Updated 2023

Let's talk about what you really need to know about traveling to the Caribbean. Sure, there are plenty of tips for tourists and information from hotels out there, but here's what often gets left out from two type A, efficiency lovers.

While I've been to the USVI and BVI a handful of times, Chris had been going for weeks at a time each year since he was a small child, attending sailing camp and generally creating an appreciation for crystal blue waters and white sandy beaches that would keep us away from any state side beaches ever (the perks/curse of my in-laws living in St Thomas! Chris's Mom and Grandma live there). That being said, there's been a gap since we had been down owing to the fact that our boss is a real hard ass when it comes to vacation time and salary (#selfemployment). After finally scheduling a full week to head down again, we realized that this has to be a regular part of our life from now on. So we took notes about how to really streamline our travel there. Seriously.

1.Bring Your Passport

While the US Virgin Islands (St John, St Thomas, St Croix & Water Island) are US territories if you want to boat over to the British Virgin Islands (BVI) you obviously need a passport. If you plan on taking a boat out and crossing into foreign waters, you're going to need that little blue book. If you are visiting the USVI for more than 4 days, we highly recommend popping over to the BVI to see the Baths on Virgin Gorda and of course Soggy Dollar bar on Jost Van Dyke (you park your boat and swim to shore. You've GOT to get the mahi mahi salad, chicken roti and a painkiller cocktail). If you have a child, remember to get them a passport as well, or at minimum some form of identification for leaving the island to return to mainland US through customs at the airport.

British virgin islands , soggy dollar bar

2. Take day one REALLY slow and easy

You're going to be really tempted to jump right in, go to the beach and drink a lot of rum. Don't do it. Really. For most of you, it's going to be a massive change of climate and sun. It's easy to over do it, get over heated, sun burnt, dehydrated and realize you haven't relaxed in, oh five or so years. Day 1 of this trip really killed me. Night one was spent throwing up and I feel asleep on the tile floor. And to clarify, it wasn't the drinking (seriously). Depending where you are staying, a lack of a breeze will really weigh you down and make you feel stuffy and uncomfortable. Your first day there, sit in the shade, drink lots of water, and know you have the rest of the vacation to be in the water and sun. Never underestimate how quickly the sun and booze can sneak up on you. I’d highly recommend a sunshirt and hat 90% of the time.

3. The St Thomas airport can give you a heart attack

The cool thing about the USVI is how different each island is. St John is mostly a park (no airport). St Croix is practically a flat sandbar. St Thomas on the other hand is a hell of a lot of hills and mountains and it can take you a LONG TIME to drive it (on the opposite side of the road mind you). But the thing about those mountains and the length of the island? You have to land a plane there. Just as a word of warning, landing is going to look like you're going into the water and they put the brakes on FAST. It's not smooth. And take off is worse in my opinion. So FYI, it's going to feel different than a normal airport. Don't freak out (or just keep your s*** together for 10 minutes).

I also feel the responsibility of letting you know that you need to get to the STT airport MUCH earlier than you think to clear customs. If you’re taking a morning flight, customs can move more quickly (despite only 1-2 agents being available), but in the afternoon it’s not uncommon to stand in the customs line for 1-2 hours. Even if you have global entry (which we do), there is no guarantee the global entry line will be open (it wasn’t).

4. Pack less than you think you need

For a week, we each packed a carryon suitcase. Editing this post years later, traveling WITH a toddler, we still only packed two carryon bags and three ‘personal items’. We do have a washer and dryer there but even so, you're not going to need as many outfits as you think. I only used two swim suits (one could dry while I wore the other one), 2 loose tank tops (you're not going to want clingy), a sun dress in light fabric, a short sleeved/shorts romper, 1 pair of shorts and a v-neck t-shirt plus a hat, flip flops and sunglasses. Our agenda was 1 day boating, part of a day out and the rest was beach. Honestly, I could have gotten away without the dress too. But don't forget reading material if that's your thing. Again, I highly recommend a sunshirt/rashguard or two.

5. Make sure your cell provider works.

We have Verizon at home, but that network was faulty at best in STT with extremely limited coverage on Water Island. In recent years it has gotten better (extended network) but in the past we had to buy an AT&T sim card. Now, with wifi being mostly everywhere, this is even less of a problem.

6. NEVER buy your rum at a tourist shop. Go to the grocery stores.

Rum is one of those things people who visit love to bring back. In fact, you can actually bring a small box of rum as part of your carryon back home. But if you buy it in a tourist shop, you're going to get ripped off. You can get it for much cheaper at the local grocery store the locals do. Can you imagine if everyone on the island went to the tourist section of town to get their liquor?

7. Always say good morning/hello.

The number one way to tell if someone is a tourist on the island is if they are a jerk (and you're pale as hell). EVERYONE says good morning/hello. If you walk in a shop, say it first. It's part of doing business. And sometimes, you're going to get a little discount for being friendly/local. Just saying. Be a good human. Please also remember you are now on island time. This are much slower here. If you are from the East Coast, this is going to drive you nuts the first time until you remember to stop. Enjoy the view. Enjoy the weather. YOU'RE IN THE ISLANDS! A great way to pass the time is to chat with the cashier/bartender/waitress. They all have fascinating stories. We met one guy who used to live in the South, found a Craigslist ad to manage a bar in the islands 7 years ago and they hired him within 30 minutes of him sending an email.

8. Direct flights do exist.

United flies direct from the DC area to St Thomas in under 4 hours. IT'S MAGICAL. Typically airlines would make you fly to Miami or Puerto Rico and hop on there. But God Bless United. Interestingly enough, when I was at JFK airport in New York oh Thursday coming home from a different trip, I talked to three girls who had just come back from the islands-->Puerto Rico--> JFK and were then flying to Dulles. No freaking thank you. I'll take direct for $20 more dollars.

9. Go to the BVI early in the morning.

It might be tempting to sleep in, but if you're island hopping we recommend starting the day early! By the time we got to the Baths, there were a few tourist boats already in and going through the rock formations. If you go early, you're going to be able to enjoy it at a slower pace with less people and even better pictures. Part two of this recommendation is to avoid the rush back to US waters. The customs office closes around 5 so a charter is going to rush to get you checked out of the BVI...the same time as all the other charters. So think about it this way: you could wait around with everyone else, or you could get more out of your day by starting earlier.

10. Food is expensive: Cook when you can

Okay two things here. Food is expensive. You're going to absolutely balk at prices. I bought grapes for $11 in 2017. In 2023 it was even more insane. I highly recommend considering staying at a place with a kitchen and taking the time to meal plan/build a grocery list. We tended to eat 2 meals in and 1 meal at the beach (there are a few beach side options in Cowpet where we stay). But one of our changes for next year is we're going to cook more at home and eat out less because honestly the food is not stellar. It's just not. There are a lot of fried things and the only thing we can give major thumbs up for is mahi mahi and blackened or jerk chicken (and not every place does it well). With a toddler, we actually brought some food with us for flight/comfort food snacking (crackers/cookies/vegemite/noodles etc).