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How to move to a Caribbean Island – A Step by Step Guide

Have you ever dreamed of moving to an idyllic Caribbean Island? You picture palm trees sawing over your hammock on the white sandy beach. People tend to see their crappy job and dream of moving to the islands, but they don’t know what it takes to get there. We moved to St. Thomas USVI one month ago today. I didn’t really find a source that had all the information I was looking for. I did find a few kind souls through social media who offered some help and advice. Overall, the process is difficult. Now that I’ve been through it, I’ll try to chronicle what it took so that I can possibly help others who are contemplating a similar move. Obviously, this isn’t going to be the same for every person going to every Caribbean Island, but this what I encountered when I moved to St. Thomas USVI in the summer of 2019.

I’ll break it down into a couple of headings:

  • Preparation – What you need to do once you decide you are going but haven’t left yet
  • Logistics of leaving – How you get you and your belongings to the island
  • Costs – what it all costs
  • Getting adjusted
  • Lessons learned and mistakes made

I think these topics should cover most of what people want to know. Let’s dive in!

Preparation

Picture of antique chair with garage sale sign taped to it.

There are a thousand things to be done before you can move to an island. I tried asking everyone I could find the same question, “What do I need to bring that I can’t get on the island or that will make my life easier?” About half of the people said “bring everything you can, including the kitchen sink!” and the other half said, “you don’t need all that stuff on an island, just bring the essentials”. Needless to say, I was left to figure it out for myself. I’ll talk about what we brought, what we purchased, and what I wish we would have brought. I put a tremendous amout of thought into all of this and I still wish we would have brought a few more things. But, first things first.

Before you can figure out exactly what you are going to bring, you need to get rid of all the stuff you know isn’t going to make the trip. This isn’t just a move, this is a purge. You are not moving across town, or even across the country, ou’re moving across an ocean. So, you don’t want to pay to move things you don’t need.

Documents – You’ve got to go through your box of tax returns (and other documents). I had stuff going back about 15 years which means I moved them to several different states even though I didn’t need them. Along with my documents, I also went through all of my old photos and got rid of about 30% of them. Things like old scenery photos, duplicates, etc. But don’t get rid of everything. You will need to be sure you bring things like car titles, bill of sale for vehicles, marriage documents, tax returns, etc. I will talk about important documents again.

Clothes –

You’ve heard before that we all should get rid off what we haven’t worn in 6 months or a year, right? Moving to a Caribbean island is a great reason to put that into practice. You don’t need your whole closet in the tropics. But, before you decide to go crazy and donate all your winter clothes, think of your future vacations. You might want to change the tropics for the mountains when you have time off. Also, this is a good time to make a list of what you might need that you don’t own (extra swimming suits, hats, shorts etc.) And, the hardest for me, you’ve got to pare down your shoe collection because you won’t need five pairs of cowboy boots, or dress shoes. I also didn’t pack my suits and I think I brought two neckties, just in case.

Household Items and Furniture – This is going to depend on where you are moving and how you are moving. Are you taking a container, are you just shipping some boxes, or are you shipping pallets? We moved into a furnished condo (which we kind of regret) so we just shipped one pallet of stuff. We rented our house in The States fully furnished so we left most of our belongings. Since the possibility of returning could be a reality, we didn’t ‘burn the boats’. If you’re selling a house or leaving a rental property you’ve got to decide what you are bringing and what you are just getting rid of. I should also note that since we rented our house we were able to put a lot of things like power tools and camping equipment in the attic. If this isn’t an option and you don’t know if you will go back in a year or two you can get a storage unit, or try to get someone to store some things for you.

Sports Equipment– This was a tough one for me too. Your favorite golf clubs or fishing gear… what will be its fate? The hurricanes of 2017 destroyed the only golf course where we moved so I sold my clubs. Most of my fishing rods did not fit on a pallet which had to be 4’X4’X4′. Kayaks, paddleboards, surfboards, all too big to ship. Our condo has tennis courts so I brought the rackets that I haven’t used in about 30 years. I’m a bit of a packrat so I wanted to bring everything in this category. After some heated discussions, I relented because we were moving into a small condo and we knew space would also be limited.

