Perfect Packing List for Newbie Sailors: What to Wear Sailing

Sailing is an amazingly unique way to explore the world and get away from it all. But packing for a sailing trip can be tricky. What should you wear sailing? What should you bring with you on a small sailboat? Hint: As light and flexible as possible.

Having helped crew a sailboat in BVI, I wanted to share my packing mistakes during my Caribbean sailing experience and what you should bring and leave at home.

As someone who has experience working at REI and loves outdoor gear, I hope this packing list will help you prepare for your sailing adventure. The list is geared towards short-term voyages but provides useful tips for longer trips as well. We’ll guide you on what to wear sailing and what items to bring to maximize your limited space.

Sailing Packing List: Have the Right Gear

Before you set sail on the high seas, you must ensure you have the right gear. The nearest shopping mall or Amazon pick-up locker may be an ferry ride, island chain and oceans away. You want to make sure you pack enough clothes and equipment to keep you comfortable, but not too much that it leaves your below deck messy. Keep in mind that when sailing, space is limited, so pack light!

What It’s Really Like on a Sailboat: Things to Consider

Pack for Where You’re Going

First, where you are going will vastly change what you wear sailing. Sailing for a week in warm weather Caribbean is going to look a lot different than if you are doing a transatlantic journey or winding your way around the colder temperatures like the Fjords of Norway.

For this post, I will mainly focus on a more beginner-friendly sailing destination like the Caribbean, where the temperature fluctuations are relatively constant.

Important Clothing Characteristics

• Quick-Dry: You are constantly moist and salty
• Lightweight & Breathable: It gets hot under the sun, but you don’t want to get sunburnt
• Easy to Clean: Sunscreen, sweat, and dirt are inescapable on a sailboat
• Simple: You’re going to destroy anything fancy
• Weather Protection (Cold and the Sun): Good gear can make your trip so much more comfortable

I hope I haven’t scared you away from sailing yet!

What to Wear Sailing: Everyday Clothing

Pack for your locale’s average highs and lows and prepare accordingly. When it comes to clothing for sailing, my top recommendation is to opt for layering instead of bringing one oversized and bulky item.

Everyday Clothing for Sailing (focused on warmer weather)

• Sufficient Number of T-Shirts and Shorts – It is hard to stay dry on a boat, and things get dirty, sunscreen, salt water, and sweaty fast.
• Quick-drying, technical shirt – Focus on technical clothing that is water-wicking, quick-drying, and breathable but also protects you from the sun’s rays. Many times these technical shirts offer odor-reducing properties as well.
• Lightweight, long pants and long sleeve shirt – good for UV protection and protection from potential chill while sailing. Even if it’s warm outside, the apparent wind can be chilly when you’re cruising along and getting sprayed by the sea (or drenched in the rain).
• Bathing Suit or Two

What to Wear Sailing: The Essentials

Foul Weather Gear

There is no way you aren’t going to get rained on a bunch, anywhere in the world, so wet weather gear may be the single most crucial gear to consider. Storms come and go and can develop rapidly at any moment, especially out at sea. Expect bad weather conditions at some point, and expect to need to work through it.

A great waterproof jacket usually also acts as a windbreaker. You’ll want to bring a heavy-duty rainjacket with windproofing qualities over the $5 plastic ponchos from the convenience store. Aside from the occasional windy day, a sailboat has plenty of places to snag your clothing, so a durable outer layer is essential.

Waterproof Rainjacket

Hear me out, as a petite female, I use this small men’s Arc’teryx rain jacket for a looser fit for all my layers underneath. Arc’teryx is $$$, but it is also the most one of the best rain jackets on the market that is not too bulky. I have used it since 2017 and occasionally maintain it with a waterproofing technical wash. I bring this gear with me anywhere.

However, if you’re looking for a rainjacket specific for sailing, Helly Hansen is one of the most well-known and best sailing brands worldwide. Aside from a lower price point than Arc’teryx, this jack is waterproof, windproof, and breathable to protect you against the harshest of weather.

▷SHOP: Helly Hansen Hooded Sailing Jacket

Waterproof Rain Pants

Waterproof trousers are another vital piece of sailing gear, especially if you are in cold weather. A good rain jacket matters more, but a good pair of rain pants is still a nice-to-have to keep you toasty when needed.

I have been using Mountain Hardwear’s Ozonic Rain Pants for years, and I love its waterproof and lightweight features. Test it yourself when you get your pants! Put it under the faucet as it is so satisfying to watch the beads roll right off.

