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What To Wear Sailing On A Small Sailboat 2022 Helpful Guide

A friend invited you sailing or you have decided to learn to sail and are headed out for the first time. You will be going out on a small 14-19 foot 1 or 2 person sailboat. What should you wear?  You want to stay comfortable and be not too hot, not too cold, and not feeling like a soggy sponge all day.  Your clothing choice can make or break your first day sailing. If you are planning on going sailing on a small sailboat or dinghy you’ll wear very different clothing than on a 40 foot sailing yacht. You want to know what to wear sailing on a small sailboat.

Are you sailing on a small sailboat or big sailboat

So you’re going to go sailing and want to know what you should wear out on a sailboat? The first thing to ask is how big is the sailboat because wardrobe requirements are drastically different. Are you going to go out on a Hobie Cat, Lightning, or Sunfish or one of the many small sailboats out there, or are you going out on your friends 30 foot cruising boat? If you’re going out on a small boat, probably less than 20 feet without a keel your in the right place.

See the below video for some information on small boat sailing and examples of small sailboats or dinghies.

What to wear sailing on a small sailboat

If you are going out on a small sailboat you should plan to get wet. If there is wind, capsize is a real possibility. Even if you don’t capsize your close enough to the water that you are going to get sprayed as your boat crashes through waves. All your clothes should be items that are comfortable when wet and also quick drying. See the below video for a quick guide on what to wear sailing on a small sailboat.

Now we’ll get to the specifics of what items you should wear and bring with you when you head out sailing the first time.

Bathing suit

Bathing suits are great to wear sailing on a small sailboat. They are perfect for getting wet. If it’s a nice warm day and the water temperature isn’t too cold that’s all you really need. Maybe a quick drying shirt and shorts to go with it.

Technical Shirt, Quick Drying Shirt or Rashguard

Rashguards are made of lycra/spandex and are quick drying, comfortable when wet and most are also protect you from UV. They make great shirts to wear while sailing small sailboats. Any other synthetic quick drying shirt will work great too. Cotton isn’t great because once it gets wet it doesn’t dry that quick. It loses all insulating value once it’s wet also. Cotton is a great material to wear if you want to feel soggy cold and wet.

Gill Mens UV Tec Zip Neck Top

  • MOISTURE-WICKING FABRIC – The UV Tec Zip Tee is made from ultra lightweight pique fabric that actively wicks moisture away from the skin.
  • 50+ UV PROTECTION – The UV protection built into the fabric to protect you against the harmful effects of the sun’s rays and allows you to get on with the job on board.
  • FLAT LOCKED SEAMS – This lightweight fishing shirt features flat locked seams for superb comfort, preventing rub or chafing.

Technical Shorts, Quick Drying shorts

Whatever you wear on your bottom is going to get wet. Something that is quick drying and not soggy is good. For guys bathing suits are excellent. For woman you may want to wear running shorts or something else synthetic and quick drying on top of your bathing suit. Tights are popular these days as well.

Gill Men’s Expedition Shorts

  • Quick drying
  • Low profile Velcro adjustment on waist
  • 2 deep thigh pockets
  • Zippered thigh pocket for secure storage
  • 50+ UV Protection: Lightweight, cool and comfortable nylon fabric with durable water repellent finish

Water shoes Or Dinghy Boots

Small sailboats will collect water in the bottom where your feet go. You will more than likely always be standing in a puddle. There are also a ton of metal objects in the boat that you can cut your feet on. Many boats have metal bailers with sharp edges. You should never go barefoot sailing unless you look down in the boat and there really is nothing sharp and metal in there. Hiking boots that are made for small boat sailing are great. Any water shore or sandal that isn’t open toed will work good.

GILL Men’s Waterproof Lace Up Rubber Edge Boots

  • Rubber sole
  • Always striving to provide the best possible sailing gear, we work with sailors to design for sailors, ensuring you get accessories which are built around your needs.
  • New for 2018, our Gill Edge Boots are both secure and flexible for optimised performance.
  • Lace closure system for improved fit
  • Wide supportive ankle strap for support. High grip sole. Reinforced heel, toe and bridge area for increased support

Life jacket (no inflatables)

The next most important thing is a comfortable PFD or life jacket. When sailing on a small boat the chances are good that sooner or later you’ll end up in the water. Even if you don’t capsize the boat, you may fall out. I once had a crew fall out of my Lightning because my knot holding the hiking strap to the boat came undone.

