What to Pack for a Crewed Caribbean Sailing Trip: Essential Items

If you are heading on a sailing vacation in the Caribbean, everyone hopes to hit the “sweet spot” between packing too much and not enough.

We are going to help you with what to pack for a crewed Caribbean Sailing Trip. Packing light is vital, but what does packing light mean?

Even our list has 25 different items to consider packing.

Packing List

Soft-sided luggage. Storage space is at a premium on anything but a superyacht.
2 Swimsuits
Six t-shirts and some underwear.
If you are female, you probably want a sundress or two that can double for going out for dinner.
Males may want a short-sleeved nice shirt, again, for going out to fancier places for dinner.
A long-sleeved shirt for protection is a good idea. I also recommend a snorkeling Shirt that is quick drying.
A light rain jacket. If you are in storms, you cool off quickly if you get wet + windy. Your rain jacket also doubles as a light coat if you get chilly in the evenings.

Wearing shoes on your Crewed Caribbean Sailing Trip

Two pair of shorts plus the ones you are wearing when you get to the islands
One pair of sandals or flip-flops, perhaps only the ones you wear on the plane. You need to be able to get them wet. You will mostly be barefoot on the boat.
Socks. For traveling back and forth to the islands.
Make sure your footgear won’t leave black sole marks on a boat.
If you have shoes that are not good for getting wet, then bring a pair of water shoes as well. It will come in handy, getting to beaches.

What to bring for your enjoyment on your yacht charter

Beach/Sailing Music (my iPhone)
Reading material (Kindle)
Your own small personal dry bag. You know it is dry (hopefully), and you don’t have to share!
Mask & Snorkel. If you wear prescription lenses or have a comfortable, well-fitting mask and snorkel, bring it.
Towel – Bring one of those “light skinny towels.” Even though your yacht will have towels, they don’t dry as quickly, and I often find this little towel handier for taking to the beach, etc., as it takes up so much less room.
Earplugs. If you have problems sleeping, a disposable pair for boat noises may be handy.
Refillable water bottle. Insulated preferred! Most of the crewed yachts now offer water bottles to their guests, so it is not a big deal. I have noticed though that most of the water bottles on the crewed yachts are NOT insulated

Don’t forget

Chargers/batteries for electronics
Cel Phone/ International Roaming Package/ Local SIM card as you prefer. Quite a few of the restaurants and beach bars will have complimentary wifi, and virtually all of the crewed charter yachts will have the internet onboard, good enough for email, Facebook, and the like, but not for streaming video. Ask if your yacht has STARLINK on it!
Motion sickness? Get a prescription for Transderm Scop, or bring Bovine, ginger, or wristbands. Generally, this settles down if you are prone after the first 24 hours
Money and credit card: All but the tiny beach bars take credit cards. American Express is NOT as accepted. Although ATMs are on significant islands, there is not a lot, and they are often out of cash on a Sunday.
Passport and travel documents. Yes, even though you can fly to the USVI as a US citizen without a passport, you will need one to go into the British Virgin Islands, for example.
Any medication that you take daily and a prescription list never hurts, either.

Sun Protection for your Crewed Caribbean Sailing Trip

The cockpits should all have good shade. But everywhere else you’re getting direct sun plus the reflection. It’s like being in a sun broiler.
Two pairs of sunglasses. (1 spare) Must be polarized. Have a lanyard with them, so they don’t disappear, even better!
Hat – to keep the sun off your head all the time.
Nonspray sunscreen. Spray-on sunscreen on the boat makes it slippery for everyone as most ends up in the air or on the decks. Unless you have favorites, I tend to find there is usually plenty on the crewed yachts—generally what the guests the week before left!

Many destinations are starting to ban the import of sunscreen protection that has harmful chemicals such as oxybenzone, octocrylene, and octinoxate. The ban includes the US Virgin Islands, which is a territory of the United States.

These are three UV-blocking chemicals found in most mainstream commercial sunscreen products in the United States.

What happens if my luggage does not arrive for my sailing trip?

Your luggage not arriving with you is not uncommon. Especially on small islands and if you have connections. In all the trips we did, the luggage did eventually catch up with us that week. On the airline’s dime.

Make sure you have the yacht phone number as well as your own when you fill out your lost baggage claim at the airport. In most cases, it will be on the next plane. They will taxi and ferry it to a closer point for you to pick up.

Lost Baggage is a great reason to keep a swimsuit, a toothbrush and your medications you cannot live without in your carry on bag!

You get bonus points if you can keep your packing down to just a carry-on!

This list is not exhaustive, and please remember to bring your sense of adventure. You are going sailing. Your yacht crew will have more things tucked away in a corner that they can help you with than you can imagine!

I hope you find out page helpful on What to pack for a Crewed Caribbean Sailing Trip. We have plenty more tips for you on our Yacht Charter FAQ page here

Or check out a series of blog posts we also have on Yacht Charter FAQ

Enjoy our blog post on Caribbean Sailing Trips here and then contact us to book your amazing vacation