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DIVEIN’s guide to: 

Getting into Sailing

Our experts at work

We gave our Sea lovers one job:

Produce a guide for everybody who wants to get into sailing.

torben lonne

William Porter

Author
William moved onto his sailboat and has been cruising around the world since 2012.

bradley axmith author

Bradley Axmith

Boating Editor at DIVEIN.com
Vikingship building gear enthusiast and waterworld fanatic.

So a friend took you out for a sail, and you caught the sailing bug? How can you learn more? Should you go get a boat of your own? And when can you get out there again?

Some people have seawater in their blood from an early age. Parents who sail bring their kids into the sport. The kids are immediately comfortable and gain a love of water and sailing. But many don’t come from boating families and don’t get on a sailboat until later in life.

The good news is, it’s never too late to learn to sail. Many think sailing requires a lot of money, and they start after they’ve begun to earn a little more income. But that’s not necessary for adults.

Young sailor on the yacht working with rope on the winch

There are many ways to get on the water without waiting for your boat-owning friends to invite. And when you know you’re ready, you can get your own boat and sail as much as you want, where and when you want.

Types of Sailing

How you sail and what you like affects everything, from how you learn to sail to the type of boat you buy. You don’t have to pick one type of sailing. Just because you love the thrill of racing doesn’t mean you can’t take your boat out and spend a weekend on an island offshore.

Sailboats on a sunset

But when you’re learning, it’s good to know what you can expect. Racing dinghies or keelboats is a very different experience from cruising from quiet anchorage to quiet anchorage.

Racing

It’s said that any time there are two boats in sight of each other, a race is on. Seeing a boat gaining on you is an inspiration to check your trim and tighten up your boat, but there is a formal sport of sailboat racing, which is quite popular. 

At its most common level – the club race – boats go out on a weeknight or weekend and chase each other around a set of marks. Like you see in golf, there’s a handicapping system to adjust finish times for different boats, so faster and slower boats can compete against each other.

The four sailing boats on windward buoy racing

There are also fleets of identical “one-design” boats, and many weekend and multi-day regattas with a much higher level of competition. Sailors race everything from the smallest dinghies designed for children on short courses up to massive multi-million dollar custom yachts crewed by professionals in offshore distance races across oceans.

Most beginning sailors don’t jump straight to racing, but club racing fleets welcome even the newest sailors since there’s always a boat with space and everyone wants to bring new sailors to the sport.

Cruising

“Cruising” a sailboat is just a fancy word for taking your boat someplace away from your slip or mooring for a longer duration. Similar to racing, you can cruise a lot of different ways, but the most common cruiser is the weekend and vacation sailor. 

Every weekend, dedicated sailors get on their boats and sail away from their home port to somewhere different. It can be the next harbor down the bay, an island not too far offshore, a multi-week vacation adventure, or a full season far from home.

A Super Yacht Berthed in Gibraltar

On the other end of the cruising spectrum are full-time liveaboards and blue water cruisers. These sailors live on their boats and sail from country to country, spending years abroad and following global weather patterns, like the trade winds, for crossing oceans.

You don’t need a big boat to cruise, you just need a desire to head somewhere different. Larger boats have living facilities to meet your basic needs, and the larger the boat, the more plush and comfortable your time onboard will be.

Day Sailing

Getting out on the water with no particular place to go is a popular pastime, especially with small boat owners, though you can and should day sail anything. A dinghy or small boat designed for day sails doesn’t have accommodation down below, but they’re easy to set up and put away. 

Young people driving motorboats summer lake

Popping out after work or for a few hours on a weekend is very manageable. Most don’t have keels and are easy to get in and out of the water, and can store on trailers or dollies instead of more expensive mooring or slips.

Day sailers are great starter and learning boats before you take the plunge on something bigger. 

Types of Boats

If you’re thinking about buying a boat, consider what you want to do with the boat. But even if you make a determination like “I want to cruise, and I will never race”, there are still thousands of boats and styles to choose from. Whether you’re on the water or walking the docks, you’ll have questions!

