SIGN UP & Enjoy

10% off

Join our newsletter to get 10% off with your first online purchase.
BONUS: Get a free Isy B. Beach Vacation Style Guide & printable packing checklist.

Look fabulous on the beach!
Sailing Trip Checklist: What to Wear on a Sailboat (+PDF)

Sailing Trip Checklist: What to Wear on a Sailboat (+PDF)

Ahoy there! Looking for the perfect sailing trip checklist to help you navigate through planning your Caribbean sailing holiday? This is our quick guide to packing your sailing trip essentials, a packing list to make sure you are ship shape and ready for anything when you board that beautiful Caribbean sailing yacht!

What to bring for a stylish sailing trip?

Despite the fact that you’ll be on the water, this is no time to let those standards slip darling! Of course, your main concern is to be comfortable and stay safe, but being stylish and put-together doesn’t hurt either. Whether spending lazy days lounging onboard, swimming in the beautiful crystal clear coves, or wandering through colorful Caribbean markets when you come into port, you’ll be well-prepared with our stylish sailing trip checklist. With the right clothing and accessories, you can effortlessly navigate your upcoming sailing trip like a pro.

Here are the Isy B.’s essentials that you should consider for your next boat trip packing list: 


Quick-dry, moisture-wicking tops and pants

Even if there are unexpected splashes or rain during your trip, these fabrics will keep you comfortable and dry. Look for tops and bottoms made from nylon, polyester, and spandex. A beautiful sun protective rash guard will keep you stylish and protected while enjoying the sun, sea, sand and waves. Where can you find a stylish rash guard that compliments your curves? 

The Mekaya rash guard is designed with a smooth body, slim fit and comfortable long-sleeves that keep the UV rays away with SPF 40. 

mekaya rash guard

Lightweight, long-sleeve cover-up

These are great for sun protection and can also be layered for cooler evenings on the deck. Opt for a light, breathable fabric such as linen or cotton. For example, bring a luxurious kimono style cover up to finish any look beautifully and stay warm on the chilly days on the water.

The Una's wish kimono is an elegant silk and cotton cover-up with a button closure to keep the wind away while being extremely light and delicate.

una's wish kimono

Waterproof jacket or rain gear

Rain gear and water-resistant clothing are necessities for any sailing trip. They will not only keep you dry in the event of an unexpected heavy rain, but they will also add an extra layer of warmth in case of chilly or windy conditions. An option to consider is a rain poncho, which can be a more lightweight and compact option than a waterproof jacket and pants. It can also be useful in case of a sudden shower, and it can be worn over your regular clothes without taking up too much space in your sailing trip luggage. 


Pack a swimsuit or two for taking a dip in the ocean or for lounging on deck. As the luggage that can be brought on a boat is quite limited and we know that you want to take a lot of pictures while on your trip, we suggest you grab a reversible bikini. This way you will be able to style the different sides of the swimsuit and create two completely different looks with only 1 pair of bikini. We promise, we won’t share your small secret! 

But where can you find a Caribbean inspired reversible bikini? Isy B.’s reversible bikini gives you the fun of two bikinis in one, and the freedom of changing your look according to your needs. On one side is the colorful dance print and the other side is a beautiful aqua blue, so have fun accessorizing your swimwear in multiple ways. How many combinations will you create?

dance reversible bikini set



Should you bring a dress onboard? Will you really need one on a sailboat? We say Yes. It’s even better when it's a dress that can work as a cover up or your go-to day-to-night dress. Choosing a dress that is comfortable, simple to move in, and won't get wet quickly is vital when preparing for a sailing trip. Look for a dress made of lightweight, breathable fabrics such as cotton or linen that will keep you cool and comfortable on hot days. Sundresses with sleeves also generally work better than strapless or spaghetti dresses as they provide more coverage and protection from sunburn. 

