Best 5 Sailing Adventures

Of all the ways we’ve harnessed elemental forces to carry us from place to place, sailing is most exhilarating … and serendipitous. Aboard a tall-masted relic of the Age of Sail, a racing yacht, or a pleasure boat, you can let go of the need for an itinerary. Embrace the all-hands-on-deck camaraderie, or be as idle as you’d like. A sailboat can be your floating hammock, your refuge, your passage to uncharted waters within.

America’s Cup Charters

The sleek yacht heels over, shifting your equilibrium; the flapping of sails tickles your ears. You might reach 10 knots (about 11.5 mph) on a cruise aboard Intrepid, American Eagle, Weatherly, or Nefertiti, and it’ll feel like flying. As America’s Cup winners or contenders during the ’60s and ’70s, these sailboats were born to race. And they still do: The whole fleet will compete when Newport hosts America’s largest-ever gathering of historic 12-meter yachts July 8–13. Newport, RI. 401-849-5868; americascupcharters.com

Maine Windjammer Association

In all the world, there is no collection of boats quite like this: Four are National Historic Landmarks; the newest windjammer—Heritage—was hand-built by its long-married captains in 1983. And while accommodations are varying degrees of rustic, your sail on Penobscot Bay will be softened by the sounds of guitar strumming, the mystic glow of moonrise, and the promise of unlimited lobster. From a three-day jaunt to a 10-day voyage, the experience will make real-world reentry bitter-sweet. Rockland and Camden, ME. 800-807-9463; sailmainecoast.com

Moment Sailing Adventures

Entrepreneur and lifelong sailor Chris Bartick invested 10 months of loving labor getting the Moment, a classic Stevens 47, shipshape—and the result can be your special vessel for a proposal, “weddingmoon,” or just a few hours of gliding on southwesterly breezes in sheltered Provincetown Harbor. Captain, chef, and ordained minister Craig Hawley takes the helm for most charters and will cater to your whims, whether you want to moor and swim or lounge and savor lobster guacamole. Up to six people can enjoy a two-, four-, or six-hour cruise; one or two couples can book a 48-hour jaunt that includes time ashore in Wellfleet and Plymouth before they’re rocked to sleep in their private staterooms. Provincetown, MA. 347-857-7245; momentsailing.com

Mystic Whaler Cruises

In their playful banter, their devotion to preserving nautical traditions, and their obvious care for the 83-foot Mystic Whaler and its guests, husband-and-wife captains John Eginton and Pat Beck set the tone for every sailing. And no boat in the region undertakes a more diverse lineup for all tastes and budgets: A luncheon, sunset, lobster dinner, or Sunday brunch cruise is an easy way to get out on the water, while two-to-five-night themed trips with enticing ports of call like Block Island and Jamestown and bright, comfortable cabin accommodations make a sailcation attractive. This 52-year-old tall ship, modeled after a late-1800s cargo schooner, docks steps from New London’s train station, so even carless city dwellers have no excuse for staying ashore. New London, CT. 800-697-8420; mysticwhalercruises.com

Whistling Man Schooner Co.

Winds are moody on Lake Champlain, and that makes sailing a challenge and a treat for captain Hannah Langsdale and her crew. Langsdale owns Friend Ship, a replica of a 1901 lobstering sloop, which departs two to five times daily for private charters and two-hour public tours on New England’s most lore-rich lake. Dangle your feet in the water and listen to tales of battles fought on Champlain before, during, and after the American Revolution. Never mind that a rumored sea monster lurks beneath the surface: You’ll feel carefree and inspired, especially late in the day, when the sun sinks behind the Adirondacks, turning clouds into wisps of ruddy-purple fire. Burlington, VT. ​802-825-7245; whistlingman.com