Dinghies and Day Sailing

There’s no hard and fast rule about what a sailing “dinghy” is, but most boats considered a dinghy are small, have no living space or space below decks, and don’t have a fixed ballast (weight on the bottom for stability). These are great boats for day sailing, and racing dinghies is popular. There are big fleets, and the boats aren’t expensive or difficult to rig and sail with one or two people.

Popular racing dinghies include the Laser, the 420, 470 and 505, and a RS Aero. Some favorite day sailers include the slightly bigger Flying Scot and the Wayfarer. The Sunfish is another, more sporty dinghy worth looking at for its ease of use and maintenance.

If there are enough daysailers of the same type in an area, a racing fleet will inevitably develop.

Monohulls & Keel Boats

The monohull is the boat most think of if you ask them to draw a sailboat. There is a single hull and an underwater stabilizer – whether a centerboard, daggerboard, or keel. 

Underwater boat keel

A keel may be thousands of pounds of lead or other dense material, but it gives the stiffness and resistance to tipping when heeling over and the push back against the wind that the boat needs to sail.

Some advantages of single hulled boats are lower build cost, the ability to right when tipped over, loading and weight affects them less, and they sail closer to the wind. But they do heel (tip), and some find that uncomfortable or frightening, they are heavier, and are often not as fast as multihulls.

There are hundreds of brands of monohulls to choose from new and used. They will be anywhere from 18 feet to more than 50, but some of the more common coastal cruising production boats you’ll see are made by Beneteau, Jeanneau, Hanse, Hunter, Bavaria and Catalina. 

Sailboats at sea

On the higher end, Hallberg-Rassy, Hinckley, Swan, and Oyster are a few of the premium offshore brands. Popular racing boats include Farr, Melges, J/Boats, X-Yachts.

Almost all these designers and builders make boats that overlap functions, so you will have race boats with livable interiors and cruising boats with enough zip under sail to be fun and competitive to race. The Beneteau First series is a good example of a cruiser/racer, as well as many offerings from J-Boats and X-Yachts.

Multi-hulls: Catamarans and Trimarans

Over the last two decades, catamarans have grown in popularity among boat owners because they afford a level of space and comfort beyond that of traditional sailboats, and sailing them is more comfortable. First and foremost, catamarans are wider and therefore provide roomier decks and indoor eating spaces.

It’s tough for a monohull to compare with the living space in a bridge deck saloon or the aft cockpit areas of larger catamarans, and the hulls give ample space for cabins and sleeping. 

Sailing upwind, a catamaran stays flat and doesn’t tip, giving an easier ride.

Dark night view on sailing boat anchored on open sea with black silhouette of island

Many small, day-sailing versions of cats and tris are easy to sail, a lot of fun, and you’ll see them at many resorts throughout the world. Some of those will tip if you aren’t careful! But they’re also sporty and easy to rise up again.

Catamarans have two identical hulls, but a Trimaran has a single central hull and two smaller outside hulls or “amas.” The amas aren’t living spaces, but can act as storage for items like kayaks. 

A tri-hull sailboat is anchored off a sunny beach.

Because the trimaran needs a narrow center hull, they have no more space than monohulls. But they are light, incredibly fast, and draw next to no water so you can anchor them almost up on a beach.

But catamarans aren’t without disadvantages. With two hulls and a bridge deck connecting them, catamarans are more expensive to build and buy. Because they’re wider too, a slip in a marina is both more expensive and harder to find as a guest.

Overloading also hurts multi-hull performance, so capacity for gear and supplies is limited. Any rough sea state that pounds the bridge deck can be quite uncomfortable. 

And while big catamarans are very difficult to capsize, if they flip, they will not come upright again like a monohull.

Ways to Learn More

It takes skill to sail. You can learn the basics of getting a boat to sail in an afternoon, but to get mastery to navigate, sail quickly, and deal with some situations you can get into on the water like heavy marine traffic or bad weather, that takes time.

Learning what all the buoys mean should be done and familiarizing yourself with nautical flags is also smart.

There’s no substitute for time on the water for skill-building, but there are some ways to shorten the learning curve and help you make the most of your time on the water. 

