our move, here it goes:
1. Let go of being in control, and embrace going with the flow.
If you are seriously considering moving your family to the Caribbean, the first thing you need to do is let go of trying to control everything and be willing to bend with anything (and there will be *many* things) that is thrown your way. For those of you that know me well, this was probably my biggest challenge - and honestly is an ongoing journey. I constantly have to remind myself that I have the ability to respond well to anything thrown my way and stop stressing about every detail. The mantra I keep repeating to myself came from a conversation with my sister "Stop worrying! You are smart and always find a way to get back on your feet".
2. Stop dreaming and start crafting your plan
Early on, you will need to make the decision to move final and then everything else will need to fit around it. -
You may discuss the move to a simpler life for a few years in a whimsical way, but to make a decision you may need to convince your partner that this is a good idea. Oliver had to convince me.. This is how he did it:
Choose a time where you and your partner have a lot of uninterrupted time together (example: a long car ride). Show them a video summary of a family that took the leap and made it look so simple and convince them by the end of the ride that this is a solid idea (this is what Oliver showed me on a long car ride last Christmas - he actually reached out to this family to get details..please don't bombard them - ask me instead.).
Agree on core pieces necessary to be in place for the move to happen. For us it was: employment, schooling and housing and research for months!
3. Decide if you have a feasible plan. If you do, commit to doing it
Employment: Get a general understanding of what your options are for providing for your family. Will you be able to work remotely? Will you work locally? You may need to look at different locations to find what you are looking for (and USVI is not equivalent to moving to another state ini the US)
Schooling: Look for where you kids will go to school (or decide to homeschool). We were lucky to find a school that was a good fit for us on-island.
Housing/Location: Research cost of living and ability to rent for a year. St. John has scarce long-term rentals, so we had to make sure this was possible above and beyond anything else. Also, research infrastructure (internet/power) to enable remote work (if that is the path you are taking) Note: St John is mostly service focused, so not a lot of jobs available for my area of work (tech).
Random: anything that pops in your mind (usually at 2am and causes sleepless nights). How to get your dog to an island? What to do about healthcare on an island? How often do flights go to the mainland? Probability of hurricanes? What to do in a hurricane? Etc etc etc.
Pro USVI Tip: VIMovingCenter.com was a super useful resource!
4. Follow through, even when things get tough
Finalize what you will do for employment/financial security while in Caribbean. Maybe have some tough conversations with your boss/company. Be prepared that this will likely not work out the way you thought it would. Be willing to bend on things you thought were critical. This was not easy and perhaps the most stressful part. Remind yourself that no matter what happens you can adjust to that situation. Be flexible, but responsible.
Find a rental house to move to (we had to go to a local cork board in-person on St John to find ours - long-term housing is very scarce and St John has a culture of taking care of locals/on island first).
Register kids for school. We found a great one on the island that we are super excited about. Remember to get files from your current school and transfer them to new school.
If you own a house decide what to do with your house (we rented ours out with a broker..we tried Zillow for 2 months and had no bites!)
Plan for what to do with everything in your house. We did a MASSIVE yard sale (a lot of work, probably a month of prep), a pod for storage (we took 3 weeks to pack), shipped some things down and rented our house partially furnished.
Plan for what to do with your cars: we shipped cars (with Tropical) and leased out one to a friend. To be road ready cars need to be registered locally on USVI.
Stop and wonder if this is too crazy an idea..convince yourself you will regret it if you don't. Maybe Google hurricane preparedness again..
Plan for your animal(s). Rabies vaccination within 6 months and a health certificate from the last 30 days.. we also sent health records to a local vet on the island. Organize how you will get your animal there.
Do all yearly Dr appts: general, eye, dentist and any specialist. Get written prescriptions if you need them. Also, get copies of you and your kids health records.
Find a good reef-friendly sunscreen (I will have a whole post on our 3 month long experiment of every zinc sunscreen)
Freak out again about your plan. Likely have a few sleepless nights and lull yourself back to sleep and convince yourself that this is the right decision by staring at some turquoise waters, sea turtles and dolphins.
Get remote work scenario setup in your new home - organize internet setup for new home, if your home has a generator that is likely necessary as well.
Be prepared for everything in your life to go haywire (or maybe it just feels magnified because of your stress-level). Work will go absolutely nuts and require long hours as you are trying to move, air conditioning might break down during your yard sale when it is 109 degrees 🥵.. Your dog will start acting lethargic and/or your whole family might get the tummy bug while trying to pack bags that need to go on a container 😷
Schedule farewell gathering for friends and kiddos friends. Be prepared for tears. Be prepared for reflection on how great your life actually is. Also, be prepared that your kids will likely handle the change better than you.
Start a blog..because people will be curious about your adventure.. but not everyone, so create a private facebook group to post updates to those who opt-in so you don't lose friends that don't want to hear about the amazing weather every time.

All the best to you all! I do expect you will run across our son Jeff and his wife Katja who moved there seven years ago with two dogs- with no expectations that they will ever leave (unless another Cat5 moves through 😮 ) ...they LOVE it! We have met so many wonderful friends of theirs who live on island and have children at GHS - it’s going to be amazing for your family I’m sure! Hope to see you during our spring visit ... Diane Keleher- (Sarah K’s aunt) 😊