Inflatable life jackets should not be worn on small sailboats. They can get caught in the rigging when they inflate trapping you under a capsized boat. This happened at a regatta I was at on Lake Erie a few years ago and resulted in a drowning. Inflatables are good for big sailboats where no one regularly goes in the water and the boat isn’t capsizing.

For more information on PFDs, see my guide to dinghy sailing PFDs.

Gill USCG Approved Side Zip PFD

  • US Coast Guard Approved
  • Side zip opening for ease of use
  • Ladder lock adjustment for a secure fit
  • Adjustable shoulder length with neoprene padding
  • Front zippered pocket with mesh drainage

Sailing Gloves

When sailing on small boats most of the time your holding onto the ropes. If it’s windy you rarely ever want to cleat ropes off. Sailing gloves protect your hands from getting rope burn. They are similar to weight lifting gloves or batting gloves or any other gloves that have a leather palm and finger surface. Your hands will thank you after a day of pulling in and hanging onto ropes.

Gill Men’s 7242 Short Finger Champion Sailing Glove

  • Offset finger seams to remove pressure points and reduce wear
  • Pre-shaped construction fits your natural hand shape
  • Wide neoprene wrist band with stretch
  • Wraparound palm protection eliminates uncomfortable side seams. Inside facing wrist closure prevents accidental starting of watch. Dura-grip fabric on palm construction providing incredible levels of grip. Improved abrasion resistance and grip

Baseball cap

It’s nice to have a little protection from the sun out on a sailboat. The standard baseball cap tends to work best on small sailboats. There is a lot of rigging and ropes hanging around and they are all good at grabbing hats off your head and tossing them in the water.

Bigger sun hats tend to get caught by the boom and other rigging easily. A small sailboat is not the place to wear a big fancy sun hat if you want to keep it.

See my guide to sailing hats for more information.

Gill Race Cap

  • Hook and Loop closure
  • FEATURES: Wicking inner headband Clear front for team branding 50+ UV protection Retainer cord with clip
  • Technology: 50+ UV protection. Lightweight water resistant fabric.

In addition to boat rigging knocking hats off, the wind can do a pretty good job of it also. You should get a hat leash or strap to attach your hat to the rest of your clothes. Chinstrap built into a hat don’t do a great job because a big gust of wind from behind you will easily still blow the hat forward off your head.

Croakies Lid Latches

  • Croakies’ lid latch clips your hat to your collar with a strong metal bulldog clip giving your hat security on a windy day
  • Made of durable woven Climbing rope
  • Measures 10 inches long
  • Made in the USA

Spray top

Spray tops are non-insulated shell jackets with a tight seal around your neck, wrists and waist. They are great for blocking the wind a spray. High performance sailing dinghies that plane or foil can create a fire hose level of spray onto you. They are good to wear on windy days when there will be lots of spray. A generic rain jacket will work okay as long as it isn’t so sloppy fitting that water can easily go up your back. You should be careful that the hood won’t catch on anything while you or the sails are moving around.

Gill Mens Pro Top

  • Gill have taken the Pro Top to the next level this season, optimising the design with a new close fitting PU neck and side zip for even better water resistance when sailing.
  • Two layers of breathable material keep excess moisture away from the body whilst an adjustable waistband and cuffs help to expel water at every angle.
  • Close fitting PU neck seal for for a watertight seal
  • Adjustable Neoprene waistband for a secure and watertight seal. 2-layer coated fabric with a durable repellent finish. Fully taped seams for a waterproof seal. Fabric Composition. 100% Nylon
  • Adjustable PU cuffs for watertight comfort

Spray pants

Waterproof pants that will block the wind and spray from your legs. Waterproof is essential. Breathable material is really good so that you don’t get spongy underneath from moisture build up.

Gill Men’s Pilot Waterproof Inshore Sailing Trousers

  • WATERPROOF SAILING PANTS – The Gill Pilot Trousers have been carefully crafted using a polyester outer layer with nylon lining to help with waterproofing and warmth whilst inshore sailing.
  • ALL-YEAR ROUND TROUSERS – Designed to be worn alone, or as an outer layer in colder weather, these versatile trousers can be used all year round.
  • ELASTICATED WAISTBAND -These fully lined pants have an elasticated waistband with drawcord adjustment for improved fit.
  • POCKETS & CLOSURES – The Pilot trousers feature side pockets with external drainage to remove any excess water; adjustable ankle closures to reduce water ingress.