Youtube is, actually, a repository of quite a few useful videos, like the one below.

When it comes time for you to think about buying your own boat, the more skill you have, the better decisions you’ll make.

Sailing Lessons

Every waterfront town with sailing has sailing lessons somewhere. Whether it’s a sailing school, a charter captain who will teach you for a few hours, or a community sailing center, there is always a way to get an instructor to give you the fundamentals, though it’s rarely free. 

Look for a school or center affiliated with a governing body like U.S. Sailing, Royal Yachting Association (RYA), or a training organization like the American Sailing Association (ASA), since those will have recognized standards and curricula.

Smiling, satisfied captain, bon voyage

Some sailing bodies and sail training organizations offer online training towards certifications. These can be solid tools to get you the theory you need, especially in the winter. But you will still need to get on the water to put it into practice. The ASA, U.S. Sailing, and the RYA offer courses which combine online training and on-the-water lessons.

Studying Up

Besides online coursework and surfing the web for videos and how-to articles, books and magazines can help you get more information and knowledge. Consider subscribing to some magazines well before you buy a boat; they’ll help you get an idea of the market for boats and gear and many practical tips.

Crewing for Others

Other people’s boats are great places to learn. Most club races have boats with spots for new sailors, and almost every sailor you meet is going to encourage you and want to help you learn. Even if you never want to race your own boat, a summer spent sailing in a low-key racing series at a club near you will do wonders for your sailing skills.

Facebook is actually a decent way of finding sailing clubs and networking with people who could use company for a day sailing. That’s free experience, potential friendships and a way out onto the water.

Facebook Sailing Groups

Wangling an invitation to spend a weekend with someone is a little trickier if you’re not already friends with a boat owner. But let people know your availability, since some skippers may want an extra pair of hands for their boat.

Getting on the Water Before You Buy

Turning an interest in sailing into a lifelong passion takes getting out on the water, something that isn’t so easy before you’re willing to commit to owning your own boat. But there are a few ways you can easily get some tiller time. They’re not free, but they are reasonable and free of the responsibilities of ownership.

Community Sailing Centers

All along the coast, you’ll find community sailing centers you can join. Their mission is to promote sailing and make sailing more available to everyone. Most offer lessons, and most have a fleet of small boats for member use once you’ve taken some lessons or passed a skills test. 

Typical costs may run around $200 per person, though family memberships are usually cheaper, and many offer youth sailing.

Boat share clubs

More expensive than a community sailing center, boat share clubs give you a broader range of larger and more complex boats than the dinghies and daysailers you’ll find in a community boating center. You pay annual or monthly fees, reserve boats, and can choose from a variety of sail and powerboats. 

Once part of the club, you’ll get access to the fleet of sailboats and motorboats too. That includes bowriders, pontoon boats, and even cabin cruisers. For fishing, some clubs also have the very cool jon boats too.

Bowrider Motorboat

So learning to sail through clubs also gives you access to try myriad other vessels. And since they want to protect the club fleet, most clubs offer training at a rebated membership price.

Check out some peer-to-peer boat sharing opportunities as well. Google “boat sharing near me” and you’ll find some results. Or look up: rentaboat.com, boatsetter.com, samboat.com to find some sharing chances.

Rentals

If you live near a boat rental concession, you always have a commitment-free way to get on the water. There won’t be any dues or membership, but you will pay hourly or for blocks of time as you use them.

Yacht Clubs

Join a yacht club without owning a yacht? It’s more common than you think, and many yacht clubs have cheaper “social” memberships for those who don’t own boats. What the club offers you is access to sailors and boat owners, social events, and maybe even sailing lessons or boats to use or rent. 

Small yacht sailing close to the shore

It’s a great way to meet people who want help in the weeknight races, or an extra set of hands to help handle the boat on a weekend away.

How About a Charter?

Chartering a boat is, hands-down, one of the best ways to learn if skippering a boat and cruising is for you. Even if you don’t have the skills to charter a boat yourself, chartering with a captain will still teach you loads and give you a good feel for life aboard. Many charter captains will teach you during your charter, and all captains will get you as involved with the sailing as you want to be.