Electronics – Are you going to bring your 70-inch flat screen… probably not. If your laptops or computers are old I’d look at replacing them before you go. Cameras, Ipads, phones, bring them all and think about updating them as well. I’d consider bringing speakers and a receiver if you’re an audiophile of any kind. I brought a very good Bluetooth speaker. I wish I would have upgraded my old GoPro Hero 3 before we left. My snorkeling footage isn’t great. And now I wish I’d have brought my entertainment set up.

Vehicles – A big question for anyone moving to an island is whether you should ship your cars or buy new ones on the island. After thorough research and asking many questions, we found a 100% consensus: bring your own car. The roads on St. Thomas are horrible: skinny, full of potholes, steep and winding. They said the island tears cars up fast and anything you try to buy here is going to be a peice of junk. Unfortunately, the vehicles we had would not have made good’ island cars’. We had a BMW which was to low to the ground to handle the bad roads and a big truck that I didn’t want to drive on the skinny roads. We sold them both and bought two Subarus. After much thought I decided they would be the best island cars. They are skinny, have great ground clearance and they have the all-wheel-drive for the steep hills. I was told parts wouldn’t be a problem and mechanics would be fine working on them. You need to be sure to ask those questions before you pick a car to bring.

Now that you’ve gotten rid of all the things you don’t need, it’s time to purchase the things you are going to need.

Here is a list of things we bought to bring with us.

Here is a list of the things we brought that were great ideas because they are either very expensive or you can’t find on the island.

  • Good Sheets (Kmart has cheap ones for $30)
  • Full Face Snorkel and Fins
  • My 4 piece fishing rods and I brought all my lures, line and all of my reels and tackle boxes
  • Stainless Steel glasses. We have big ones, small ones, wine glasses, mugs, you can’t have enough of these
  • Rugs – We have rugs from our travels around the world and they really make our little condo feel more like home.
  • My soft-sided cooler. They have hard regular coolers here even Yeti knock offs at the Home Depot, but I haven’t seen a decent soft cooler. I also brought a cooler backpack that will come in handy.
  • Dry bags – great for the beach
  • Hair bandanas– The wind is always blowing and I don’t like wearing a ponytail all the time. I feel like they are making me go bald faster than I need to. I bought about 20 of these before I left and it was a good idea. I also wear them under my snorkel mask, and it keeps my mask from pulling out my hair all the time.
  • Cosmetics/Lotions/Potions that are name brands that you like. You can find brands like Herbal Essence shampoo but anything “specialty” you will need to bring or be willing to pay shipping cost. Keep in mind that shipping can be as much as the item costs.

This is a list of things I wish I would have brought. You will notice that a lot of these items are preceded by the word “Good”. That is because you may find the item here on the island just not a high quality version of it. If you like nice things you will need to think about which ones are important to you.

  • Good Kitchen Knives
  • Nice Wine Glasses
  • A Good Blender
  • A Good Coffee Maker
  • Pressure Cooker
  • Electric can opener
  • Chocolate
  • More Bikinis (I told her to buy more)
  • The little flavor drops for water (I think the water here doesn’t take good and they are expensive here)
  • Better Yoga Mat
  • I wish I would have upgraded my old GoPro 3 (I just ordered this one to replace it)
  • Speakers/Sound System for the TV/living room

This one is a list of things we had to buy, and we didn’t expect, when we got to the island. Keep in mind we moved into a fully furnished condo.

  • BBQ grill (this was the first thing I bought)
  • Dehumidifier
  • Hangers
  • Coffee Pot
  • Blender/Food Processor
  • TV (the one in our condo was like 19 inches)
  • Air Fresheners (A LOT- our place smelled like mold and we spent a week scrubbing it)
  • Water filter (like a Brita or Zero Water)

Logistics of Getting to the island.

Moving to an island

Once you’ve sold the stuff you don’t need, and bought the stuff you do need, now you have to figure out how to get it all to the island.

Now it’s time to start calling around to get shipping quotes. We were told a shipping container would cost about $7,000. We were also told the cost of shipping cars is roughly $2000 each. Naturally, our first thought was “We will just put the cars, kayaks, paddleboards, surfboard, AND everything else we own in the shipping container, and we could get it all there for Six Grand.”. But it can’t be that easy. We found out they don’t let you put the cars in the shipping container. So, our next bright idea was, “We will put all of our stuff in our cars and strap kayaks on top of them and then we then can do it for about $4,000 when we ship 2 cars”. Nope! Not even close. They don’t let you put anything in your cars, let alone strap a kayak on top of it. You have to ship the vehicles empty.

