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I’m standing at the helm of a 51-foot sailboat in the Caribbean Sea, approaching the island of St. Lucia, where my companions and I will anchor for the evening. As I spin the wheel slightly, the sails flutter and snap to attention. With the water beneath my feet and the wind at my back, I’ve never felt such an intoxicating blend of power, possibility and relaxation.

I also feel extraordinarily lucky to have been invited on this monthlong sailing trip, an experience that’s becoming more popular — and affordable — than you might think.

Community boating centers and inexpensive sailing opportunities abound. Deckhands of every age are learning the ropes (known on a boat as lines or sheets). And according to The Sailing Company, in Middletown, R.I., 1.6 million sailboats were used in 2006, many of them filled with first-timers on brand-new adventures.

“The reasons for sailing are as varied as the individuals and boats out there,” says Susan Peterson Gateley, who teaches sailing on Lake Ontario. “One big draw is the sense of freedom.”

And once you’re hooked, it can become a lifelong passion. “Sailing is something that gets in your blood,” says Dave McGinnis, manager and senior captain of Michigan’s Traverse Tall Ship Company. “Flying along with everything set in a perfect breeze, when the vessel comes alive in a balance of power and grace — it touches something deep in the core of your being.”

Sure, sailing takes skill, quick thinking and physical prowess. But thanks to hundreds of sailing schools and outfitters around the country, just about anyone can set sail, whether it’s for a three-hour tour — or a three-week voyage.

No Experience Necessary

Though you don’t need lessons to participate in many sailing adventures, learning to sail can be one of the most rewarding ways to get on the water. The American Sailing Association certifies more than 270 facilities around the world to teach sailing basics. Classes range from two-hour primers to longer courses in racing, cruising, navigation, and more. (Some experienced sailors enroll in refresher classes so they can “bareboat,” or charter a vessel without a crew or provisions.)

“You can learn the basics in a couple of hours,” says Steve Mink, co-owner of the Liberty Sailing School of Philadelphia and a U.S. Coast Guard–licensed captain. “And then spend the rest of your life developing those skills.”

In Liberty’s two-day “Basic Keelboat” class, students split their time between the classroom and the water. They learn key sailing knots, names of boat parts (including tiller, boom and mast), how to rig and hoist sails, terms such as “beam reach” and “close hauled,” how to turn the boat by tacking or jibing, and much more.

When Laurie Davis of Indianapolis signed up for a sailing class in Florida last June, she had no experience on a boat. All the new terminology was confusing at first, says the 60-year-old retiree, but she soon gained the confidence to steer the 26-foot sailboat on her own. “It was so exciting to take the tiller and try to find that perfect point on a beam reach where you’re just hanging over the water and going so fast.”

Typically, the only gear you need to bring to class is weather-appropriate clothing, boat shoes and personal refreshments. Handling the sheets and pushing the tiller take minimal strength, and unlike many sports, sailing has virtually no restrictions on gender, age or abilities. Most marinas, including the Geneva Lake Sailing School in Fontana, Wis., even have special programs for kids. Rhode Island’s nonprofit Shake-A-Leg organization promotes its Adaptive Sailing Program with specialized boats.

Many community boating centers — on ocean bays, lakes and rivers — offer deeply discounted programs. In Boston, for example, children pay $1 for membership in ˙ the Junior Program at Community Boating, Inc., while the adult 30-day intro to sailing and kayaking is just $90. Many instructors are thrilled to donate extra hours to teaching. “When I see people enjoying that experience for the first time, it charges my batteries,” says Mink.

Life at Sea

Don’t want to hit the classroom before hitting the water? No problem. There are plenty of other sailors who are happy to steer while you sit back, relax and enjoy the ride.

Sailing adventures offer a wide range of activities: from short, relaxing cruises on a river to multiday excursions on the high seas. While the crew sails the boat, you can learn to paint, watch for whales, fish, cook, study a new language or simply kick back. Or, if you want to feel like part of the crew, they’ll let you help hoist the anchor, trim the sails and even steer.

Most companies also allow on-shore time. Maine Adventure Sails, based in Rockland, Maine, offers three- to six-day trips on its schooners Timberwind and J. & E. Riggin that include beach lobster bakes and island hiking (the eco-friendly sailors even pick up litter along the trail).

“I love feeling the wind in my face, the fog — out of which appear islands, birds and seals — the stars at night, and hearing the crew sing,” says Louisa Enright of Camden, Maine, a regular passenger on the J. & E. Riggin.

