Table of Contents

17 Top Sailing Packing List Items for 2022 + What to Wear & NOT to Bring

17 Top Sailing Packing List Items for 2022 + What to Wear & NOT to Bring
Updated on

There’s a way to travel almost anywhere on the planet without having to haul along a suitcase, pay for flights and hotels or wait around in lines. People who travel this way get to explore for years and take their home along with them. They aren’t restricted by roads or international borders, and they get direct access to the world’s most beautiful islands and beaches by harnessing the power of the wind and currents. All you need is a sailboat and the wind.

If this sounds appealing to you, then maybe a sailing passage is a good option for your next vacation. If you are new to sailing and don’t know what gear you’ll need to bring to the high seas, we’ve got you covered. Below is a packing list of essential items to bring on any sailing trip with links to Amazon for your convenience, plus info on what NOT to bring or wear.

What to Pack for a Sailing Trip - 17 Essentials

  • 1. Neck Wallet

    You probably won’t need to worry about your valuables while out on the high seas, but this neck wallet is perfect for ports of call along the way. The truth is that many popular sailing destinations have high levels of poverty, which means you could encounter a pickpocket. With the HERO Neck Wallet, you can keep your cash, credit cards, passport, keys, and other valuables safely hidden away inside your clothing.

  • 2. Garmin InReach

    On a sailboat, you will often find yourself beyond the range of cell and internet service. In order to keep in touch with friends and family, you’ll need to use some kind of satellite communication. The Garmin InReach is the satellite messenger of choice for sailors and adventurers. With this small handheld unit, you can send and receive texts, navigate, receive weather info, track your position, send an SOS signal, and more.

  • 3. Packing Cubes

    On a sailboat, every inch of space must be utilized and safety gear always takes priority over clothing. In order to fit your sailing clothes into the smallest possible space, you’ll want to use packing cubes. These HERO Packing Cubes come in a set of five different sizes to stow all of your clothes, plus they come with two free laundry bags.

  • 4. Sleeping Bag

    Even in moderate latitudes, it can get quite cold at night on the water, especially if there is a strong wind blowing. At sea, I end up sleeping in a proper sleeping bag nine out of ten nights, especially if I choose to nap in the cockpit. The TETON Sports LEEF 20F+ sleeping bag is cozy, comfortable, reasonably priced, and more than adequate to keep you warm throughout the sailing season in most boating destinations.

  • 5. Quick-dry Travel Towel

    It should be no surprise that on a sailing trip, one can expect to get wet often. Whether that is due to jumping over the side for a swim in the Caribbean or getting hit by a rogue wave, you’ll always be happy you brought the HERO Microfiber Quick Dry Towel for drying off. This towel takes up almost no space and dries itself in minutes, unlike a regular towel.

  • 6. Headlamp

    One of the first items that I pack before any sailing trip is my headlamp. On a sailboat, you’ll need both your hands for hanging on, steering the vessel, and working the lines, so a headlamp is absolutely essential for sailing after dark. I love the GEARLIGHT S 500 LED because it lasts for ages without needing a new battery, and it has the red light function to save your night vision.

  • 7. Cooling Towel

    One towel is rarely enough on any boating trip, and I like to pair my HERO Quick Dry Travel Towel with the HERO Cooling Towel. This one comes in a two-pack and is the perfect size for drying off after a quick swim or washing the salt off my face after a long stint at the helm.

  • 8. Waterproof Duffel Bag

    On a long sailing trip, it’s best to assume that everything you bring will get wet at one point, especially if you plan to sail offshore. In order to keep your gear dry, you’ll want to pack things away in a proper dry bag. I brought the Earth Pak Waterproof Voyager Duffel on my last crossing to Hawaii, and it kept my gear bone dry the entire voyage.

  • 9. Hanging Toiletry Bag

    Whenever I go on a sailing trip, I like to keep all my toiletries together in one place. I found that this hanging toiletry bag functions perfectly for this purpose, with just enough space for my toothbrush, toothpaste, razor, shaver, deodorant, and shower supplies. The hook is perfect for hanging it up from the yacht club shower room or the onboard head.

  • 10. Inflatable Life Jacket

    This is an extremely important one. It goes without saying that each crew member needs to be prepared to survive in case they fall overboard, but unfortunately few sailors choose to wear a bulky life vest unless it’s an emergency. This inflatable vest solves the problem since you’ll barely remember you’re wearing it until you fall in and it automatically inflates.