Ultimately, we ended up deciding to ship two cars, to take two suitcases each on the plane, and to ship one pallet (The dimensions per our quote could be 4x4x4). I’ll break down all of the costs in a separate section. You have a couple of different options for shipping companies. A few of them are Crowley, Tropical, St. Thomas Cargo, and AWNA. My advice to read lots of reviews and talk to each company before you make a decision. I don’t this is a situation where you want to pick the cheapest provider. We used Crowley for the cargo and AWNA for the cars.

Shipping the cars and the cargo was a bit of a chaotic mess for us. Both the cargo and the cars ship out on Thursdays, but the cars must be at the dock in Ft. Lauderdale on Monday by 10 a.m. and the cargo must be at the warehouse in Miami by 2 pm on Tuesday. Keep in mind that neither port is open on the weekends. If you are going to be shipping out of South Florida your best bet would be to drop everything off on a Thursday or Friday. Then you can head to the airport and start drinking umbrella drinks.

But our schedule just couldn’t work out that way and this is where the chaos began for us. We had to leave for Ft. Lauderdale on a Saturday morning and drive 10 hours. On Sunday we rented a big van and loaded our cargo in it. Monday morning we drove both cars to the port and dropped off one car. Then, we turned around and drove back to the hotel to get the rental van. Next, it was back to the port again to drop off the other car. Finally, we drove the rental van with the cargo to Miami. After dropping off the cargo it was back to the hotel in Ft. Lauderdale for a well-deserved umbrella drink. I booked the plane tickets for Wednesday instead of Tuesday in case anything went wrong. That way we had an extra day and we wouldn’t miss our plane. Tuesday was the first day in a long time we didn’t have anything to do. We thought we would treat it like a vacation day. But, once again our plans were foiled, as it rained cats and dogs all day. So we got to know our hotel bartenders better as we had time for even more umbrella drinks.

Couple in beach bar with ocean in the background
This is us in the hotel bar.

You are going to have to live for at least a week with whatever you bring in your suitcase. If you are lucky your cars got on the first boat out and so did your cargo, but their is no guarantee. If they didn’t you will be waiting two weeks before your belongings arrive.

We had a rental car lined up for a week when we got to St. Thomas so we could get around the island when we arrived. We knew we were going to need to get supplies and stock the fridge. We toyed with the idea of just taking a taxi to our condo and then a taxi to the grocery store for a food run. We naively thought we could live without a car for a week and lounge around on the beach. But we needed to make ten trips to the three different grocery stores and five trips to the Kmart and about ten more trips to the Home Depot. Our condo wasn’t exactly turn-key. I should also mention we had never even seen it, my wife’s boss went and looked at and told us it looked fine. Needless to say, the rental car turned out to be a very good decision.

Here is a breakdown of our moving expense.

Vehicle Transportation and Registration

  • Car Transport $1600 per car to ship them. ($3200 for two cars)
  • Road Taxes are $.16 per pound. Each of our cars was about 3200 pounds $384 per car ($768 for two cars)
  • License Plates $175 each ($350 for two cars)
  • Registration $525 each ($1050 for two cars)
  • Driver’s licence $55 each ($110 for two people)
  • Car Insurance $1100 for a year for both cars

Plane tickets and rental cars

Obviously, this will be different depending on where you live. We lived in Panama City Beach, FL so we drove to Miami. I’m not going to include gas to get to Miami and meals and that sort of thing. Here are our ‘other’ expenses.

  • Hotel in Ft. Lauderdale for 3 nights $435
  • Rental car in Miami for two days $207
  • One way plane tickets out of Ft. Lauderdale to St. Thomas $169 each ($338)
  • Checked bags an extra $80 (they were overweight)
  • Rental Car in St. Thomas for a week $350
  • Cost to ship one pallat that weighed about 500 pounds $283
  • Then in the first week, we spent about $1500 on groceries, buying cleaning supplies, and supplies for the house
  • We pay $1,900 a month rent for a one bedroom condo. We had to pay first month, last month and one month as a security deposit. So that was $5700.

