How To Get Started With Sailing


Last Updated by

Daniel Wade

February 19, 2020


Have you ever looked at a sailing regatta from the shore and wished you could get onto one of those boats? The yachts look picturesque, glamorous, unreachable. You briefly entertain the idea of being at the helm of one of those boats but close out your daydream with a sigh; it seems like you’d need a million bucks and just the right outfit to talk (and buy) your way into a yacht club.

But here’s the best-kept secret about sailing: you don’t actually need deep pockets to get started. There are a thousand and one ways to learn how sail on a budget, because the majority of sailors are on a budget. It doesn’t cost a million bucks—all it takes is a little research, some time, and a lot of persistence!

To get started with sailing, you’ll probably either take a sailing course, get invited onto a boat, or a rent a boat. Most sailors learned through some combination of the three. And while most have strong opinions about sailing, they all agree that there is no one “right” way to learn.

Here's a peek into how three sailors got started on their journey:

Table of contents for this article

An East Coast Sailing Journey

Vinay, a 35-year-old engineer, had been wanting to learn how to sail ever since he moved to Boston from Kansas. The Boston area has an abundance of sailing opportunities on the Charles River, the bay, and the ocean. During spring, summer, and fall, the waterways are filled with sailboats of all shapes and sizes. The river is a collage of boats crisscrossing and heeling at different angles and speeds. Dozens of two-person FJ race boats with colorful sails used by college sailing teams look like a swarm of butterflies as they swoop around from one racing buoy to the next. A scattering of four-person keelboats with beat-up sails mill tightly near the esplanade, bounded by an invisible fence defined by the boating club they belong to. The gaff-rigged Lynx Catboats from the MIT boathouse lumber along, dragged by the weight of too many people on board. Their turning radius is as tight as a bus and they technically seat 8 people. Apparently, the unofficial record is 20 undergraduates.

A year after he moved, Vinay met a sailor named Liza at a party. She was a member of Community Boating, a nonprofit whose motto is “Sailing for All” that makes learning how to sail easy and accessible to locals. Liza was skippering a keelboat the next day and had an open spot for crew. Vinay joined her group, and the four sailors split the $89 boat rental fee for the 19-foot boat.

“It took a lot of control to stop myself from blurting out the lyrics to ‘I’m on a Boat’ by The Lonely Island—I was so stoked to be sailing! I signed up for a sailing class that day,” he said.

Vinay learned the basics of sailing by taking courses at Community Boating and renting their boats that summer. There, his social network expanded, and he started meeting more sailors. He was having fun with Community Boating, but being a competitive guy and an engineer, he was drawn to racing. When he learned about the dinghy racing program at the Boston Sailing Center, he signed up for their crew list and was soon learning to rig and maneuver different boats. He loved the challenge of getting the boat to go as fast as possible by trimming the sails, hunting for the best lane on the race course, and tacking and jibing strategically.

“I learned so much more through dinghy sailing than I did on the big keelboats. With a dinghy, you feel every movement of the boat and the wind—you actually feel the physics. Even today when I’m racing big keelboats, I always choose crew who learned on a dinghy,” Vinay said.

After three race seasons—including a season of “frostbite racing” on J-24s every Saturday during the freezing Boston winters—Vinay became curious about bigger boats and started networking his way to crewing for captains of larger race boats. At the same time, he wanted to learn to skipper bigger boats as well, so he began taking American Sailing Association (ASA) courses at the Boston Sailing Center. Ten years later, he’s still happy sailing other people’s boats—as a guest, crew member, or skipper.

“You learn so much when you sail on different boats and I don’t want to deal with maintenance! My advice to anyone who wants to sail is to just do it—go out there and find a sailing club and figure out their system. Loads of places have boats you can use—you just have to look for them,” he said.

A Midwest, Middle Eastern, and European Sailing Journey

Meanwhile, Kylie, a 42-year-old teacher, learned to sail in sprints separated by long pauses. She grew up in Michigan, where her family rented the same one-room cottage near a small lake each summer. Her mother loved learning how to sail on the ocean when they lived in San Diego when Kylie was a toddler; she was determined that her 12-year-old daughter have a chance to learn. When she saw a Sunfish dinghy for sale for $100, she snapped it up and brought it to the cottage.

“We had no idea how to rig this thing, but the Sunfish is a simple boat so we kind of just figured it out. I’m sure we didn’t get everything right,” Kylie laughed.

Kylie's mom taught her the basics. This is the steering thingamajig. You can't sail straight into the wind—that’s called the “no-go zone." Watch the boom so you don’t get hit in the head. Kylie shoved off from the beach, pushed the centerboard down, and it was love at first gust.

“You’ve got to understand that this was a tiny lake. It had never seen a sailboat. There were a few canoes and rowboats that people would take to get to the other side of the lake, which was probably 500 feet away. But sailing was totally different! I’d go back and forth, and back and forth—if there was a good wind, I’d have to tack or jibe about every two to three minutes because there was just this tiny radius in the center of this lake that was deep enough for a two-foot centerboard. People thought I was crazy. It was a blast,” she said.