  • 11. Floating Wrist Strap

    Until I started using this floating wrist strap, I can’t tell you how many valuable items I’ve lost to Davy Jones’s Locker. But that all stopped once I purchased a few of these floating straps to attach to my keys, camera, and other easy-to-drop items. Now if I drop something into the water all I have to do is turn the boat around and scoop it back up.

  • 12. Lifestraw Water Bottle

    In many popular sailing destinations, the drinking water can be of questionable quality, or even unsafe to drink. But sometimes there is no alternative except to fill up with water from the marina. That’s why I always bring my Lifestraw Water Bottle, which filters out 99.9% of dirt and dangerous bacteria. Just remember to only use it with fresh water.

  • 13. Universal Waterproof Phone Case

    There are few things more frustrating than pulling out your phone to capture the perfect sunset shot, only to have an unexpected wave soak your device with water. Fortunately, there is an easy way to prevent your phone from suffering water damage. Simply keep your phone in a JOTO Universal Waterproof Phone Case whenever you are on the boat and you’ll be safe – even if it falls in the drink!

  • 14. EPIRB

    This is one of those things that you hope to never need, but should always bring just in case. In 30 years of sailing, I have only used an EPIRB once, but I was very glad I had it. The ACR ResQLink 400 is small enough to fit in your pocket, but it could save your life if an emergency comes up offshore.

  • 15. Travel Insurance

    Like an EPIRB, travel insurance is another thing that you hope to never need, but if you do it could make all the difference. In many ways, sailing is safer than driving to work, but there are certain risks that cannot be eliminated. Protect yourself and your traveling companions with a travel insurance policy. It doesn’t cost that much but could save you tens of thousands of dollars in an emergency. We like to use TravelInsurance.com to compare policies from top companies and find the one that’s best for us.

  • 16. Daypack

    For me, one of the greatest pleasures on a sailing adventure is leaving the boat in port and exploring the surrounding areas on foot. For that, you’ll need a daypack that is light and comfortable but roomy enough to store all the essentials for an all-day adventure. I found the TETON Sports Oasis 18L perfect for day hikes, plus it comes with a free hydration system.

  • 17. Portable Charger

    When it’s my turn to watch the helm, I like to bring my phone to listen to music or an audiobook. But before I discovered this handy portable charger, I would often find myself stuck with a dead battery halfway through the night watch. Now I always keep this charger in my sailing jacket pocket, and I haven’t had a dead cell phone battery in years.

What to Wear on a Sailing Trip


What should you wear while sailing? That depends on where you go and the conditions that you can expect to encounter. The most important thing is to be prepared for anything because once you leave the dock, there are no clothing stores at sea.

If you plan to sail in the tropics, most of the time you’ll want to dress for sun protection and to keep cool. I like to wear shorts or a swimsuit, along with a short sleeve shirt, sunhat and glasses and plenty of sunscreen. In colder climates, start with a warm base layer, add insulation as needed, and cover up with a waterproof set of foul weather gear.


What Should WOMEN Wear on a Sailing Trip? – (Click to expand)

Below is a sample women’s clothing list. (All items link to Amazon.com for your convenience).

On a sailing voyage, women should wear clothes that are comfortable, durable, and keep out the wind and water. The most important thing is to dress to stay warm and dry at all times (unless it’s hot and you are planning on getting wet intentionally, of course). Many sailing routes will expose you to a wide variety of weather conditions, which means you’ll need to be prepared for anything from extreme heat to stormy weather with strong winds and breaking waves. The most important clothing item for any sailor is their set of foul weather gear, so choose a high-quality set. Don’t forget to bring plenty of layers so that you can change out your clothes to suit the current conditions.

What Should MEN Wear on a Sailing Trip? – (Click to expand)

Below is a sample men’s clothing list. (All items link to Amazon.com for your convenience).

On a sailing voyage, men should dress for comfort, that way they can remain on deck for long periods of time without getting too wet or cold. On the ocean, the weather can change in minutes, and a squall can quickly turn a beautiful day into a storm. That’s why it’s important to layer up, starting with a warm base layer and working up to your foul weather gear, which is your primary protection from the elements. On hot days, wear your shorts or swimsuit, but keep your waterproof clothing close by just in case.

