Your First Sailboat

Finally, after years of slow growth, the sport of sailing has the wind at its back. This resurgence is driven by cheaper boats that are easier to transport and navigate, the draw of doing something carbon-neutral and the thrill of wind-powered propulsion.


We’re not talking about starting your sailing adventure with a 55-foot ketch and a crew of seven, or becoming an America’s Cup racer where you hang over the side on a harness, traveling 34 miles an hour. The best starter sailboat requires a one-person crew with room for friends and family, with retractable tillers and centerboards to make them easily towed.

Most starter sailboats are affordable, particularly if you buy them used. 

Marinas and community schools offer “how to sail” courses that will teach rigging, sailing points (upwind, downwind, sidewind) and, most important, how to dock.


What’s the wind that’s pushing these trends? Boating in general and sailing in particular are getting a boost in a post-pandemic landscape. Working from home drives an urge to be outside in nature. Boating offers the joy of being out on the water, among fresh breezes. 

Sailing is a great family sport that teaches cooperation and leaves long-lasting family memories of being together on an adventure. 

Nothing is more thrilling than that feeling of being blown by the wind. Sailors enjoy the challenge of operating the boat and navigating different weather conditions. 

Sailing is a social sport. Sailors love to trade tips on sailing techniques, boat options and best places to sail. 

Another draw of sailing is its intellectual side. Sailors enjoy the challenge and complexity of reading the wind and responding with the optimal blend of a trimmed sail, the best course and the right amount of hull in the water. 

An Upscale Sport

Sailing draws an upscale crowd and is now the second most popular sport (to downhill skiing) among medium to higher income brackets. Among the affluent, sailing has become more popular than tennis, golf, canoeing and mountain biking. 

But access for beginners is quite reasonable. Small, used sailboats can be found for under $1,000, giving you an affordable entry point to get your sea legs and see if you like it. 

Sailing appeals to a range of personalities: adventurers, learners, outdoor enthusiasts, introverts and extroverts. It’s both a solo sport and a family sport, full of thrills, excitement and beauty. 

Grab a lanyard and give it a try! 

Popular First Sailboats


New: $3,500 | Used: $200-$300

Single mainsail craft that can be transported on top of a car and assembled in minutes.


New: $5,000 | Used: $1,000

A large sail and shallow draft make this 13-foot sailboat fast, with great rigging for learning and racing. Beware: easy to tip.

Gaff-Rigged Catboat

New: $20,000- $50,000*| Kit: $3,000

From 15 to 19 feet, with either an open design or cabin. At home on a lake or the ocean, with room for family and friends.
*without cabin or with cabin, galley and head

West Wight Potter 19

New: $25,000 | Used: $5,000

Fiberglass and literally unsinkable. Easy to rig and handle. Capable of navigating a lake or sailing from California to Hawaii. Stable. One person can set up and sail it, but room for lots of shipmates.

Your Timbers: Shivered 



In the early days of boating, sailors began
calling the right side the steering side, which soon became "starboard" by combining two Old English words: stéor or
(meaning "steer") and bord (meaning "the side of a boat").


The first control device that the jib (sail) sheet passes through on its way back to the cockpit.


A tiller or till is the lever used to steer the sailboat. A tiller is attached to an outboard motor, rudder post or stock.


The keel is a flat blade sticking down into the water from the bottom of the sailboat. The keel was made to prevent the boat from being blown sideways by strong winds.


Shrouds are symmetrical pieces of standing rigging that hold the mast up.


The boom is the pole that extends from the bottom of the mast. Adjusting the boom towards the direction of the wind is how a sailboat is able to gain wind power in order to move.

5 Stunning Places to Set Sail

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