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How to Get Started Sailing

A view from the yacht's deck to the bow and sails, Baltic sea
Aleksey Stemmer/Shutterstock

Sailing might seem like an expensive hobby reserved for the super-rich and their friends but really if it’s something you want to do, getting started is probably easier than you think.

What Kind of Sailing Interests You?

There are two main kinds of recreational sailing: cruising and racing. You need to decide which interests you the most.

Cruising is (generally) relaxed sailing between different ports. If you’ve got a week, you might work your way through a chain of islands sailing all day and stopping somewhere different each night. For the most part, it’s pretty chill although covering longer distances can involve sailing non-stop—even at night—for days, or if you’re crossing an ocean, weeks.

Racing is exactly what it sounds like. A fleet of boats all set off at the same time and aim to be the first to finish the set course. People race everything from small one-person dinghies around a short course of buoys close to the shore to 100-foot catamarans around the world. Unless you get very serious, most races take a few hours on a weekend afternoon.

I’ve both cruised and raced, but when you’re starting, you’re likely to be drawn to one kind over the other. If you’re looking to enjoy the good life, sipping cocktails on a sunny deck, obviously it’s cruising you’re after. On the other hand, if you want a wet and wild ride, take to racing.

Take a Beginners Course

Sailing, once you get started, is surprisingly easy. It’s one of those things where you’ll get the basics down quite quickly but mastering it takes a lifetime. If you live near the coast or a large enough lake, there will almost certainly be a sailing school that does adult beginner courses during the summer—assuming you don’t have a friend who’s happy to teach you.

A couple learning to sail in Dye's Inlet, Silverdale, Washington
The Old Major/Shutterstock

There are two main options you’ll encounter for beginner courses: small boat courses and yacht courses.

In a small boat course, you’ll learn the basics in a classroom and sailing alone in a small dinghy. The instructors will be in powerboats to shout advice as needed. It’s probably the best way to learn how the wind affects sailboats because everything is so immediate. Expect to get wet when your boat capsizes (tips over on its side).

In a yacht course, an instructor takes you and your coursemates out on a larger yacht, often something around 30 foot. They’ll talk you through everything, direct you, and give you time at the helm. It’s useful if you’re only planning to sail on larger boats, but you won’t develop as good an understanding of the nuances of sailing.

We’d recommend taking a small boat course if possible. The experience you get from a few hours at the helm of a fast, nippy dinghy is invaluable. Then, if you plan on sailing yachts, try a one- or two-day intermediate course.

Join a Yacht or Dinghy Club

While this step is not essential, it can make it easier to find people to sail with. If there’s a nearby yacht or dinghy club, look into joining. Don’t bother with super-expensive prestigious yacht clubs. You’re looking for something cheap and cheerful that has regular events and a good few people.

If You Want to Start Cruising

Now that you know the basics of how to sail and won’t be useless on deck, it’s time to look for a boat to sail on.

The most important tip I have is to be available. Sailing bigger yachts requires a few crew members, so there are always yacht owners who need extra hands. The problem is they need extra hands when they want them, not when you’re thinking about going for a day sail. If you’re prepared to jump on board on short notice to help move a boat 100 miles down the coast, then you’re going to be welcome.

Similarly, yacht owners are typically inundated with friends looking to visit when the boat is in the Caribbean, but they don’t want to join for the two-week trek down from Maine. If you’re available to do the long passages, boat owners will be fighting to have you onboard. And of course, you’ll be able to stick around once the boat makes it to the tropics.

It’s no secret that sailing skews towards older men. Cruising isn’t especially physical, but it’s still useful to have someone younger and fitter around as needed. If you’re a bit younger or fitter than the average sailor, that’s going to count for you.

If you’re a member of a yacht club, start letting people know that you’re available to crew. You’ll soon find someone who needs a hand. You can also check out websites like FindACrew and Crewseekers. Look for local Facebook groups too.

If You Want to Start Racing

Sailing yacht race, regatta

If you want to start racing you have two options: buy your own boat or find a boat on which to crew.

Option 1: Buy a Boat

If you caught the small boat bug back when you were learning to sail, buying your own and racing it is the obvious next step. Check out what boats people race in your local club and start enquiring about used ones. You should be able to buy any of the standard single person dinghies for less than $2,000.

If you’re not quite ready to buy a boat yet, you can also ask about renting. If someone has one laid up in their garage, they might be willing to let you race it.

Option 2: Find a Boat to Crew

If you’re more interested in yacht racing, then things are even easier. Just go down to the yacht club whenever there’s a race on and ask around. Every club I’ve been to always has a pool of roving crew for people to grab from. There’s always a boat where a regular crew member couldn’t make it. Show that you’re reliable and you’ll quickly have a regular spot on a boat.

Sailing is great fun and, despite its image, it’s easy enough to get started. Get the basics down, and you’ll find that boat owners always need people to help out whether you want to cruise or race.

Harry Guinness Harry Guinness
Harry Guinness is a photography expert and writer with nearly a decade of experience. His work has been published in newspapers like the New York Times and on a variety of other websites, including Lifehacker. Read Full Bio »
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