How to Learn to Sail

Boat projects abound. Still, it's fun to reflect on how I got to this point. A few people have asked me for advice on learning to sail, since that's probably a pretty important part of this sailing life. Right?

I learned to sail on a glacier lake in the Northeast Kingdom of Vermont, where the boats we have are old and water-logged and sluggish in the best of winds. My version of sailing, shared by others who also had no real clue about the sport, was one of flogging sails and a whole lot of paddling, spiced by a too-short tiller extension and a centerboard that slipped out if we heeled too far. I learned that sailing was a sport of independence, of frequent mishaps, and maybe, if you were lucky, some moments of sheer bliss. There was also a lot of paddling and swimming.

This is not the ideal way to learn to sail.

My best friend in high school went on to represent the United States on the sailing team in 2 separate Olympic games. From her, I learned the importance of the proper terminology for all parts of the boat, as well as the joys of actually sailing a boat that moved with the power of the wind. When I had the chance to sail with her, on her family’s boat on Lake Ontario, I was treated to a world where the wind was your partner, not something you fought against every second of the time. I learned that sailboats are gorgeous, you can’t tell how much closer you are to the finish line than the other guy until you’re pretty close to it, and big boats shouldn’t involve swimming as a way to get back to shore.

This was a better way to learn to sail.

When I got to college, I decided I’d further my sailing education and joined the sailing club. I went to the University of Virginia, which is situated in land-locked Charlottesville, and we practiced on a man-made lake 30 minutes away from the school. My skipper took pity on me and taught me about hiking out to keep the boat flat, the joys of a well-executed roll tack, and how to rig a 420 while trying to keep your fingers warm. We did, often, sail in cold weather. These college sailing days were filled with laughter and work, endless road trips and late nights of car rides and conversations. Friends introduced me to teaching at Sail Caribbean, a teen sailing camp in the Caribbean where I spent my days teaching teenagers on 50’ sailboats the joys of all aspects of life aboard. Sailing is friendship, cooperation, muscle memory, and travel – and maybe, if you’re lucky, a little money-making on the side.

This was, so far, the best way to learn to sail.

After college graduation, my husband and I bought our own 28’ boat and took off, spending 3 years wandering the Bahamas and the Eastern Caribbean before heading up the East Coast and settling down in Charlottesville. We had to be self-sufficient in ways no 20-year-old thinks about, and every 20 year old ought to experience. From learning the hard way that you better fill your water tanks to the brim before you shove off the docks the first time, to anchoring 5 times for 4 named storms our first year out, to blissful days tacking in and out of anchorages along Venezuela’s bay-studded coast – life was full of adventures both amazing and terrifying.

*Then, when you get older, you can teach your parents.*

If I had to choose it all over again, I’d pick the last one as my favorite way to learn this sailing thing.

Maybe. Maybe not.

Thing is, all of these had one thing in common. Whether good or bad, all of these involved actually getting on a boat and shoving off from land. I learned something from every single encounter I had with a hull that had a mast stuck in it; actually, I still do. The best way to learn to sail is to get out there and sail, no matter how you get a chance to do it.

If you’ve got access to a cold lake and a heavy old boat, go for it. If you can learn from someone who’s the best of the best, go for it. If you pick up a book, or watch YouTube videos, and then get on a boat and try and try and try again – that’s a perfect way to learn to sail. If you have the opportunity to sail on a large boat in the sun-filled Virgin Islands, or somewhere in the tropics, I can promise you you will learn something.

But what if you’re older, not starting out as a kid or in high school or in college. What then? Is it too late?

There’s a favorite saying that the best time to plant a tree is 20 years ago. The next best time is now. Same holds true with sailing. You might have more patience now, more ability to be deliberate. You might listen better, or research more, or have the funds to pay a decent instructor. Don’t let age deter you from trying something new!

If you’re a parent, lamenting the fact that you are just learning and you want your kid to learn earlier in life than you did, get out on the water. Sure, let them join a junior program or do a sailing-focused camp or send them off to Sail Caribbean or another of the sailing schools designed for teens around the world. Just get them on the water, messing about in boats. Go with them, learn together, and play.

The best way to learn to sail? That’s the way you do it. Stop researching, grab your PFD*, and get out on the water. I bet you won’t regret it.

See you out there.

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