A sailing trip in the Caribbean is a dream vacation for many—think azure waters, swaying palm trees, and the freedom to explore hidden coves and vibrant islands. Whether you’re a seasoned sailor or embarking on your first nautical adventure, understanding what to pack can make all the difference in ensuring a smooth and enjoyable experience. This listicle is designed to guide you through the essentials, with tips and tricks to help you pack efficiently and effectively for a week-long Caribbean sailing escapade.
And as necessary as what is ON your sailing trip packing list is what is NOT ON your sailing trip packing list. I will share all of those items, too.
⬇And I am here to help you avoid this situation (actual picture of my luggage).⬇
Affiliate Disclosure: There are affiliate links throughout this post. This means if you click on a link and purchase a product through that link, then I will receive a small commission for the referral. And that is kinda cool.
Sailing Trip Packing List: How to Pack for a One Week Sailing Adventure in the Caribbean.
The sailing trip packing list is mainly geared toward the ladies, as men pack very differently. My husband is good with two shirts, two pairs of shorts, maybe a guayabera, one rash guard, couple undies, flops, and boat shoes, and perhaps a cap. The rest will be up to me.
Before setting sail, ensure you have the necessary items for a comfortable and safe voyage. First, ensure your travel documents, such as your passport and any necessary visas, are up to date and secure.
A first-aid kit is another essential—it should include seasickness tablets, band-aids, and personal medications (I will go through First Aid Kit Essentials below). Also, remember a reusable water bottle to stay hydrated; dehydration can sneak up when you’re out on the open sea.
Let’s start with the luggage.
Space is at a premium on a sailboat, so packing efficiently is key. Use soft-sided luggage like a duffel bag or backpack, which can easily be stowed away. Consider using packing cubes to organize your belongings and save space. And remember, less is more — prioritize multi-functional items and leave room for any souvenirs you might pick up along the way.
After you unload everything and tuck it all away in drawers, you can then roll up the bag and store it quickly out of the way.
The Samsonite Duffel with wheels flattens out when empty and tucks under the bed or is easily stored away. The wheels help in transport (as my luggage tends to be heavy). Each family member has a Samsonite rolling duffel. We have used them for years, and they have remained sturdy and practical for all of our adventures.
You also need a dry bag to carry your camera equipment, phone, and wallet through the water to the shore.
Most of the time, there will be a dinghy dock. However, even travel by dinghy can get your stuff wet, so protect it with a dry bag. Occasionally, you will not have the luxury of a dinghy dock and will have to get to shore by swimming.
My favorite dry bag is the Overboard Waterproof Dry Tube Bag. It comes in several different sizes (5L, 12L, 20L, 30L, and 40L) and has an adjustable shoulder strap. We have a 12 L and a 20L, which is enough space for our family of four. There are hiking opportunities in the BVI, and these bags will double up for hiking adventures as well.
One more thing about bags: Bring several sizes of ziplock/plastic bags.
Ziplock bags can be used to carry cash, keep your wallet dry, or store a wet swimsuit in your duffel at the end of the trip. They are also useful in the kitchen. If you buy a bottle of Rum (you might), you can use a large ziplock bag to transport it back home safely.
Toiletries you will need on your sailing trip packing list.
Picture this…
Your day will consist of swimming and water sports, hiking, and seeing fantastic views. You will also casually hang out with friends and family on deck, eat and drink, and float around in the water. While on the islands, you will sweat and be covered in sunscreen and bug spray for a fair amount of time.
Your hair will be in various stages of wet, salty, dry, salty, in a cap, ponytail. Did I mention salty? What I am getting at is many things that you may use on a typical day at home you will not need on the sailboat.
DO NOT bring a blow dryer or a hair straightener.
This will not be happening on the boat!
You will need a good quality shampoo and conditioner and a great leave-in detangler/conditioner.
Use the Bumble and Bumble Surf Spray after towel drying your hair, then let the salty air be your blow dryer. The Surf Spray is oil and salt-infused, does not dry out my hair, and gives it that beachy look.
Advice for makeup users.
It is hot out there, and you will sweat. Foundation, blush, and powder will be washed off because you will be in and out of the water all week. Bring a waterproof mascara, if you must. I always bring lip balm with SPF and some tint, and that’s about it for makeup.
Add these items to your sailing trip packing list.
