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Caribbean Vacation: The Best Packing List for a Sailing Vacation

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If you read our previous review article on Caribbean Sailing Schools [find here] then you might be wondering what's next? Well, we thought it would be a great idea to come up with the ultimate packing list for a sailing vacation in the Caribbean.

So you are ready to vacation in the Caribbean?!? Yay, now what to bring?!?

Let's get you ready for the trip of a lifetime where you will learn to sail while vacationing in the Caribbean islands. Did you know that there are over 7, 000 Caribbean islands to explore?

Most of the Caribbean sailing schools we mentioned in our previous blog post were located in the U.S. and the British Virgin Islands. You can find more information by visiting the US Virigin Islands and the British Virgin Islands travel websites to explore the island chains, culture, food, lodging, beaches, restaurants, etc.

If you are still debating about a vacation in the Caribbean for sailing school, then read this article first. There are so many beautiful islands in the Caribbean to choose from and to cruise around.

Alright, let's get back to the packing list for a Caribbean vacation sailing school.

Let's begin with packing tips:

1. Check the weather prior to arrival.

2. Know the currency.

3. Check your sailing school's website for "what to bring" information.

4. Check your government's travel alerts.

Packing List Categories

Let's break down the packing list categories for your sailing vacation in the Caribbean that you will need target:

  • Clothes/Accessories

  • Toiletries

  • Electronics/Gear

  • Documents

  • Food

  • Luggage/Carryon/Backpack/Purse

Now let's review the following packing list is suggested for a seven-day liveaboard sailing school vacation.


Active tops (long sleeve and short sleeve)

Active bottoms (shorts and long pants)

Traveling outfits at least 2

Bathing suits & Cover-Ups




Lightweight Rain Jacket (We reviewed a women's lightweight rain jacket here)

Sailing Gloves (Check your sailing school's website, they might provide these)

Boat Deck Shoes (We previously reviewed a pair of women's boat deck shoes here, or you pack sneakers with light-colored soles and socks)


Flip Flops

Polarized Sunglasses




Lip Balm



Shaving Supplies

Medication (It's a good idea to bring motion sickness relief just in case)

Hairbrush/ Hair Products/ Hair Accessories (Leave the hairdryer at home)

Bug Spray


Chargers for all electronics (Plugs are the same as in the US)

Camera/Video Camera

Snorkeling/Diving gear (First check to see if your sailing school provides this)

Beach Towel


Flight/Travel Itineraries


Sailing School Information

Medical Insurance Card


Dry snacks for traveling (granola bars, snack mix)

Reusable Water Bottle

Most of the Caribbean liveaboard sailing schools that we reviewed in a previous blog post [read here] provide onboard meals. However, you will need to purchase your drinks/meals when on land.






Now you may be thinking this list is exhaustive, we think it's better to be over-prepared than under-prepared when going to the Caribbean islands for vacation. Some items might be hard to come by if you forget, so we tend to overpack.

We hope this Caribbean sailing vacation packing list will help you have an amazing trip while feeling prepared and organized.

Bon Voyage!

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Sailing Clothes and Gear started out of love for sailing. We hope to pass our learned knowledge of boating on to our readers by reviewing, recommending, and providing education by writing articles.  


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