What To Pack For a Caribbean Crewed Sailing Trip?

Knowing what to pack can be confusing if you’ve never been on a sailing holiday. But it’s actually much simpler than you might thank. So, what should you pack for a Caribbean crewed sailing trip? 

You should pack sunblock, sunglasses, a hat, light, breathable summer clothing, and a swimsuit (or two) for any Caribbean sailing trip. You should also pack environmentally friendly toiletries, as they will end up in the ocean. The quantity depends on your boat’s size and the trip’s length. 

I understand that it can be daunting to know what to pack. So take these packing tips from a 10-year yacht crew professional that’s done several Caribbean charter seasons, where I’ll explain in a simple way and provide you with a comprehensive packing list.

This packing guide will cover what you need to pack for various types of crewed sailing trips in the Caribbean. I’ll discuss everything from small boats to much larger yachts. It’ll also include separate sections for men and women and a general packing list.

✔️ What To Pack For A Caribbean Sailing Vacation

This section will provide a breakdown of what you should bring on your crewed sailing trip in the Caribbean.

I’ll break it down into different sections covering boats of all sizes. This will cover clothes rather than other essentials, which I’ll examine in the next section.

One thing that tends to be overlooked is the bag you pack in. You should pack in a soft-shelled suitcase that can be folded up and put away due to the limited space on the boat. 


What To Pack For A Small Boat

The number of each item of clothing you take will depend on how long you spend on the boat. Pack to the number of days you have chartered your boat for. 

  • Bathing Suit (2-4): You’re on a yacht in the Caribbean, so you’ll spend a lot of time in the ocean. The more swimsuits you have, the better!
  • Rash vest: If you’re snorkeling, wearing a rash vest to protect your back from the sun will be a good idea. 
  • Smart Casual Outfit: You may want to go out for dinner (fine dining restaurants included) on the shore or want something smarter than shorts and a t-shirt in the evening. It should be light and breathable, like a linen shirt and linen trousers. For women, a nice-looking summer dress will work as a smart casual option. 
  • Shorts (1-2): Shorts aren’t essential if you’re happy to live in a swimsuit. But if you’d like something else to wear at times, then throw in some shorts. 
  • Sweatshirt (1): It won’t get that cold, but having something with long sleeves will come in handy. This is because it can sometimes get a little chilly at night. It doesn’t need to be heavy, and you only need one, as you’ll only wear it at night. 
  • Street Shoes: You’ll have time for excursions ashore when you dock. So, having a pair of closed shoes will be helpful as it’ll make walking around much easier. To avoid marking the boat deck, you should pack shoes with non-marking white soles. No, you don’t have to have boat shoes.
  • Flip Flops Or Sandals: They’ll be handy as you’ll spend a lot of time swimming, so close shoes will be impractical.
  • Hat/Cap: It’s hard to escape from the sun when you’re in the middle of the ocean. So having a hat is a good idea to keep the sun off your face. 

What To Pack For A Luxury Yacht Charter Vacation

Superyachts afford every luxury and have much more storage space than smaller vessels. This means you can pack in your hard suitcase and bring a few extra luxuries you’d have to leave behind if you’re on a smaller yacht.

While your basic clothing items can and should stay the same, you can bring a bit more, giving you more variety.

Furthermore, you should also pack some exercise clothes and a pair of sweatpants. There’ll be a gym on the bigger yachts that you can work out in, so you’ll need exercise gear.

Packing sweatpants might seem like a strange idea for a Caribbean holiday. But if you’re on a superyacht, you’ll have air-conditioning throughout the vessel.

The definition of luxury (Photo credit: Unsplash)

🏴‍☠️ Non-Clothing Essentials For A Crewed Caribbean Vacation

There are some essentials you’ll need for your crewed Caribbean sailing trip. These include:

Polarized Sunglasses

Sunglasses are essential on a boat. You’ll be outside a lot, and it’ll be very bright because of the reflection of the sun off the ocean. So, pack a pair of sunglasses because your eyes will thank you!

Water Bottle

You’ll spend tons of time in the sun, potentially leading to dehydration. The best way to avoid this is to have a water bottle with you so you’re always drinking water. 


Quick-drying beach towels are useful, and they’re small and lightweight.

Small Bag For Daytrips

When you’re exploring the island when you dock, it’ll be helpful to have a small bag with you. It’ll allow you to carry things like your towel, water bottle, and anything you might buy on shore. 


You’ll have to hop on a dinghy to get to shore from your boat, and in the process, you’ll get a bit wet. So, it’ll be helpful to have a small dry bag to keep your valuables, like your phone, safe and dry. 


You’ll likely need an adapter to charge your phone or tablet while on board. The type of adapter will vary between vessels. So, it’s best to speak to your charter company and find out what is needed. 

Goggles & A Snorkel

These will be a great addition to the trip, as there are many great places to snorkel in the Caribbean. But these may be provided by the boat or be available for hire. So chat with your charter company and see what the options are. 

🧴 Toiletries To Pack For A Crewed Caribbean Sailing Yacht Charter

There are some crucial things to remember when you’re packing toiletries for your Caribbean sailing trip. They should be travel-sized, so they don’t take up too much space.