- Sunscreen with SPF 50. DO NOT bring the spray sunscreen because this will create a slippery deck and can damage the surface. Make sure you use sunscreen with protection against both UVB and UVA. UVA penetrates the skin deeper and causes skin aging (AKA wrinkles). UVA also contributes to the development of skin cancer. Use Sunscreen Lotion, biodegradable if possible, to protect the reefs. There are multiple reef-safe products on Amazon.com. I’m in love with Sun Bum Products.
- Bug Spray, I prefer DEET-free to do my part in protecting the reefs. My husband hates bugs, so he likes extra DEET (I’m only half kidding). My kids prefer wipes.
- after sun lotion with aloe
- deodorant
- toothbrush, toothpaste
- hairbrush
- hair ties
- *Razor*
*Some Razor advice*
On many sailboats, you will need to conserve water. You will be asked to take a “sailor shower.” A sailor shower goes like this: turn the shower on, get yourself wet, turn off the water, wash and shampoo, then turn the water back on to rinse.
It is challenging to fit shaving into this routine. It can be done, but it isn’t very pleasant. After our first experience on the water for a week, I had my entire legs and bikini area lasered—no more worries about that. I would advise waxing before the trip, at least in the bikini area. It will be one less thing to consume your precious time.
What to pack to wear.
Here is what happened.
The first time we sailed for ten days, I brought back half of my clothes unused. The second time we sailed for a week, I did a little better, although I still brought back about a quarter of my clothes unused.
You will be in a swimsuit and cover-up all day, mostly every day. Many days, I used two swimsuits. We would swim in the morning, freshen up before lunch, then put on a dry swimsuit. The wet one would be hung out to dry.
Ninja Tip: You don’t need to pack a lot of clothes.
Here is my list of clothes to add to your sailing trip packing list:
- 4 swimsuit cover-ups
- 2-3 rash guards
- 4 sport shorts/4 sport shirts (to be used for hiking and as a cover-up)
- 1-2 maxi dresses for evening dinner
- 3 cute shorts/3 tops to match (for lunch or dinner on the islands or exploring markets and/or boutiques)
- Maybe pack a romper (or two) if you are into rompers
- lightweight impermeable jacket as sometimes it rains
- 4 PJ’s/socks to sleep in if you wish
- underwear and bras for the week
- flip flops
- one pair of strappy sandals
- boat shoes or quick-drying tennis shoes
- water shoes (although quick-drying tennis shoes will work for this purpose as well)
- Don’t bring heels or wedges. Wear your flops or strappy sandals or go barefoot in the sand.
- costume jewelry (nothing too flashy or expensive)
- sunglasses (polarized) with neck strap
- cute hat/cap
- Bring heavy-duty clothespins for hanging swimsuits and towels to dry. Remember not to leave your clothes hanging too long—no one wants to see that, and it doesn’t look good in pictures!
- I waited until the last line to discuss the total number of swimsuits. Pack swimsuits last because they can be rolled and tucked all over the place in a duffel bag. I bring 6-8 suits. It is difficult for me to decide which ones to bring because I love them all. You will need sporty suits for paddle boarding, snorkeling, and kayaking. Some swimsuits will be for just hanging out on the island or in the sun. And you will need some photo-worthy suits. So, I bring lots.
Bring your pharmacy.
When traveling with the family, there is always some sort of ailment. Save time and stress by packing medications and ointments for every situation you can think of, especially with kids. For a Free Printable DIY First Aid Kit, check out THIS POST. Here are the basic items that I include.
- Motrin/Tylenol (pain relief/headaches)
- Imodium (diarrhea)
- Pepcid or Prilosec (heartburn)
- Pepto Bismol (GI upset)
- Sea bands, Dramamine, or Scopolamine patch (seasickness)
- Zofran (this is a prescription medication for nausea/seasickness)
- Allegra (allergies)
- Benadryl and EpiPen for our food-allergic daughter
- Benadryl ointment (rashes and bug bites)
- Cortisone ointment (rashes and bug bites)
- Basic first aid kit (Bandaids, gauze, tape, disinfectant wipes) You can also purchase a basic first aid kit from Amazon.com.
Seasickness will ruin your day, but it doesn’t have to.