There was also, eating out in Miami and Ft. Lauderdale, and entertainment and gas along the way. But excluding those things, the expenses I’ve detailed total. $15,471.

Other expenses not mentioned are that we sold both of our cars and spent a little more than the money we got for them. That is a couple of more thousand dollars. Also, you will probably have some time you are not working, so you will need to factor in that loss of income. And, there is the stuff like clothes, snorkels and all the things we bought in preparation of moving.

We did make some money selling stuff before we left, but since we rented our place fully furnished we didn’t sell furniture and big-ticket items like that. It was more like garage sale type stuff. We probably sold $2500 worth of junk we didn’t need ($1100 of that was my Hobie kayak).

Getting Adjusted

Everything is a bit more difficult in the Islands. We expected things to be a little harder here and I think that expectation was a good thing. Going to the DMV (which here is called the BMV) is an all-day affair. You need to go to 3 different stores when you go grocery shopping because one store never has everything you need. You drive on the left side of the road. Roosters crow at all times of the night and day. I’ve lived in a lot of different places (all in the US) and my wife is from Spain and she lived in Denmark, and Nigeria before moving to the US. We’ve also traveled to many different countries. But living somewhere is different than visiting. When you’re on vacation and the power goes it, it’s different than when you are working in your office and there is no internet for who knows how long. Things like roosters crowing and power outages may sound quaint but can be quite annoying.

We are both pretty frugal, but there are a few ‘nice things’ we enjoyed and that we had in our lives before moving. Here you just don’t get too many ‘nice things’. You have to learn to make do with what you have. If you tend to be a person who complains a lot, this might not be a good place for you. You have to be able to roll with the punches and adapt. If you want to lose the respect of an Islander tell them “How you did it stateside”. They will roll their eyes and walk away from you.

Island Time is a real thing. Here is a perfect example, our stove and washing machine were broken when we moved in. The repair guy didn’t call back for a day so I called him a second time, no answer. He called me back two days later. When I got off the phone with him and my wife said: “Is he coming today or tomorrow?” I chuckled and relayed what he told me “Maybe I come Saturday, but if not then I come later, but don’t worry Mon, I come”. He did show up on that Saturday and he said “I’m gonna need some parts to fix dis tings, I be back” and we haven’t seen him since.

Everything is more expensive. You just have to adjust to the prices. Our first few trips to the grocery store my wife would say things like “I’m going to splurge and buy coffee”. I told her eventually we will just call it “grocery shopping” and not “splurging”. You have to try not to compare prices to what they were stateside. The prices are what they are. But, they also vary widely from store to store. Peanut butter might be $7 at one store and $4 at another. You have to learn where to buy what. Finding good vegetables is very difficult. They don’t grow anything on this island and by they time vegetables get here they don’t have much time left before they have to be eaten. They are also very expensive. Asparagus for example is about $7 a pound.

These are some costs of some things that surprised us.

  • Butter $8/pound
  • Beer $35 a case
  • Cheese (this is one of those items you really have to shop around but generally expensive)
  • Juice expensive
  • soda expensive
  • a loaf of white Wonder Bread $7. But they some local coconut bead for about $3.50
  • Chocolate is expensive
  • Veggies are expensive and horrible. They don’t really grow anything on this island so finding veggies is a challenge and if you do, they cost a lot.
  • We needed a cutting board and a cheap plastic one at Kmart was $15
  • We couldn’t find a clothes hamper anywhere and when we finally found cheap plastic one it was $30

Some things are the same. We have a Home Depot and pretty much everything in the store was the same price as it was stateside. Beef and pork are about the same price but chicken is more expensive. Liquor is cheaper and wine is about the same, maybe 10-15% higher.

We also found a thrift store and now I go there to look for things first. We bought a cutting board there for $2 and box fan that was $30 at Kmart was $15 at the thrift store. You have to learn to be resourceful.

