What to Wear on a Sailing Trip.

What to Wear on a Sailing Trip

Written by Zuzana Prochazka
November 17, 2022

Last Updated on September 1, 2023 by Boatsetter Team

Going sailing for the first time and wondering what to wear? Time, place, type of sailing, and boat will necessitate different preparation.

Start with these questions: Are you sailing for an afternoon or a weekend? Will you be sailing in the tropics, like the Florida Keys, or someplace cooler, like the Northeast or the Pacific Northwest? What kind of sailboat– open or with a cabin?

Run through our checklist on what to wear when sailing for your upcoming boating trip:

  • Lifejacket (personal floatation device)
  • Footwear
  • Headwear
  • Outerwear
  • Foul weather & technical gear

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Lifejacket (Personal Floatation Device)

If you don’t swim, are on a small open boat, or sail through unfavorable weather conditions, you’ll need a personal floatation device (PFD). It’s always best to ask the boat owner where the lifejackets are stowed if they haven’t already gone over this with you. The law requires a vessel to carry a US Coast Guard-approved lifejacket for each person aboard.

PFDs can range from basic orange vests to high-tech inflatable PFDs, so ask what’s available and try them on because they’re not equally comfortable. Before departing the dock, check that the PFD fits properly, especially for kids!

Pro Boat Type Tip: Did you know that catamarans (multi-hulled sailboats with two parallel hulls of equal size) have surged in popularity? You’re likely to see these beautiful boats while on your excursion (if you aren’t already on one!)

Sailing Wearing Lifejackets (PFDs).


Sailing barefoot is tempting but not advised! Sailboat decks are slick and covered with toe-stubbing obstacles (which can be worse than stepping on legos!)

Choose slip-resistant, close-toed deck shoes with non-marking soles. It’s best not to assume all athletic shoes are safe, as boat owners don’t like scuff marks from dark soles. For offshore sailing or cold weather, you may need waterproof sailing boots with good tread, but for a breezy afternoon, flip-flops work (just watch those toes!)


No matter the weather, hats are our friends. It could be a baseball cap, a wide-brimmed hat, a wooly cap, or a beanie. You want to keep your scalp from burning, the sun off your face, and stay warm. Jackets with hoods help in cold weather, but they’re not enough on their own.

Pro Sailing Tips: Don’t forget a hat clip! More hats go overboard when sailing than during any other boating trip.

Sailing Wearing Jacket and Hat.


This depends on a couple of factors. A swimsuit, t-shirt, and shorts are fine for a summer day sail. It is still best to bring a light jacket on hot days (for the windchill). Light nylon shirts with long sleeves and rash guards dry quickly and are also good for sun protection. This is key because you won’t feel the effects of the sun as you sail in a breeze.

Wind and waterproof jackets work well when it’s cold. Avoid heavy cotton sweatshirts because once wet, those stay wet and will chill you to the bone via evaporative cooling. Most importantly, put on layers! Carry options and choose bright colors that make you visible on deck or in the water should you find yourself there accidentally.


Make sure to protect your hands with sailing gloves! Lines on small boats are thin and can cause rope burns. Save your hands with gloves that can be long or short-fingered and usually have padding on the palm and a quick-drying mesh on the back to keep your hands dry and comfortable.

Don’t underestimate how cold a metal steering wheel can be or how chapped your hands will get in the wind. If you’re out in the cold, then you should pack heavy gloves beyond the sailing version. Not all kinds of sailing require gloves, so ask your host if they’ll be needed.

Foul Weather and Technical Gear

If you’re going out for a serious, long, or offshore sail, you’ll need top gear. Foul weather gear and waterproof garments will save the day. Foulies usually include a heavy-duty jacket and bib overalls. High-quality foulies are not cheap, so it might be best to borrow this gear from a good boater friend.

Sailing Foulies.

Sunscreen, Sunglasses, & Lights

On the water, you will have to wrestle with the sun. Protect your eyes with full-coverage polarized sunglasses. Attach them with a lanyard and bring more than one pair (especially if they’re prescription) just in case they go flying.

Sunscreen is a must, even on cloudy days. If you’re extra susceptible to burning, wear a buff with sunglasses and a hat for near-full head protection. Don’t forget the lip balm.

A headlamp will be handy if you’re maneuvering around a sailboat in the dark and need to keep your hands free. A light with a red and white light option is best to protect your night vision.

If you don’t know, ask

Your host will be more than happy to describe the kind of sailing you’ll be doing and what you’ll need. Ask and think through your wardrobe and accessories. Pack everything into a soft-sided backpack or duffel that won’t damage the boat and can be stowed in small places.

Bring all that you think you may need to be safe and comfortable. Here’s our last Pro Sailing Tip: Make a list of what you think you’ll need and share it with your host for helpful feedback. Go out and have a blast!

Learn more about boating types, gear, and fun water toys at Boating Resources.

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