Dressing for the Seasons

SPRING – March, April, May


People tend to picture sailors as always lying on the beach in a swimsuit with a coconut in one hand and a bottle of rum in the other. But depending on where you sail, you could encounter anything from hurricanes to icebergs. Most of our readers sail out of North America, so we will focus on typical weather conditions there.

In the spring, sailors can expect a good deal of rain and squally weather as the season shifts towards summer. Make sure to bring a good wind/rainproof jacket and a solid pair of waterproof boots. Take a few extra sweaters to wear under your foul weather gear on cool days, but don’t forget your sun protection for warmer days.


SUMMER – June, July, August

In the summer, you’ll want to dress to protect yourself from the sun reflecting off the water. Put on plenty of sunscreen and don’t forget to wear your sunhat and glasses. On warm days, wear shorts or a swimsuit, as well as an activewear shirt that can easily dry once wet. For your feet, wear sandals or go barefoot.

On the ocean, foul weather can hit any time of year, even at the height of summer. Don’t forget to bring your foul weather gear and waterproof boots in case rough weather comes up. It’s better to have it and not need it than the other way around.

FALL – September, October, November


Fall, like spring, is a time of changing weather patterns on the ocean. Oftentimes, the worst storms of the year hit not in the middle of winter but during the fall (or spring) equinox. So if you plan to sail in late fall, be ready for some potential extreme weather.

That said, fall can be a time of great beauty on the water and many areas experience a pleasant “Indian summer” through September and well into October. That’s why in the fall you’ll want to pack everything from your sunglasses to your drysuit, with plenty of layers for insulation. If the weather is cool but not quite bad enough for foul weather gear, wear waterproof pants and a windbreaker.


WINTER – December, January, February

Sailing in the wintertime is reserved for a hardy breed known as “frostbite sailors”. 95% of boat owners who live in temperate climates pack away their boats for the winter. But those who brave the storms and freezing temperatures may be rewarded with empty anchorages, Robinson-Crusoe-style islands, and winter bonfires on lonely beaches. For some, it’s the best time of year to sail.

If you plan to sail in the winter, make sure you are dressed for it. Start with a warm base layer and insulate with sweaters, a down jacket, and fleece pants. Cover up with offshore foul weather gear and protect your extremities with waterproof gloves and sailing boots.

Dressing Appropriately for the Activity – (Click to expand)

Coastal Sailing:

On the coast, you’ll often be able to sail in short hops and wait out rough weather in port. Since you can choose the best times for sailing, you’ll be able to take advantage of nice weather. Wear jeans and a nautical sweater, as well as a sunhat and glasses. Sandals work well as deck shoes, or you can go barefoot. Don’t forget to wear your inflatable life vest at all times underway.

Offshore Passages:

At sea, you are exposed to the best and the worst that the ocean can throw at you. It’s up to your skills and endurance to make the most of the conditions. Keep yourself warm and dry with a high quality set of foul weather gear, and wear plenty of layers underneath when it’s cold. If the sky is clear, use proper sun protection, and always remember to stay connected to the boat with a safety harness.

Exploring Ports of Call:

Half of the voyage is getting there but the other half is exploring the places you sail to. With the boat securely moored, you can take a day excursion ashore. Wear comfortable walking pants and an activewear shirt. Even if it’s warm, don’t forget to put a sweater and raincoat in your daypack and wear comfortable walking shoes.

What NOT to Bring on a Sailing Trip

  • 1.DON’T Bring Jet Skis or Noisy Generators

    People sail to get away from the noise and pollution. If you respect the ocean and the animals (and humans) who call it home, keep the noise down and bring a paddleboard or kayak instead.

  • 2.DON’T Bring Too Much Cash

    At sea, there are no restaurants, hotels or casinos to blow your money, so too much cash is likely to just get lost or destroyed. Instead, bring a book or a musical instrument and enjoy the solitude.

  • 3.DON’T Bring Delicate Items

    The ocean is a harsh place and delicate items are unlikely to survive long at sea. It’s best to bring only the most durable items on a long sea voyage and leave things that are likely to break back home.

  • 4.DON’T Bring a Schedule

    The sea can ruin the most well-thought-out plans and Poseidon laughs at those with a pre-planned itinerary. At sea you must learn to be flexible, so leave your daily planner ashore.