They should also be environmentally friendly as they’ll end up in the ocean. While some yachts may offer toiletries, you will often be charged extra for them.

If you want to keep your holiday bill down, rather bring your own. 

Toiletries you should pack


You will spend tons of time in the sun. You’re on a yacht in the Caribbean, so you’ll be doing a lot of swimming and tanning. But the quickest way to ruin your holiday is to get badly sunburnt.

Some places, like the U.S. Virgin Islands, have banned sunblock containing certain chemicals. This is due to their harmful effect on coral reefs. So, make sure you do your research before you go or buy the reef-safe sunscreen upon arrival at your destination.

Insect repellent

Lip balm

Shampoo and soap

Toothbrush and toothpaste


Yachts aren’t a big space, so don’t let your fellow sailors smell you for the wrong reasons. 

Seasickness tablets

You never know when motion sickness can happen, so these might be handy.

A Portable Bluetooth speaker

You’re on holiday. Sit back and relax while enjoying your favorite tunes. 

Only pack the essentials for smaller sailing boats (Photo credit: Unsplash)

✖️ What Not To Pack For A Caribbean Crewed Sailing Trip

Now that I’ve established what you should include in your suitcase, it’s time to go through what you definitely don’t need to pack. This list will cover clothing (for everyone) and general items and applies to boats of all sizes. 

Clothing To Leave Behind


Denim should be left behind for several reasons. It takes up lots of space in your luggage and doesn’t dry quickly, which isn’t suitable for hot Caribbean weather. 

Formal Clothing

You’re on holiday, so leave the suit and tuxedo at home. You won’t need it at all. Formal clothing is like denim; it takes up a lot of space and isn’t particularly practical. You’ll need a nice shirt or summer dress, but nothing more formal than that.

High-Heeled Shoes

High-heeled shoes are impractical for navigating a yacht and for getting on and off it. They also damage the floors of the boats, so they should be left at home.

Wet Weather Gear

On the occasion it does rain, you’ll be able to stay dry in the boat’s cabin. As the ship is crewed, you won’t need to venture outside to operate the vessel, so you don’t need wet weather clothes.

Heavy Jackets

The Caribbean gets extremely hot. Even in winter, it is warm, doesn’t drop below 70 degrees Fahrenheit (21 C), and is usually warmer. A thick jacket is unnecessary in this kind of weather, so it’s best to leave it behind. 

General Items To Leave Behind

Expensive Jewelry

You’re on holiday in the Caribbean, meaning you’ll do lots of swimming and other fun activities. You don’t want your expensive jewelry to fall off when you’re in the water. Also bear in mind safety and petty crime in parts of the Caribbean. Instead, leave it behind and have fun with total peace of mind. 

Cooking Equipment

The boat you’re on will come with the necessary cooking equipment, no matter the size. As it is a crewed trip, the crew will also do all the cooking for you when you’re not eating out. 

Laptops & Other Large Electronics

Boats tend not to have a lot of space on them, so it’s best to avoid large electronic devices. You’re on holiday, so leave your laptop behind and unwind completely. Playing cards are a great substitute.

Large First Aid Kit

The boat you’re on will have a first aid kit, so you don’t need to bring this along. You can throw in some small plasters and other small general items that you might use more often, as these won’t take up much space. 

Excessive Amounts Of Makeup

This isn’t to say that you should leave all your makeup behind, but rather that you should only back the essentials. There isn’t a lot of space on board for you to bring a complete makeup set. You’ll also be swimming (and sweating) a lot, making a lot of makeup quite impractical. 

Leave non-essentials at home (Photo credit: Unsplash)

❓ FAQs

What Do You Wear On A Boat In The Caribbean?

You’ll spend most of your days in a bathing suit and light t-shirts, as you’ll constantly be in and out of the water.

You might want a shirt or dress to change into in the evenings. But it doesn’t need to be formal. The dress code is summer casual, so whatever you’re comfortable wearing in the hot weather will be perfect for the boat. 

What Should I Pack For A Week On A Yacht?

There are some things that should 100% be in your suitcase. These include sunblock, a hat, and a swimsuit.

You’ll want lightweight, loose clothing. It’s a sailing vacation in the Caribbean, so it’ll be very humid. You don’t need heavy jackets or anything like that. Sunglasses will also be handy, as there’ll be a lot of reflection from the sun off the water. 

🧳 Final Tips & Tricks

Pack light for your sailing trip because you’ll basically be living in your swimsuit. On the occasions you aren’t, I recommend bringing lightweight, quick-drying summer clothing.

Avoid thick winter clothes and use breathable materials like linen if you want something other than a t-shirt. 

Remember also to use common sense and do your research by speaking to the charter company or broker before you leave. They’ll know the boat’s specifications and will be able to tell you what you do and don’t need to bring, depending on the yacht. 

Now that you know what to include, it’s time to pack your bags and prepare for the holiday of a lifetime. If you still looking for some inspiration then browse these Caribbean sailing tours to help you decide.

I’m the founder and chief editor here at Sailing Savvy. I spent a decade working as a professional mariner and currently, I mix those experiences with digital publishing. Welcome, and I hope that we can be the hub you need for safe passage.