Modern charter yacht moored to a pier in marina. Top down view of the wooden teak deck, mast and sails. Mediterranean sea. Private vessel for rent, cruise, recreation, leisure activity, sport, regatta

You can also check out different styles of boats to see which suits you better. A week on a monohull and a week on a catamaran will give you a very clear picture of the differences between them and why you may prefer one over the other. Most charters are late-model yachts in good condition, and very close to what you can buy on the new boat market.

Is it time to buy a boat?

When you have your own boat, you control your own destiny and can catch that feeling at any time. But are you ready to make the commitment? Boat ownership can be expensive and time-consuming, and buying the wrong type of boat for your skill level or buying a bad boat can spoil your love for what could be a lifetime passion.

Check your skills

The best way to get a good deal on a near-new boat is to find a skipper who bought a boat too big for his skill and is miserable because he can’t handle it without help or at all.

You do not want to be that skipper.

Cat and dog drift in a washtub 2

Before you take the plunge into a boat, you need to make sure you’re up for it. Take a realistic evaluation of your own skills, and consider that a small, simple boat may be a better place to start. 

Sure, that flashy fifty-footer at the show may tick all your boxes and set your heart aflutter, but it is much more powerful and mechanically complex than a thirty-five-footer. If things go badly, the forces are bigger. As are the repair bills.

While there is nothing limiting your boat choice but your bank balance, give some long thought to what you’re getting into. There is nothing wrong with a “starter boat” as your first boat, where the loads are small, the systems are simple, and you’re not committing as much money before you go all-in on your dream boat. A couple of seasons in a 30-40 footer and you’ll be ready to move up safely.

Look at your budget

Many boat services are charged by the foot, so the bigger boat you get, the bigger those expenses. And those aren’t related to the price or age of your boat – a twenty-five-year-old boat costs the same to keep in a slip or haul out as a brand new boat worth ten times as much.

Boats and yachts in port

Buying the boat is the first step. You’ll need to berth it for the summer, store it for the winter, maintain and clean it, insure it, deal with repairs, buy sails, get a tender if you cruise, and handle other unforeseen expenses. Most suggest blocking out at least 10% and up to 20% of the purchase price annually for expenses. Of course, that depends on the age and condition of your boat and how much you paid for it.

Before you look at boats in person, look into ownership costs in your area. Check out marinas and moorings to see what’s available year-round for the size and type of boat you’re considering. Look into all the costs, including hauling and dry storage.

Marina of Monte Carlo in Monaco

Money shouldn’t dissuade you from owning a boat, but it’s important to be realistic and be prepared. You don’t want to get in over your head without knowing you need to budget for more than the price of the boat.

Priorities

Boats are a time commitment. Not just for boat work or cleaning and maintenance. Every marina is full of boats that never seem to move. Their owners wanted a boat and thought it was a good idea, but the practical realities of their life meant that they didn’t get to use it as they dreamed.

Marina with a yacht storage rack

To get value out of your boat, you need to make time to use it. Boats are great for families, but kids with heavy summer schedules may end up keeping you home on weekends. Throughout the summer, you’ll find things to take you away from the water, and if you aren’t careful, the only time you’ll end up seeing your boat is to wash it in the slip.

If you can make sailing a priority for your recreational time, it will reward you richly.

FAQ – Frequently asked questions about Learning to Sail

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    Is it difficult to sail solo across the Atlantic?

    Depending on how well you know the vessel, usually a sailboat that’s more than 35 feet long, an experienced sailor can successfully sail alone across the Atlantic as long as they have planned appropriately.

    There are specific seasons for sailing either one way or another. Following the Gulf Stream from the Caribbean to Europe one way, or from the Canary Islands to North America the other way are usually done during a specific window of foreseeable winds.

  • image/svg+xmlimage/svg+xml
    Is it difficult to learn to sail?

    With the right approach to sailing–and respect for winds and waves–sailing is quite safe. But there are some hazards associated with a sailboat, as there are with motorboats.

    Read this introduction to sailing to figure out how you can learn to sail.

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