My entire family experiences motion sickness; it is clearly genetic. Don’t let your fear of motion sickness keep you from experiencing the vacation of a lifetime. I devoted an entire post to how to prevent and treat seasickness. This post is full of my best tips.
Don’t let it happen to you!
Tech and Toys to add to your sailing trip packing list.
We travel with children so we need lots of stuff for safe exercise and entertainment. The boats often come equipped with watersports gear, but I still ensure all the following are included.
- kayak
- inflatable stand up paddleboard
- noodles for floating with a glass of champagne (the kids also use the noodles for snorkeling)
- goggles
- snorkel gear including fins
- waterproof camera with floaty (some need two floaties)
- Lifeproof cover for iPhone
- Bring your Canon EOS and protect it with your dry bag. The pictures are so worth the effort.
- Ipad (yes I allow some screen time for the kids)
- Each of us brings a book. The kids have some summer reading for school. Maybe I can talk them into it during our vacation. Doubtful!
- deck of cards
- “Uno” for the kids
- maybe a board game
- lots of chargers
- binoculars
- flashlight (this will be helpful at night when traveling by dinghy)
- Bluetooth speaker
- island playlist
- soft-sided cooler for the beach.
- personal water bottles labeled for each member of the family
- beach football
Bring a flag to help identify your boat, as they all tend to look alike.
Another ninja tip: Bring an extra flag to hang up at the Soggy Dollar Bar in White Bay.
Pack a sharp knife in your checked luggage.
We just returned from our week in the British Virgin Islands. There was a knife on the boat. Undoubtedly, it was the dullest knife known to man, and furthermore, there was no knife sharpener. Try peeling a mango or slicing a pretty red juicy tomato for a sandwich with a dull knife—it’s very annoying.
I used my pocket knife, which worked out okay. In light of this situation, add a sharp knife to your checklist and place it in your checked luggage.
Now, here is what NOT to add to your sailing trip packing list.
One of the biggest mistakes that first-time sailors make, including me, is packing too much.
Remember, you don’t need a lot of clothes. On a typical day, you will be in and out of the water, on the boat deck, on the beach, hiking, stand-up paddleboarding, kayaking, and snorkeling. You may also find yourself in a beach bar, drinking umbrella drinks and/or champagne.
Don’t pack too much, and don’t bring these items:
- hardback suitcase
- heels
- wedges
- blow dryer
- hair straightener
- spray sunscreen
- flashy, expensive jewelry
- lots of makeup
Final Tips and Reminders
I hope this sailing trip packing list is helpful and you have a fantastic adventure. With your bags packed, you’re ready for an unforgettable Caribbean sailing adventure. Double-check your list to ensure you haven’t forgotten any essentials, and don’t hesitate to personalize your packing based on your itinerary and planned activities. For those new to sailing, consider booking a call with a seasoned traveler or sailing expert to glean more tailored advice for your trip.
Bon voyage, and may your sails be filled with wind and your heart with adventure.
The British Virgin Islands are stunning. You will have adventure and relaxation and return home with amazing memories, a beautiful tan, and many pictures.
I can’t wait to hear all about it!
Click here for the printable two-page packing list for one week aboard a sailboat in the Caribbean.
These are my favorite things to do in the British Virgin Islands.
Here is a 7-day Soft Itinerary to help you plan your adventure in the British Virgin Islands.
I would be the one to forget my dry bag! That was a nice reminder. And Bumble and Bumble has some amazing hair products. HUGE fan!
I love those products, i have used them for years. They are extra great with tangles!!
Well, this was very interesting and I would think VERY helpful to new travelers. Well done. The next time I travel to the Caribbean on vacation, I shall use this list confidently.
Thank you, Jennifer.
Love,
Mom
Thanks, Mom!!
What a great list. I haven’t been sailing before but I’m a chronic overpacker and would have made so many mistakes. – Stephanie | http://www.theborrowedbabes.com
I am a chronic over packer, too. I need my lists…and most of the time, I still over pack. I keep trying.
It’s funny that both things, the blower and hair straighteners, you mentioned to not take on the trip are both things I did pa k to take on my first 3 trips. Now I don’t take them. Turns out I never used them while traveling.
I have done it before, too. Pack them and never remove them from my bag. I just leave them at home, it’s a vacation from all of that fluff, too!!
This is such a great guide! The ziplock bags are brilliant! We could of really used those on our last trip! This sounds so fun!
