date published: August 14, 2006

Put new wind in your sails by enjoying some of Boston’s best maritime experiences
by Josh B. Wardrop

Boston is a traditionally seafaring community, and one only needs to look at Boston Harbor on a summer day to see that maritime spirit hasn’t changed much. Whenever fair skies and favorable winds allow, boat enthusiasts young and old can be found raising their sails and taking to the water for daytime sailing expeditions.

Liberty Fleet of Tall Ships has been a key figure on the Boston sail scene since 1992, ferrying guests along the coastline aboard the 125-foot schooner the Liberty Clipper. A typical two-hour jaunt aboard the Liberty Clipper—a replica of a mid-1800s Baltimore schooner that was originally built in Mystic, Conn.—takes visitors out to explore the Boston Harbor Islands, or perhaps offers a swing around the North End and the Charlestown Navy Yards.

And guests aboard the Clipper can either take the opportunity to relax and enjoy the sea breezes, or take a more active role in the sailing of the vessel, helping to hoist and raise the sails.

Standard sails depart three times daily, at noon, 3 and 6 p.m., from Long Wharf. However, Liberty Fleet also offers specialty cruises like Friday night steak and lobster sails, Sunday brunches and occasional wine tasting sails. And on weekends, the Clipper kicks it up a notch by inviting the Freedom Trail Players aboard to take visitors through a re-enactment of the Boston Tea Party—guests can help dump tea in the ocean while the ship’s captain orders the cannons to be fired. (Tea Party sails by reservation only—refer to listing)

If nautical warfare gets your heart pumping, you won’t want to miss your chance to hop aboard the tall ship Formidable, a brigantine vessel that sails from Waterboat Marina at Long Wharf. This tall ship raises its deep red, square-rigged sails and takes passengers on sailing excursions around Boston Harbor every Tuesday–Sunday. (Weekday sails are at 11 a.m., 1, 3 and 5 p.m.—but those first three times are often reserved for charity groups, so your best bet is likely to be at 5.)

It’s Saturday’s sails, though, that take the excitement to another level, as those trips (at 11 a.m. and 2 and 5 p.m.) see the Formidable become the victim of an “ambush” by the privateer Poincare. Become a part of the action as cannons blaze, flags fly, and your ship becomes part of a fantastic harbor battle re-enactment. All the fun of a battle at sea, and nobody has to walk the plank. Call 508-954-1282, or visit, for information and reservations.

Of course, the ultimate draw for any fan of naval military history also resides right here in Boston—the U.S.S. Constitution, which is moored at Charlestown Navy Yard. “Old Ironsides,” as she’s affectionately known, is the nation’s oldest commissioned warship, first launched on October 21, 1797. Visitors who make their way to Charlestown today can check out the U.S.S. Constitution Museum (refer to listing), which exhibits period weapons, sailors’ journals, uniforms and more. Or, climb aboard the ship herself for guided tours—from the decks to the gunports to the sailors’ quarters and beyond—which are led every half-hour.

Sometimes, the call of the sea is so strong that a seasoned sailor simply needs to hop aboard a boat and strike out on the water away from the cares and worries of life on the land—which is all well and good, but not always practical unless you can get access to a boat. Thankfully, that isn’t a problem on the Boston waterfront, as a bevy of charter options exist for sailing aficionados.

The Boston Harbor Sailing Club (Rowes Wharf, 617-720-0049) is primarily a member club that specializes in teaching novices how to sail and organizing outings for its members. However, the club also offers charters and rentals of its numerous sailing vessels (to appropriately credentialed sailors) when members aren’t using them. Fully outfitted daysailers, ocean racers and cruisers are available starting from as little as $90 per day.

Others offering charter services include the Boston Sailing Center (starting at $120 per hour, 2 hour minimum, 6 person maximum per boat, Lewis Wharf, 617-227-4198); Boston Yacht Charters (Seaport World Trade Center, Seaport Boulevard, 617-723-8810), who provide sailboats, schooners and larger yachts capable of carrying anywhere from 12–49 passengers; and Atlantic Charters (Village Street Dock and Commercial Street Dock, Marblehead, 781-639-0055), which offers voyages aboard the Friendship Sloop Resolute, the 25’ Catalina Amnesia and various other vessels, with trips beginning at $95 for four-hour rentals, and $295 for two-hour captained charters.

For landlubbers who have always been fascinated by the schooners and sloops of yore, but have never managed to get a sturdy set of sea legs under them, there are plenty of ways to enjoy New England’s maritime scene from sturdier ground.

If your appreciation of sailing is tied to a need for speed, you’ll want to head up the North Shore to the quaint seaside village of Rockport for the 2006 Rhodes 19 Class National Championship Regatta from August 22–25. The event, which takes place at the Sandy Bay Yacht Club, unites sailors from around the region in a series of short races just off the harbor. Find a good vantage point along Rockport Harbor to check out the races, then spend the day visiting the numerous local art galleries and antique shops.

Every summer for 24 years, vintage boat enthusiasts from around the country have brought their antique boats to Salem, one of Boston’s oldest maritime hotbeds, for the annual Antique & Classic Boat Festival at Hawthorne Cove Marina. Taking place August 19 & 20, the event allows sailing enthusiasts to swap stories with other collectors, talk shop and show off their fantail launches, yawls, schooners and yachts to the public. The festival features boat exhibitions, awards, a nautical parade and blessing of the fleet, crewmen in period costume and a general atmosphere of appreciation for these magnificent ships. And if you don’t have the wheels to head up to Salem, the city is accessible by MBTA commuter rail or via 40-minute catamaran rides departing from Aquarium Wharf (call 617-222-6999 for schedule information). Refer to listing.

Meanwhile, that same weekend, a bit further north in the traditional fishing port of Gloucester, the lovely harborside environs of Stage Fort Park play host to the 26th annual Gloucester Waterfront Festival. This annual arts and crafts-oriented festival brings together more than 175 artisans from around the country to display and sell items ranging from fine jewelry and pottery to birdhouses and music boxes. Combined with live musical entertainment, stilt-walkers, a vintage car show and more, it makes for a fun way to spend a day down by the ocean even if you don’t know port from starboard.

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