▷SHOP: Women’s RainPants

▷SHOP: Men’s RainPants

Deck Shoes

If you’re sailing around the sunny Caribbean, you’ll see most people bare feet on board. But when temperatures drop, or choppy weather comes, you will want appropriate deck shoes.

Optimal boat shoes will give you grip, not scuff up the boat, and keep your feet protected and warm in colder climates. Although any type of shoes or sandals could be used, Sperry’s founder created the brand after literally falling overboard while sailing.

▷SHOP: Sperry Deck Shoes

Warm Sweater or Thermal Layer

Cold winds, water sprays, and damp environments make it challenging to maintain a comfortable temperature. The solution? Layer up. Bulky layers can be restrictive, hindering your ability to move freely and perform essential tasks on board.

I love using Smartwool’s thermal base layers as they use 100% high-quality merino wool to create the perfect balance between warmth, comfort, and durability. Wool fabrics usually make my skin itch, but somehow Smartwool’s clothing doesn’t at all!

▷SHOP: Women’s Base 250

▷SHOP: Men’s Base 250

Rashguard

Why are rashguards so important for sailing? First and foremost, they provide protection from harmful UV rays. When you’re out on the water for hours on end, your skin is exposed to intense sun exposure, which can lead to painful sunburns and long-term damage.

A rashguard acts as a shield, blocking harmful UVA and UVB rays from penetrating your skin, so you can enjoy your sailing experience without worrying about the sun’s harmful effects.

After day one of sailing without protection, we all resembled lobsters fresh out of the pot. Lesson learned – never underestimate the power of a good rashguard and hat combo.

▷SHOP: Women’s O’Neill Rashguard

▷SHOP: MEn’s Quicksilver Rashguard

Best Sailor’s Luggage Bag

Although not exactly something you wear, the right luggage is essential to a perfect sailing packing list. Leave your wheeled suitcases at home, and opt for a:

• Backpacking bag
• Duffle bag-style luggage
• Or at least a soft-case luggage

Picture your bedroom closet. Now, imagine it’s been shrunk down to the size of a toy chest. That’s basically what you’re dealing with when it comes to packing for a sailboat. Even if you have plenty of storage space at home, boats are notorious for being cramped and oddly-shaped. And sorry to break it to you, but those hardshell suitcases that you love so much? They’re not going to cut it on a sailboat.

I’m a big believer in purchasing items for multi-use, so my backpacking bag worked perfectly on a sailing excursion. A good quality backpack is an investment worth making, and your back will thank you later.

Here’s a little secret – no matter how big or small your backpack is, you’ll eventually fill it up. That’s why it’s best to choose a smaller bag than you think you need. Personally, I like to stick to bags that are 65L or less, but you should adjust according to your own minimalism abilities.

The more space you have, the more you’ll be tempted to stuff in unnecessary items that you won’t actually need. And let’s be real – nobody wants to lug around a heavy, overstuffed bag on a sailing adventure.

Best Adventure Packs

Not only is Osprey the perfect pack for your land adventures, but it’s also relevant for all you sailors out there. With its durable and water-resistant material, you can trust that your gear stays dry and safe during your sailing expeditions.

As my first backpacking bag, I personally stand behind Osprey, which lasted me for five years only because it was stolen. Its ergonomic design ensures you’re comfortable no matter how long your journey is. Plus, with its multiple compartments and pockets, everything you need is easily accessible.

But don’t just take my word for it; millions of adventurers sport Osprey as their trusted companion on the path.

▷SHOP: Women’s 65L Aura

▷SHOP: Men’s 65L Atmos

What to Wear Sailing: Accessories

⇨ Hat for sun protection – If you have a hat or baseball cap that you love and it doesn’t have a strap, don’t wear it while sailing. It gets windy on a sailboat; strap-ons are the way to go.

⇨ Unbreakable sunglasses with strap (polarized lenses) – There is no better time to invest in polarized lenses than out at sea. Polarized lenses cut out much of the sun’s glare and allow you to better see the water’s color and reefs. I buy these awesome-looking steampunk polarized lenses like 5 times a year mainly because although, not unbreakable, I lose them all the time, and they look awesome.

▷SHOP: Strapped Sunglasses

▷SHOP: Steampunk Sunglasses

⇨ Beach towel – Your charter company may provide towels, but you should bring your own for beaching purposes. Plus, it’s nice just to have a backup while sailing. I always bring an odor-reducing, quick-drying microfiber towel instead of a full-sized one.