Check out the Adara kaftan dress made out of 100% luxurious rayon that is breathable and suitable for warm weather. 

adara kaftan dress

Sun hat 

When choosing a sun hat for a sailing trip, look for one made of a lightweight fabric that can keep you cool and comfortable on hot and sunny days. Also, look for a sun hat with a wide brim (at least 4 inches), as it will provide more coverage for your face, ears and neck. A hat with a tie or a chin strap, will keep your hat in place while on the boat and prevent it from flying away when the wind is up, and one that’s easily portable. We’re big fans of the iconic Tilley hats.


A pair of polarized sunglasses with a retainer strap is a necessity for a sailing trip as they will protect your eyes from glare. They also add a stylish touch to your outfit, and can be an important part of your protective gear when sailing. These Oakley Clifden sunglasses are polarized and designed with side shields to provide protection from the sun, wind and spray. They can also be customised to fit you.

Comfortable deck shoes or water shoes

These will provide good grip on a slippery deck and keep your feet protected from any sharp or hot surfaces. In terms of style, you can’t go wrong with the classic boat shoes from Sperry

A bag 

You’ll need a multi-tasking bag to carry all your essentials and to keep your valuables dry. Choose a bag for your sailing trip made of strong, quick-drying fabrics like nylon, polyester or canvas. Additionally, it should be big enough to fit all of your necessities without being too big to carry around on the deck and on-shore. Heading to the beach?

The Butterfly beach bag is chic, vibrant and fun, and folds up small to fit into your luggage but is also big enough to be a perfect carry-on bag too. 

butterfly beach tote bag


Is there a sailing dress code?

Although there isn't a set formal dress code for sailing, it is advised to wear proper clothing that is both comfortable and can be weather appropriate as it can be an unpredictable and dynamic environment. Your main objective is to be comfortable, safe, dry and protected from the elements. Your sailing dress code should include quick-drying, moisture-wicking tops and bottoms, light long sleeve tops, waterproof jackets or other rain gear, swimwear, sun hats, and comfortable deck shoes or water shoes. 

What to wear sailing in cold weather?

When sailing in cold weather, it's important to dress in layers to stay warm and comfortable. You should consider wearing at least 3 layers of clothing to keep you warm even if you get wet. You can remove them later if it gets too hot.  Make sure to protect your head, neck and hands from the cold wind with a warm hat, a neck gaiter and gloves. If it gets really cold, insulated and waterproof boots will protect your feet from the cold, wet and windy conditions. 


What to wear sailing in summer?

You’ll need gear that will keep you cool, comfortable, and sun protected when sailing in the summer. For example, lightweight and breathable tops and pants will help keep you cool and comfortable even in hot weather. Additionally, look for clothing with built-in sun protection such as UPF (Ultraviolet Protection Factor) or SPF (Sun Protection Factor). Overall, light-colored clothing is preferable as it reflects the sun's rays and keeps you cool. Don’t forget to bring a sun hat and polarized sunglasses that will protect your face and eyes from the sun, and also serve you as a stylish accessory. Bring a swimsuit so you may relax on the deck or take a dip in the ocean. It's also important to remember to stay hydrated and to bring along a water bottle. Also, make sure to pack a couple of bottles of sunscreen with SPF 30 or higher to protect your skin from sunburn.


Sailing Trip Checklist (PDF)

Download the Isy B.’s stylish Sailing Trip Checklist and get ready for your dream sailing holiday. 

 sailing trip checklist

With all that being said, and even though weather changes can be unpredictable on the water, don’t forget to check the weather forecast with your Captain or sailing company before you leave and let that guide your packing. With the appropriate clothing and accessories you can comfortably and stylishly enjoy your sailing vacation knowing that you are ready for any adventure.

Subscribe now for Isy B.’s newsletter for more style tips, inspiring content and discounts on your shopping.

Join our newsletter to get 10% off with your first online purchase.

BONUS: Get a free Isy B. Beach Vacation Style Guide & printable packing checklist to look fabulous on the beach.