Some other essentials we pay for:

  • Cable $80 a month (which we decided to turn off we anticipated this move, that is why we bought a Fire Stick before we left the States)
  • WiFi $50/month
  • Rent $1900 for a one-bedroom condo on the beach
  • Power (haven’t gotten our first bill yet but we are scared)
  • Water and Gas on our first bill was $90 for our first month.
  • Car insurance $1100 a year for a 2006 Subaru and a 2010 Subaru

Lessons Learned and Mistakes Made

One of the first things we learned was that getting the cars to the island was a bit more complicated than we anticipated. You have to run around and go to one government office and pay a tax then go to the port and do something else, and then go to the DMV for another thing and then to another place. It is a chaotic sequence of events. When trying to get our car tags we had our car insurance info on our phones but we needed a printed copy, and he only place to make a printed copy is a 15-minute drive away. After driving to print out the insurance cards we returned to the DMV to find it closed at 3:00 and we expected them to be open to 5:00 and so we had to come back the next day. Then we found out you had to have an inspection done on your car, but the inspections end at 1:45. I might do a whole post on how to get your car through customs and registered in St. Thomas if anyone is interested. Without having the rental car to run around and jump through all of the hoops it would have been next to impossible.

We also didn’t know how much we needed to shop around. At first, we just figured the Kmart was going to be the cheapest place to buy things. We bought things like a mop ($30) and a simple coffee maker ($32). We later found them cheaper at Home Depot. We got smarter with our grocery shopping and started to make a list of the products we like at different stores to figure out what to buy where. We didn’t find the PriceSmart for about two weeks, it’s like a little Island version of Costco. But they have some good deals there on certain products. You pay $25 a year for a membership. And like I mentioned before, don’t forget about thrift stores. When people leave the island they tend to not take things with them. Most people leave in the slow season so it’s easier to find apartments and stuff at the thrift store during this time.

To receive the cargo, we paid Crowley an extra $40 to pass it through the customs and do all the paperwork. Probably a good idea to just let them handle it for $40. I wish they would have done the cars for us too.

It was definitely a good idea to rent a car while we waited for ours to arrive. We had a lot more running around to do than we thought. Budget Car Rental was the cheapest on the island and in Miami. Just be prepared for the car you get in St. Thomas. If you get the cheapest car you can get from Budget in St. Thomas, you’ll be surprised how bad it is. Worse than anything I’ve ever driven. But a good lesson on “you don’t need fancy stuff on an island”.

Another frustrating delay was that to get our driver’s license we needed our driving history. Which we could have gotten from the DMV in Florida. But since we didn’t know we needed it, now you have to either mail in a form to Florida and it takes 2 weeks, or pay $30 and they will email it to you. Just one of those little things that is frustrating that we didn’t expect.

Other documents you will need. Bill of sale from when you bought your car. We got through without one, but they made it a bigger pain in the butt on us for not having it. Printed Insurance cards, Social Security Card (original). Passport, Driver’s License, and that Driving History. I don’t think they asked for birth certificates.

We wish we would have rented a non-furnished Condo. The furniture in our unit is terrible. The mattress makes us wake up with our back like a pretzel every morning, the cushions on our wooden couch are 1.5 inches thick. The dressers and wood furniture smelled like mold. After googling how to get the smell out of wood, we spent a week rubbing them with Vinegar, then Vodka, then buying charcoal air fresheners to get the smell to the level we could tolerate. And any furniture we replace we will have to leave for our landlord. We only have a six-month lease but we are buying a new mattress and a few other things we need to live comfortably.

Other things that surprised us

  • We were also surprised by how nice the people are. Some of the Social Media sights I was on made me scared that everyone was mean and cynical. But the people are very nice and helpful.
  • You don’t need a fishing license in the USVI
  • Hard to find authentic food (at least so far)
  • Water tastes bad (to me, the wife doesn’t seem to mind it)
  • Finding ‘Nice Things’ is difficult, everything just kind of seems to get you by
  • Seems to be a little harder to make friends that I thought. But we’ve only been here a month. They don’t like newcomers and they think no one has the cojones to last here, so people don’t want to make friends with new people (that is what a guy at the bar who has been here for 18 months told me last night so don’t give me a bunch of grief for saying it)
  • Parking sucks everywhere
  • Zero information to be found on fishing or fishing tips (without going out on a charter)
  • The amount of trash everywhere is disappointing
  • Being this close to the equator it is always dark by 7 pm. Just not something I thought about before we got here. No more long summer days. But I guess that is OK since it’s always summer.