If it’s cooler out and the water temperature isn’t warm you may want to consider a wetsuit. A wetsuit is made of neoprene and insulate you while you are in the water.

When is it too cold to sail small sailboats without a wetsuit?  A good rule of thumb is the 120 degree rule.  If the water temperature plus the air temperature is below 120 degrees F you need to wear a wetsuit. 

For example.  If the air temperature is 75F degrees and the water temperature is 65 degrees, the combined temperature is 140F and you do not need to wear a wetsuit. 

If the air temperature is 65F degrees and the water temperature is 50F degrees, the combined temperature is 115F degrees.  115F is less than 120F so you need to wear a wetsuit.

Synergy Triathlon Wetsuit 5/3mm – Men’s Endorphin Sleeveless Long John

  • SUITABLE FOR ALL LEVELS – Ironman & USAT approved. Athlete endorsed. Comes in wide range of sizes to ensure a perfect fit.
  • PROVEN TECHNOLOGY EQUALS SUPERIOR PERFORMANCE – Hydrodynamic neoprene made from Yamamoto #39 with SCS silicone coated SyPrene. 5mm thick core buoyancy panel / 3mm lower legs and back.
  • EXCEPTIONAL FUNCTIONALITY – Full range of motion. Unsurpassed 680 percent flexibility. Highest grade anti corrode internal wetsuit zipper from YKK which greatly reduces drag as you move through the water. Super soft low neck with smoothskin on both sides and because it is so soft, it feels like you hardly have anything around your neck.


A drysuit is a full body suit that is sealed at your neck, wrists and ankles so that no water can enter. You then layer up underneath it similar to how you would dress for skiing or any other winter outdoor activity. A drysuit is good once the combined air and water temperature is below 100 degrees F.

With a drysuit on, you can jump in the water and go swimming and be perfectly comfortable when there is snow on the ground and skim ice on the water.

For more information see my guide to wetsuits vs drysuits for sailing.

Stohlquist Ez Drysuit

  • Zipper closure
  • 4 Layer Twin Sensor Waterproof/Breathable Fabric: Nylon Shell Fabric with DWR Finish, Hydrophobic/Microporous Coating, Laminated Membrane, Nylon tricot lining
  • Super Stretch Neoprene Neck Gasket. MasterSeal waterproof cross-chest entry and relief zippers. Cordura reinforced seat and knees with mesh drainers
  • Fabric drysocks are universally sized.

launching laser sailboat

What to bring with you on a small sailboat

A small gear bag (drybag)

A small bag to put your other what to bring with you items. Space is at a premium on many small sailboats. Depending on how long you are going to be on the water you may leave this in your car or somewhere else on the shore. A waterproof dry bag is good for carrying anything that can’t get wet.

Earth Pak -Waterproof Dry Bag – Roll Top Dry Sack

  • RELIABLE PROTECTION: We believe our earth pak dry bags are the best out there–bar none. These dry bags are meant to last for years and provide waterproof protection for even the most rugged users.
  • SHOULDER STRAP: 10L & 20L dry bags come with a 24-42 Inch single shoulder strap. 30L, 40L, and 55L waterproof backpacks are equipped with backpack style shoulder straps that also come with a sternum strap for added stability.
  • IDEAL FOR TRAVEL: Our water bag is very lightweight and compact making it an essential dry bag for all your travel plans. Easy to fold and pack tight in any sized luggage!


Even if it’s cloudy you can still get sunburnt out on a boat. The water reflects the sunlight back at you giving you another opportunity to get burnt. The American Academy of Dermatology recommends the following:

  • Broad-spectrum protection (protects against UVA and UVB rays)
  • SPF 30 or higher
  • Water resistance

For more information on sunscreen click here.

Banana Boat Ultra Sport Reef Friendly Sunscreen Spray

  • Water resistant up to 80 minutes
  • Invisible clear spray
  • Easy grip spray can
  • Twist and lock spray, no cap
  • Twin Pack

Sunglasses (with a strap if you want to keep them)

A good set of polarized sunglasses will help protect your eyes from being damaged by the sun. If you really like your sunglasses a strap is a good idea to keep them attached to you. Like everything else that goes out on a small sailboat, they are easily knocked off your head into the water. The more expensive the sunglasses, the easier it seems to they to end up at the bottom of the lake.

