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One of the world’s oldest sports is more approachable than you might think.
Caleb Paine, 2016 Olympic Sailing Medalist
Mar 30, 2021
I grew up in San Diego, and I feel about sailing the way surfers talk about surfing. “Just out there with the waves, man . . .” I actually live on a boat. Sailing is especially exciting for first-timers. One of the coolest things is sailing upwind, even just around the bay. You’re going to feel the wind on your face, you’re going to hear the sail. A big boat comes by, and there’s a wake. You hear the waves splashing and feel the boat heel to one side. All of a sudden a couple dolphins pop out of the water. And all this stuff is sensory information that helps you determine what to do. The sound of the sail tells you if it’s luffing, if it’s not trimmed properly. The way the water moves foretells a coming shift of the wind. That’s what’s special about sailing: The connection you make with nature is a consequence of your making the boat move. Sometimes, when you’ve got everything perfect, it goes quiet, and all you can hear is the hull going through the water and the breeze pushing past you. It’s primal. Spiritual, even. Just out there with the waves, man.Find a Place To LearnBetween the American Sailing Association and U.S. Sailing, the two main certifying bodies, there are a few hundred sailing schools around the country—even in unexpected places like Oklahoma and Arizona. Beginner’s courses often last two days, so you can find weekend packages. Expect to pay about $500 per person. At higher levels U.S. Sailing emphasizes racing and the ASA pleasure boating, but introductory classes are more or less the same.Understand What’s HappeningSailing is rich with jargon, tradition, and lore. You’ll better absorb the complexities if you know the basics ahead of time.
How wind moves a boat: A sail full of wind forms an airfoil and propels the boat with lift, the way a plane’s wing does (except across water, rather than into the air). The work of sailing is to position, or trim, the sails to maximize lift in the direction you want to go.Once you’ve raised the sails using the lines—never say “ropes”—called halyards (A), they’re trimmed using the sheets (D), which pivot the boom (E) between the port and starboard—that is, left and right—sides of the boat. On a two-sail boat like this one (called a sloop), the emphasis is on the mainsail (B), the sail nearer the stern (H), which is the rearmost or aft part of the boat. The smaller jib (C), nearer the bow (F), at the fore, also pivots—but as a new sailor you’ll be focused on the mainsail.The basic idea: You use the tiller (G) to move the rudder (I) and angle the boat so that it is perpendicular to the wind. Use the sheets to angle the mainsail so it fills with wind. In the bowing airfoil shape, air moving over the longer, curved side moves faster than air flowing by the other side, generating lift."Tying Off" a "Line"At some point you’ll be asked to secure a line to a cleat. Here’s how, using a simple knot called a cleat hitch.
Starting with the horn farthest from the load, wrap the line around both horns. (Only once—more increases the odds of jamming.)Make at least two figure-eight turns around the cleat.Secure the free end of the line by tucking it under the last turn.Get EquippedAny skipper taking you out for a lesson will have safety equipment and navigation hardware. Your main job is to dress for the occasion. So: Picture a sailor in your mind—then don’t dress like that. You don’t need a cable-knit sweater and pipe. Check the forecast and wear the layers you’d wear on land—plus make sure to have these four things.
Force 12 PFG Shoes
Two requirements for deck shoes: They must be grippy and non-marking. With a Vibram Wavegrip sole, the Columbia Men’s Force 12 PFGs meet both and offer a third advantage: They look great.
Polarized Rectangular Sunglasses
Costa Del Mar
Polarized sunglasses cut glare so you can see how the water is moving, helping you read the wind. Costa’s optics are second to none. We recommend its Slack Tide shades with mirror lenses, which increase contrast between subtle changes in water conditions.
Atlas 300 Rubber Gloves
Expensive sailing gloves can push $50. Showa Atlas 300 heavy-duty gloves are around $25...for a 12-pack. They work just as well, and if you want your fingertips exposed (to improve dexterity), you won’t feel bad taking a scissor to ’em.
The Ship's Log
The logbook is where you keep track of the classes you’ve completed and the hours you spend on the water. If you ever want to charter a boat or become an instructor, it’s a handy way to demonstrate experience. And even if you don’t, keeping a tangible record of accomplishments is an underrated pleasure.
HP Fjord Jacket
A layer that can stand up to wind is non-negotiable. Helly Hansen’s HP Fjord is an excellent barrier to both wind and water, and there’s just enough heft to it to offer a little warmth, too.
Should You Buy a Boat?Actually, yes. If you’ve caught the bug, a good entry point to boat ownership is a Sunfish, a 14-foot dinghy with a single sail. New, a Sunfish can be had for about $4,500, but they’ve been around since the early 1950s—with several hundred thousand in existence, there’s at least a couple out there in decent shape at a much lower price.
If you’re feeling more enterprising and can find a copy of the 1950 classic Popular Mechanics: 23 Boats You Can Build, the Su-Lu plywood dinghy offers a decent approximation of a Sunfish.FAQ for the First-Time SailorWhat if there’s a gust of wind? Will the boat capsize?When there’s a big gust, you simply turn into the wind, which stops the boat. And luckily, the heavy ballast below a keelboat’s hull makes them pretty hard to capsize. So while a strong gust may cause the boat to heel, or lean, you’ll be fine.Will I get seasick?You might—though while learning, you’ll be close to shore, and being able to see land generally helps. If you’re about to vomit, for the benefit of all involved, head to the leeward side of the boat.If I fall overboard, can the boat make it back to me in time to save me?Make it known that you’ve hit the water and someone will toss you a flotation device (if you aren’t already wearing one). Then, it’s going to briefly look like the boat is sailing away. Don’t freak out. It just takes time to turn a sailboat around.How hard is it to work the sails?Wind-filled sails can take serious strength to manage, but tools like pulleys and winches give sailors a mechanical advantage. As a casual pursuit, anyone can sail. (Racing is another matter.)
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