  • 5.DON’T Bring Guns

    International laws make it almost impossible to sail to different countries with firearms. If you get in a dangerous situation, a gun will likely make it worse. Bring your guns on a hunting trip, not sailing.

  • 6.DON’T Bring a Pirate Flag

    The novelty of pirate flags has long since worn out in the sailing community. Don’t be like the guy on the broken down boat at the end of the marina. Be creative and find an interesting flag to fly.

What NOT to Wear on a Sailing Trip – (Click to expand)

On a sailing trip, you’ll need to be able to move around freely, so don’t wear super tight clothing. Instead, bring loose-fitting but comfortable clothes that allow full freedom of movement. Definitely don’t wear Sperry Topsiders sailing shoes, which can be used to identify people who have never left the dock. And finally, don’t wear a Captain Jack Sparrow outfit on a serious sailing voyage if you are over eight years of age.

FAQs About Sailing Voyages

  • 1. Do you need a Captain’s license to sail a boat?

    In the United States (and most countries around the world) you don’t need a captain’s license in order to skipper a boat. Unlike a car, anyone can legally steer a recreational vessel if they own it or have permission from the owner. If you plan to sail professionally with passengers or as a paid captain, you will need to obtain your captain’s license.

    Do you need a Captain’s license to sail a boat?
  • 2. What should I do if I get seasick?

    Seasickness is common on sailboats, especially if you sail offshore or in rough weather. Fortunately, 99% of people get over it in a few days, even if the conditions remain rough. Some people choose to take Dramamine or crew ginger candies to help their bodies adjust to the motion.

  • 3. How can I get the necessary experience?

    It takes many years to gain the necessary experience to sail your own boat offshore. You can begin by reading books and articles about sailing and offering to crew for friends with boats. Even sailing a small dinghy helps you learn the basic fundamentals of sailing. Many boat owners will offer lessons in exchange for helping with boat work and repairs.

    How can I get the necessary experience?
  • 4. Should I expect to encounter a storm?

    If you sail coastally in the right seasons, there is little reason to get caught out in a storm. Modern forecasting tools make it possible for any professional captain to take advantage of safe weather windows and avoid storms. Offshore, when you sometimes sail for weeks or months between ports, it’s often impossible to avoid dangerous weather, and you must be prepared to deploy storm sailing tactics.

  • 5. What are the dangers involved with sailing?

    Like anything on the ocean, sailing is not without risk. At sea, you can suffer from equipment failure, a medical emergency, storms, calms, collision with debris or ice, pirates, or various other dangers. Fortunately, an experienced captain who carefully prepares for each voyage can eliminate 95% of that risk. The last 5% is left to skill and luck.

    What are the dangers involved with sailing?
  • 6. How far should I sail each day?

    If you plan to make short coastal passages on a medium-sized cruising sailboat (30-45 feet), you should have no problem sailing 20-30 miles each day. Offshore, when you are sailing 24 hours a day, most boats can average between 100 and 150 miles per day. Smaller boats tend to sail slower, and some racing sailboats are capable of covering more than 500 miles in a day.

  • 7. Should I sail a small or large boat?

    New boaters tend to aim for the larger boat right from the start, thinking that a bigger boat is faster and more comfortable. But the reality is that a large boat is much more difficult to handle and costs far more to operate. Unless you can hire your own captain, it’s best for beginning sailors to start with the smallest boat that they can live on comfortably.

    Should I sail a small or large boat?
  • 8. How do you sleep on a long sailing passage?

    This is one of my most frequently asked questions. No, sailors cannot anchor in the middle of the ocean to sleep at night. Boats use self steering systems like electric autopilots or windvanes to steer 24 hours a day, and the crew set a watch schedule so that someone is always keeping a lookout. Solo sailors nap for a few minutes at a time in between checking on the boat.

  • 9. How much does it cost to go on a sailing trip?

    Your budget depends entirely on your lifestyle, size and type of boat, and where you plan to sail. Some sailors on large yachts can easily blow tens of thousands of dollars in a single night. On the other end of the spectrum, I have sailed happily for over a month and spent less than $100. Most full time cruisers spend between $1500 and $5000 a month on expenses.

    How much does it cost to go on a sailing trip?