Thank you! They are so practical and easy to pack. We used them for all sorts of things. WE are headed out in a month, so excited!
Thanks for the complete list. The dry bags are a great find for me. Going to pin it for when I need it. 🙂
They are so useful. We did not have one the first trip and the captain let us borrow his. Since then, we bring a couple sizes!
What an exciting idea! I love to cruise but never would have thought to venture out on my own.
We’ve done this twice with a captain, so we think we are pros!! Ha Ha! We’ll see how it goes. The couple who we are going with are boat people. They are out 2-3 times a week, so between all of us, I think we will be ok. Also, The Moorings gives a three-four hour hands on tutorial before they let us take their boat. Wish me luck.
I have read very carefully your advice because although it has already been on a sailing boat I think that the experience of others is always useful and that’s why I took the opportunity to take notes.
Thank you for reading and commenting. I researched so much before we went both times, and still researching. I almost have it perfected! I made my own checklists tonight as we leave this week for the Caribbean. I am going to try to stick to the list this time.
Such a detailed post. I have never thought about going on a sail boat before but it does sounds like it can be fun. The whole turn on the shower get wet, turn off, soap and turn on to rinse thing sounds like a bit of a pain though. A wax would for sure be in order before the trip.
Seriously, the shower is a pain. Much better without the need to shave, though. When we returned, we all went to the shower in the spa. It had a rain shower and a regular shower that worked at the same time. I may have been in there for thirty minutes!! It is totally worth it. A trip of a lifetime.
Most charter boats have a fresh water shower hose and a swim platform on the stern. Go swimming, soap and shampoo on the swim platform in your bathing suit, rinse off in the ocean and briefly rinse off the salt water with the shower hose. No need to use those claustrophobic indoor showers and it saves on fresh water.
This is the best idea. Those sailor showers are rough.
Good List! Thanks for sharing!
Dry bags are such a sensible recommendation – and the Samsonite duffels (I’ve been meaning to get one for ages). I like to pack tiny natural sponges – they are great for sailor showers and somehow stay fresh no matter how you abuse them
The dry bags are the most useful thing that I pack. They are great. We have several different sizes and use them all. I never thought about the sponges, that it a great idea.
I hate packing – especially if I only travel with hand luggage. I’ve never packed for a sailboat tour though, but I think it would be hard for me as well, because I wouldn’t know what to pack. So your guide is so great and very informative. Thank you so much 🙂
I am a terrible packer and after all of that organization, my suitcase was still labeled as “HEAVY” at the airport! I keep trying.
I have never been sailing, but this is a great list to keep in mind when I go for it. You gave some great tips about the bags. And seriously, clothes are always excess wherever we go. I seem to bring back some of them unsused!
I always do. And my suitcase is almost always too heavy for the airlines. I keep trying.
This sounds like a great new vacation idea for me, very unique. Great post!
Thank you. We have gone for a few summers in a row. It is the best.
I overpack all the time haha! Would love travel again tho!
I still do, but I keep trying!
These is a useful guide for sailors, I would definitely consider these items If I was to sail. Thanks.
Very well informative post, full of small but invaluable tips! A great write up. Thanks a lot for sharing.
Thank you!
This sounds like such a great adventure- though I’m not sure I could handle my family in that tight of quarters for a whole week! We had a sailboat and spent time sailing around the San Juan Islands in the Puget Sound when I was a kid- but I haven’t been on a sailboat in a long time!
Funny you say that, and I totally get it! Yes, it can be a little tight at times!
I’m a fan of practical information, and you’ve hit that nail on the head. I always agonize over what to pack for even the simplest holiday, so your post is gold. Thinking about a sailing adventure… Thanks!
Go for it! I hope this list helps, and keeps your from the dreaded tariff on heavy luggage!
When I was young I used to do a lot of sailing & loved every minute of it… never went on such an extended trip like this, but it sounds like such fun. Thanks so much for sharing this list!
It is one of our favorite things to do. Hopefully, we will be back this summer.
Your blog has very useful tips for travelers! Am not an avid traveler, but I always learn a lot from your articles! Thanks.
Thank you, John. I learn tons from you, too.
I have never been on a sailboat or a cruise for more than a few hours. Maybe one day. I loved reading these tips and can be used for other trips also.
It is different, but so much fun!