⇨ Sailing Gloves – If you haven’t trained your callouses enough, get sailing gloves to avoid the rope burn. Sailing gloves allow you to maintain a good grip and come in half-finger and full-length.

Other Sailing Packing Essentials

⇨ Reef Safe, Waterproof Sunscreen – You would be surprised how often sunscreen is forgotten. Well, after your first hot sunny day, you will remember. Intense sun coupled with ray reflections off the sails, sea, and hull from all directions equals a bad sunburn, no matter how tough you think you are. Due to the strong UV rays, use a higher sun protection factor than you think you need. 

Note: For the protection of the reefs, try to purchase reef-safe sunscreen.

⇨ Prescription Medications – Most places and countries have access to decent pharmacies. Still, your prescription medications may be difficult to replace if you forget to bring them.

⇨ Sea sickness medication – Dramamine is a good choice, but if you’ve never tried it, I suggest taking it before sailing to test side effects. Some people get super drowsy, others can get headaches. There is a less drowsy and non-drowsy option available. Ginger pills can be a good alternative.

⇨ Insect repellent – Another obvious, but often overlooked item is insect repellent. I love the natural lemon grass or eucalyptus insect repellants, which aren’t as harsh-smelling as the super-strong DEET ones. Other options include Picaridin which comes in many different varieties, even as a pre-spray for your clothes.

⇨ Baby Powder – You may be wondering about this one. I can attest to this miracle-in-bottle form for any humid, wet places you may journey to. Baby powder sucks the moisture right out of your skin, leaving you smooth and dry when you go to bed.

⇨ Chapstick! – Your lips get so dry from the wind and the salt.

⇨ Snorkel Gear – Many charter companies provide fins, masks, and snorkels, but it may be nice to bring your own mask at least. A bit chunk of your sailing adventures will be swimming around coral reefs and checking out the local marine life. Masks with a tint tend not to fog up as much as clear ones.

⇨ Wetsuit & Dry Suits– A wet suit is not necessary anywhere in the Caribbean. But, if you are going somewhere with a cooler water temperature, you may want to bring a wetsuit or dry suit to stay comfortable.

⇨ Waterproof Dry Bag – Keeping things dry on a boat is a monumental task. Bring a durable dry sail bag with you for mini-adventures with the dinghy or to swim to shore with.

Sea to Summit is a great, trustworthy brand that offers different-sized dry bags, lighterweight dry sacks, or opt for a waterproof backpack.

⇨ Strong Flashlight or Headlamp – After dinner and trying to navigate your dinghy out of the channel back to your sailboat? Be prepared by carrying a light with you.

Best Headlamps for Lumen Value: Black Diamond Storm 400 
Traditional flashlight (lightweight and waterproof): Flashlight by Genwiss can even be used as a night dive or snorkel light.

Electronics to Pack

⇨ Camera, Battery, enough SD Cards – I never leave home without my camera gear. I always have my Sony A6400 Mirrorless camera, a great lightweight traveling camera.

⇨ GoPro – If there is ever a chance to engage in water activities, I always bring an action cam to capture the excitement. You never know when you will encounter a turtle or a giant school of barracuda.

⇨ Travel Adapter (location dependent)

⇨ High mAH Power Bank – Recommended: 20,000 mAH Anker Portable Charger

Other Important Things to Add to the Sailing Packing Checklist

• Passport
• COVID-19 Requirements (If Any)
• Visa Requirements (If Any)
• Plastic Bags or Ziplock Bags
• Aftersun or Aloe Vera Cream
• Basic Toiletries

✘ Hiking Shoes – This highly depends on where you will go, but my river shoes were more than heavy-duty enough for any on-land excursions. Plus, any other type of real shoes risks getting wet and never drying.

✘ Make-Up – Trust me on this one; the constant moist and salty air will undo all the make-up you do anyway.

✘ Nice Things You Don’t Want to Lose – Most beach clubs and restaurants accept casual attire for clothing. With that said, it is nice to bring one nice outfit for that special occasion.

In terms of jewelry or other fancy accessories, it is incredibly easy to lose things in the nooks and crannies in boats. When you can’t find something, you always have to wonder, “Did it fall overboard?” the moment you can’t find something.

Final Thoughts: What to wear and Bring Sailing

What to wear sailing and what to bring for a perfect sailing trip looks different for each traveler. If you are a passenger versus crewing, warm or cold weather, season of sail, many factors change what is deemed essential. 

Most days, you’ll be in your bikini or swim shorts enjoying the day, so as long as you are prepared for the elements, you’ll be ready to have the time of your life!