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The Best Beach Hacks for long hair at the beach-For Guys and Gals

Girl holding hair on the beach

There seem to be a thousand articles about beach hacks that are full of useless information. But even in that sea of useless information, I haven’t seen many good articles with simple tips and tricks for long hair at the beach. I see articles that either has some regiment of 12 products you need to put on your hair in the morning, then in the afternoon, after you shower, before bed, and then repeat. I’m never going to do all of that. And I don’t want to put avocado and mayonnaise in my hair either. I just want some quick things I can do to protect my beautiful locks and help me keep it from being so tangley. I put together my list of what I think will help your long locks at the beach. I think these are good for both the beach bunnies and surfer dudes.

This is the second time I’ve had long hair. The first time I was 20 and my I was in college and my hair was think and the envy of many girls. I didn’t give it much thought and I didn’t really take care of it. After college, our society said I had to cut it off. Now I’m 45 years old and I don’t really give a shit what people think anymore. I haven’t had my long hair for very long and I’m a little concerned that my long hair is making me go bald even faster (mainly because every time I see my Mom she tells me a story about how her sister had long hair and it started falling out so my long hair is going to make me go bald). So I’m always thinking about what I can do to keep my awesome Fabio looks and prevent my hair from falling out.

This list is not based on any scientific research and Paul Sassoon didn’t give me any money. But if he offers I will take it an I will write a whole other article based on whatever he wants me to say. This is just based on what I’ve found that I think makes my hair happy and some ideas my wife came up that makes her hair happy.

It’s funny because everyone who envisions a Beach Bum sees a guy with long hair. Look into your mind’s eye and picture the epitome of a surfer… long hair right? But the truth is that the beach and long are a horrible combination. Ski Bum and long hair is a much easier life to live. I did the ski bum thing for 10 years, I’m over the cold weather. So, here I am living in the islands and I’m loving the look of my long hair. But it is a huge pain in the ass. So, here are the ideas that we have come up.

I think the best idea I came up with is wearing a seamless bandana. It’s basically a tube top for your head. I pull it all the way down on my neck, pull my hair through it, and then push it up like a headband. But, if I want my hair more out of my face I can extend the top of it to hold my hair farther back. It also keeps my hair off the back of my neck and keeps me cooler AND, it also acts as a sweatband if it’s hot (which it always is) it keeps me from looking sweaty. It also keeps the sun off my hair and protects my scalp. I felt like the ponytail holders where killing my hair and wanted something more gentle. And, I don’t think a scrunchy was the look I was going for. So this is the solution I came up with. You can wear it like a bandana like Axle Rose or make it longer and it holds your hair back more out of your face, and there is nothing pulling and tugging on your hair. After I got to the island I noticed lots of long haired dudes were wearing the same thing. I was shocked because once again I thought I invented a new fashion and everyone was already doing it.

If you have very thick hair or super long hair, like my wife, then putting it up or in a loose braid might be a better option. It will keep it from getting tangled but won’t put too much pressure on it like a tight ponytail or french braid. Remember it’s all about reducing the stress on your hair. The sun, sand, heat, salt, and wind are all working against you. So we want to find ways to make our hair happy.

Ditch the hairdryer and the flat iron. Your hair saw enough wind and heat on the beach. Let it air dry. Those natural curls will make you look beachy and carefree. Plus you will have more room in your suitcase for shoes, or more souvenirs (like rum).

Try not to wash it too often. Be sure to rinse and condition. A leave in conditioner would be even better. The sun and heat want to dry out your hair and washing it will strip away more of the natural oils. So keeping it moisturized will keep it healthier. There some ‘au natural’ things you can use as well. If you mix apple cider vinegar with water it makes a natural conditioner. Also, Cocoa Butter or Shea Butter are great for your hair. They will help to reduce frizz.

ProTip – If you’re are a blondy who gets green hair from the swimming in the pool, if use the apple cider vinegar and water it will take the green out. And if you wet your hair before you get into the water it helps reduce the amount of chlorine your hair will absorb.

And finally, I’m sure everyone with long hair knows this one, but be sure to use a wide-tooth comb or pick. I like to comb my hair in the shower when I have the conditioner in my hair if it is particularly tangled.

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