When she went to college in Connecticut, she jumped at the chance to learn how to sail “for real” through the sailing program at school. It was also a small lake, but at least 20 times bigger than the one she had learned on, and here they could teach her how to rig the boat properly. The 14-foot dinghies were perfect for learning, and for the first time she found out that everything on a boat had a name. And even on a small boat there were a lot of things with names!

“I’m terrible at remembering names and new words. I’m not great at the theory either—I barely passed the written portion of the college’s certification test for the dinghies. I just feel my way through the wind and the boat—I’m more of an intuitive sailor than a technical one,” she said.

After college, Kylie lived in places where there wasn’t much sailing and she didn’t make an effort to find opportunities to sail. Until one day, when she found herself living and working in Dubai.

“Sailing was my sanity there. It’s not a place with a lot of access to nature, so when I found out there was a sailing club that had its own boats I could rent, I was determined to join. The waiting list was long, and I tried to ingratiate myself by being useful at the club. I’d volunteer on the race committee boat, help the instructors put stuff away, and all that jazz. It was one of those places where you had to get three members to sign your application to join the club. I was a little shy about asking people for a favor. My friends found out I was too shy to ask, and they teased me so severely (and still do, 10 years later!) that the next day I marched into the club and asked three strangers to sign my form. And they did! That was the first of many life lessons I’d get from sailing!”

Kylie started sailing 14-foot Lasers and J22’s out of the club, sometimes solo and sometimes with friends. One day she and her friend Silvia took out a new boat—the Laser Vago—which has a trapeze that allows a sailor to counter the weight of the wind on the sail.

“The Vago was probably my most fun day sailing ever. We had a good strong breeze, and Silvia and I just had this perfect chemistry — it was like a ballet. I was out on the trapeze, and every second we needed to slightly adjust the tension on the trapeze, the trim of the sail, or the angle of the boat. I controlled the weight, and she controlled the sail and the angle, so if one person moved, the other one was affected. And, of course, the wind was constantly shifting. But somehow, we were totally in sync. Until we weren’t and we capsized! Normally on a dinghy it’s really easy to get back upright, but for some reason this one was really hard. Neither of us weighs that much, so righting the boat took effort. One of the yachts from the club cruised by asking if we needed help. It was full of guys, and there was no way Silvia and I were going to admit we couldn’t do this on our own! We regretted it briefly thirty minutes later when we were still turtled. But we righted the boat in the end and had a good laugh and a cool beer after we sailed back to the club.”

Kylie got more into sailing over time and decided to get certified so she could charter a cruising yacht someday. Over two years, she took two week-long courses accredited by the Royal Yachting Association in Croatia and kept sailing through the Dubai Offshore Sailing Club. After she left Dubai, she never let a sailing hiatus last that long again.

“There’s just something special about being out there. I like to say that troubles can’t follow you onto the water—whatever is happening in your life on land, it doesn’t make it out onto the boat. It stays ashore and your mind clears.”

And what about learning on dinghies versus big boats?

“I love sailing on both, but they are different. For me, big boats are fun because it’s a social thing and few vacations compete with chartering a cruising yacht in some gorgeous warm place. But you lose some of the feel of what’s going on with the wind on a big boat—I love the intensely physical nature of dinghy sailing. If you’ve had a good day out there, hiking out on a Laser, your abs should be seriously sore. I love that feeling!”

A West Coast Sailing Journey

Moving on to California, Bob, a 55-year-old software sales guy, first found himself on a sailboat when he was ten and his brother Jim was twelve.

“Somehow we’d scraped together enough savings and coins to rent this 12-foot dinghy on Pinecrest Lake. We didn’t tell anyone—least of all our parents—what we were up to. This was the seventies, so there wasn’t any of that liability nonsense you have going on today.”

The brothers figured out the boat well enough to potter around the lake for an hour or two. Their parents eventually figured out it was their kids out there on the boat, and they seemed to be doing just fine.

“It was so much fun! That day stuck in my memory enough to drive me to find sailing classes nearby a few years later. But that was a waste of time. I didn’t learn anything there,” he said.

Fast forward fifteen years. One day, Bob found himself on a 14-foot Hobie Cat with his friend Cliff in the ocean near San Diego.

“That boat was the bomb! Soon as I got on, I wanted one.”

Soon after, Bob was at a party in San Francisco. He told Jose, a guy he met there, that he was looking to buy a Hobie Cat. Serendipity swooped in. It just so happened that Jose had a Hobie 16 for sale.

“Cool. How much?” Bob asked.

“I’ve listed it for $1400, but it’s really only worth $700,” Kevin replied.

A handshake and a few beers later, Bob had himself a boat. He had no idea how to sail it.