KastKing Hiwassee Polarized Sport Sunglasses

  • Grilamid® frame
  • Made from superior German and Japanese raw materials 1.00mm thick polarized lens
  • Polarized
  • Scratch Resistant Coating coating
  • Lens width: 2.5 inches
  • KEY FEATURES – Polarized lenses reduce glare – Impact resistant TAC lenses protect your eyes from flying objects – Lightweight, durable, and comfortable Grilamid frames – Anti-slip nose and temple pads – Block 100% of the harmful UVA and UVB rays


You’ll get thirsty on the boat if your out for a long time. A water bottle with fresh water is a good idea or some other beverage. I’m not a huge fan of beer while small boating. Other people are. If you’re going out on a friend’s sailboat for the first time, you should check with them what their favorite on water and after water beverage is.


A granola bar or trail mix or other small snack is good if you’re going to be out a while. Keep in mind how messy the food you are bringing is. No one wants to scrape food gunk out of the bottom of their boat. Some food items are more or less prohibited from ever being out on any boat. Cheetos or yellow cheesy puffs are the biggest offense you can possibly bring on a boat. They melt and turn into a super slippery slimy mess and they also stain the fiberglass gelcoat. Bananas are considered bad luck on boats just in case you had some urge to bring some with you.

A rigging knife or multitool

It’s a good idea to have a knife or multitool attached to your PFD or life jacket. You never really know when your going to have to cut something loose on a boat. Rigging knives are pocket knives with a few specialized tools for sailing. They have a marlin spike and a shackle tool. The marlin spike is exactly what it sounds like, a big spike. It is used for undoing knots. You work the spike into a knot and to loosen it up. A shackle tool is a slotted tool for opening shackles. Both come in really handy on a sailboat.

Maxam Sailor’s Tool

  • A DYNAMIC NAUTICAL KNIFE: The Maxam Sailor’s Tool is a powerfully-effective multi-sailing, -fishing, -camping and -hunting tool that’s designed for fast/easy cutting access and is efficiently packed in a sleek ruggedly compact stainless-steel body.
  • THE PERFECT ECONOMY SAILING KNIFE: Featuring a honed blade, marlinspike, shackle key, bottle opener and stainless-steel handle with a 2″-ruler on one side, 5-cm on the other, our functional sailor’s knife measures 6.125″ long when opened and 3.75″ closed.
  • A PRACTICAL RIGGING KNIFE: With a durably robust marlinspike running along the spine and a lanyard ring for secure storage, our affordable sailor’s tool can easily be utilized to pick lines as well as loosen all kinds of difficult-to-untie knots.


The Coast Guard requires every boat operating in US waters to have a sound producing device on board. Yelling loudly isn’t considered an acceptable method. Having a whistle attached to your PFD is a good idea for being able to signal someone if you fall in the water. It can be difficult to hear on a windy day with the wind and water noise overpowering everything. A whistle might save your day sometime. For more information on Coast Guard required equipment click here.

Storm Alert Whistle

  • The Storm All-Weather Safety Whistle – The Loudest Whistle On The Market
  • Patented Design Allows Whistle To Be Heard Up To 50 Feet Underwater
  • Unique Sounding Chamber Forces Out All Water When The Whistle Is Blown
  • A Great Self-Defense Program for Students or Anyone
  • Easy to Hold – Incredibly Loud


Your probably going to get wet while your out on the boat so drying off can be nice when you get back to shore.

Change of clothes

When your day of sailing is over, it’s nice to change into something dry. Bring an extra set of clothes so you can change and don’t need to drive home wet.


Boats are expensive. Trailering a boat of any size anywhere is expensive. If that boat is stored at a yacht club or marina those are really expensive. A little tip at the end of the day to the owner of the boat your sailing on is always nice. They may not accept it but the offer is always appreciated.

Go Have Fun Sailing

I hope you have a great day learning to sail or just going sailing. I find it a lot of fun and I hope you will too.

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About the author

My name is Doug Ryan. I am an outdoors enthusiast always looking forward to my next adventure. I spend as much time skiing, biking, and paddleboarding as I can. I decided to start Endless Rush Outdoors as a way to share my knowledge and enthusiasm for all things outdoor adventures and to help other people have as much fun as me.

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