Maureen Riley has also sailed on the J. & E. Riggin — 34 times. Onboard, the 54-year-old nurse anesthetist from Royal Oak, Mich., has taken a photography seminar, seen the Northern Lights, raised the anchor, heard steel-drum bands and met friends for life, all while blissfully cut off from cell-phone calls, television and radios.

“Most weeks,” she says, “you just forget that the world is out there.”

Sailing Dos & Don’ts

  • Do wear sunscreen, since rays reflected off the water can increase the risk of sunburn and sun damage.
  • Don’t risk dehydration. There may be “water, water everywhere,” but it’s best to bring your own potable liquid in a reusable, unbreakable bottle.
  • Do leave the flip-flops at home. Many sailing schools recommend nonskid boat shoes and frown upon black soles, which leave marks on the sailboat decks.
  • Don’t ignore the captain or instructor. “You can capsize and drown even on a tiny lake,” says Susan Peterson Gateley, who teaches sailing on Lake Ontario. Tuning in will help prevent you from getting tossed out.
  • Do avoid seasickness by trying ginger, Sea-Bands and MotionEaze, alternative remedies suggested by Sailing magazine. Or, ask your doctor about prescription treatments.
  • Do know where life jackets are stowed in case of rough waters or an emergency. Nonswimmers and children under 12 should always wear a life jacket (check your local boating regulations for requirements).

Sailing Terminology

  • Bow: The front of the vessel
  • Stern: The rear of the vessel
  • Port: The left side of the vessel (when you’re standing at the stern, looking at the bow)
  • Starboard: The right side of the vessel (when you’re standing at the stern, looking at the bow)
  • Sloop: A vessel with a mast and two sails; the most common type of sailboat
  • Jib: The front sail or headsail
  • Mainsail: The aft sail in a sloop rig (at or near the stern)
  • Halyard: The rope or line that hoists up the sails
  • Sheets: Ropes or lines that hold the sails in position
  • Trim: To adjust the sails
  • Tacking: Changing course or direction by steering a vessel into the wind
  • Come About: Turning the vessel’s bow through the wind
  • Jibing: Turning the vessel’s stern through the wind
  • Bowline: A temporary, nonslipping loop in a line
  • Cleat: A fitting to which lines on a vessel are secured
  • Tiller: A lever attached to the rudder for steering the vessel
  • Downwind: With the direction of the wind
  • Upwind: Opposite the direction of the wind
  • Spinnaker: A light, kite-like sail used when sailing downwind


Sailing Schools

Explore these sailing resources for classes and getaways that suit your schedule and budget. Most sailing lessons cost from $100 for a two-hour class to more than $4,000 for a weeklong class; trips can range anywhere from $50 for a one-hour cruise to thousands of dollars for a multiday adventure.

U.S. Sailing: The national governing body for the sport maintains an online database of nationwide sailing schools and community sailing programs. 800-877-2451;

American Sailing Association: This association has accredited more than 270 sailing schools around the world. 310-822-7171;

Offshore Sailing School: More than 100,000 sailors have graduated since 1964; choose from 10 locations and more than a dozen different courses for all sailing levels. 800-221-4326;

OCSC Sailing: With a fleet of more than 50 boats on San Francisco Bay, this school arranges lessons and trips around the world. 800-223-2984;

Sailing Adventure Outfitters

Maine Adventure Sails: Full crews steer up to 24 passengers on three- to six-day trips on the schooners Timberwind and J. & E. Riggin; call for current rates and packages. 877-300-3377.

Lakeshore Sail Charters: Board a 36-foot sloop or a 77-foot schooner to see Chicago from Lake Michigan during happy hour; night or day sails. 708-769-4220;

Monterey Bay Sailing: Choose from nature excursions, corporate team-building yacht races and three-day cruises on the bio-diverse Monterey Bay. 831-372-7245;

Sailing Ship Adventures: Book a trip to Denmark, Italy or beyond; this company works with a fleet of more than 100 tall ships, some longer than 400 feet, that can accommodate as many as 225 passengers. 877-882-4395;

Traverse Tall Ship Company: Chill on the 114-foot-long Manitou, a “floating bed & breakfast” that accommodates up to 24 guests in 12 private cabins; two-hour to four-day sails on Lake Michigan and its bays.  800-678-0383;

The Moorings: This yacht charter company allows you to sail a boat yourself or hire a captain, crew and cook; destinations range from the islands of the Caribbean to the Mediterranean to the Kingdom of Tonga. 888-952-8420;

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