A week later, he called his friend Andre, the one who is always up for an adventure, and asked if he wanted to go sailing with him. Andre showed up with a cooler and two 6-packs, ready for a good time. Aware that his sailing skills were a little rusty, Bob had chosen a place to put in where there wasn’t much traffic or wind. Richardson Bay is a calm, shallow bay tucked into a northwestern corner of the San Francisco Bay. Their destination was Chevys, where the laughter and margaritas were plentiful. Between Richardson Marina, where they set the Hobie 16 afloat, and Chevys, there happens to be a 1200-foot-long bridge supporting a major thoroughfare. The Hobie 16 needed to sail under the bridge to get to the destination.

At nearly 27 feet, the Hobie 16’s mast is impressive. It takes a strong sailor to bring that mast up and down, but Bob and Andre had no trouble rigging the boat and bringing her into the water. They got the sails up, and the light breeze made for a perfect sail. Bob and Andre were thrilled, enjoying their beers and their new hobby until Andre looked ahead and said, “Bob, I don’t think we’re gonna make it!”

“Not gonna make what?”

“We’re not gonna clear the bridge!” Andre yelled a second before the mast hit the bridge. Luckily the breeze was light, and they hadn’t been going too fast, so no one was hurt. But they were certainly in a pickle! The wind was pinning them against the bridge, and the top of the mast poked above the guardrail. Cars began to slow down as drivers rubbernecked to check out the bizarre pole and sail emerging from the guardrail.

As the two scratched their heads to figure out what to do, traffic was building up on the bridge. Eventually they heard a voice call down from the top of the bridge. “You two alright down there?” It was a highway patrolman. Andre looked at the policeman, opened up the cooler of beer and counted out loud: “One, two, three, four, five, six, seven, eight—Yeah thanks, we’re good for at least another hour!”

Bob and Andre found a solution. First, they dropped the sails, which decreased the pressure of the mast on the bridge. Next, they lowered the 26-foot mast, resting it lengthwise across the 16-foot boat. Now they could paddle the boat away from the bridge.

So, did they turn around and go back to the Marina?

“Heck no! We still had to pay homage to Chevys. We’d brought the boat all the way out there so we could rock up to the bar in a boat. No way we were turning around!” Bob said.

After his maiden journey on the Hobie 16, Bob began to take the boat to a slightly more challenging place each time. When he mastered Richardson Bay, he moved on to Redwood Shores, where there was a little more wind. Once he felt comfortable there, he moved to Lake Elizabeth. After a few months he took the boat to Redwood Creek, where he’d launch and tootle around in a mile-long creek that ended in the San Francisco Bay. Eventually he made it out to the bay.

“After that, I was off to the races. The San Francisco Bay is one of the hardest sailing environments there is, so once I felt good there, I knew I could go anywhere.”

The next season, Bob began taking his Hobie 16 to Santa Cruz, where there is an active Hobie racing and ocean sailing community. He’d usually sail once a week, getting to know the other sailors and learning how to land the boat in the surf. He’d had the Hobie for 25 years before he started to get tempted by bigger boats. He took a few American Sailing Association courses, building up to the ASA 114 Cruising Catamaran Certification, and chartered his first 45-foot Bali 4.5 Catamaran out of the Sea of Cortez in La Paz.

“It’s the same and totally different! The sailing is easy—there are a lot more ropes and such than the Hobie 16 but it’s the same kind of thing. I’m totally comfortable with that. The stuff I need to learn now is all the boat systems and navigation and such. Now I want to buy a broken diesel engine and fix it, so I know everything about marine diesel engines.”

Your Sailing Journey

So how do you actually get started sailing?

First, find a way to get on a boat! Tell everyone you know that you want to learn how to sail, search for local sailing communities, and if there aren’t any communities nearby, consider planning your next vacation around sailing. Look for dinghy or small boat sailing classes either through the ASA, the Royal Yachting Association, or perhaps through a sports-oriented resort that has a few sailboats. Protip: If you’re scheduling a vacation around dinghy sailing, do it someplace warm! Not having to contend with wetsuits or feeling cold makes a big difference when you’re learning. Make it a priority, and you’ll find yourself on a boat soon enough.

Second, meet other sailors. The more your social network includes other sailors, the more opportunities will come your way. It’s easy if there are sailing communities nearby that has classes, boats you can rent, and other sailors to meet. Most sailing communities are far more down-to-earth than the Ralph Lauren advertisements would make you think. If there aren’t any communities close to home, start using holidays and weekend getaways to get sailing.

Third, figure out your long-term strategy for sailing regularly. If there’s a community with boats you can borrow or rent, that’s a great way to get to know lots of different boats.  If that’s not an option, consider buying a dinghy. Check out Craigslist for Lasers and Sunfish. Even if you’re looking to race or charter big boats, starting on a small boat for a season or two will make you a better sailor. If you’re into racing, find ways to crew. Tell everyone you know that this is your passion, and the word will get out.

One thing is clear from Vinay's, Kylie's, and Bob’s stories: learning to sail is incremental. It doesn’t really matter where or how you start—chances are you’ll try a few different types of boats and like some more than others. Eventually you'll find your groove and before you know it, you’ll be reminiscing about those first sailing experiences with a big smile.

How To Get Started With Sailing

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