Sailing in Malden

Select Local Merchants

From the hallowed field at Fenway Park to the educational havens of Harvard and M.I.T, Boston's history is written across its skyline. The area's nearby waterways allow for mostly unencumbered views of these sights, and guided boat tours let sightseers experience the city in a relaxing way. To this end, Charles Riverboat Company's vessels embark on journeys across the Charles River and Boston Harbor. Architecture tours guided by an expert from Boston by Foot and run together with BSA Space, Boston?s premier cultural institution on architecture and design, and home to the Boston Society of Architects, the tour's captains and crews point out historic sights such as famous buildings or the 100-story kettle used during the Boston Tea Party. Sunset tours offered under the warm glow of the setting sun wind through the river as music plays. Charles Riverboat Company also charters their boats for groups of up to 150.

100 Cambridgeside Pl.
Cambridge,
MA
US

Gray-hulled naval ships sit stoically by weathered docks, as sailboats and yachts dart to and fro in graceful traffic. The tide ebbs and flows around islands, piers, and against harbor walls under the Boston skyline. Hestia Cruises' four ships glide among this nautical throng, carving wakes across the busy waters on seasonal cruises in the morning, afternoon, at sunset, or under the light of the moon. As the classic 1948 motor yacht Full Moon rumbles through the water, on-board tour guides divulge facts about harbor history and point out ideal landmarks to photograph. The ship's open decks host passengers for sightseeing tours, and its staff also guides morning cruises with massage services or yoga classes, evening voyages with wine and whiskey tastings, and photo-shoot cruises.

Captains also ferry visitors past harbor sights on an EPA-acclaimed private catamaran or the 32-foot Catalina sailboat Hestia, where passengers can help pull lines, unfurl the main sail, and make a mix-tape of sea shanties. They also pilot a rigid inflatable boat—built to Navy Seal specifications—for adventures to far ends of the harbor at speeds of up to 40 miles per hour. The speedy craft lies low to the water, letting passengers feel the harbor's salty spray while hunched securely on saddle-style jockey seats.

269 Commercial Street
Boston,
MA
US

RIB Adventure Tours conduct informative history tours and scavenger hunts around Baltimore Harbor, even when the horizon becomes a blur; all tours take place aboard 26-foot-long rigid, inflatable speedboats. Built to Navy SEAL specifications by a local Massachusetts boat manufacturer, the boats keep riders secure aboard jockey seats. On guided history tours, passengers snag high-speed glimpses of harbor landmarks including lighthouses and forts, whose history guides can expound upon. During scavenger hunts, guides prompt passengers to look for environmental clues and give individual scores. Captains and tour guides brief passengers on safety before all excursions and supply them with high-grade waterproof cameras to take pictures of passing scenery.

More relaxed cruises from partner Hestia Cruises, onboard the 32-foot sailing yacht Hestia, might drift past the USS Constitution or out into the outer harbor. The ship is manned by a captain, a full crew, and friendly cocker spaniel named Ensign. Guests can help with the sailing duties, but padded seats and a BYOB policy for those of age may encourage them to sit back and relax.

269 Commercial Street
Boston,
MA
US

Head instructor Francois Asselin has guided Boston Sailing Center's neophytes to seaworthiness for more than 15 years, with his programs reaching more than 400 students annually. Mr. Asselin and his cadre of nine other sailing instructors take small groups onto the water to provide hands-on experience with the ropes, sails, steering, and maintenance of sailboats. Together, they introduce the science of seamanship or sharpen the skills of experienced sailors so they can eventually set sail on their own with a complete mastery over wind, water, and doing jumping jacks with a peg leg.

Boston Sailing Center owns an armada of vessels, which, in addition to lessons, may be rented for on-the-water events or lent out to members for regular sailing. Skippers conduct tours of Boston Harbor's skyline, stopping at scenic islands for impromptu picnics or to let parents maroon angst-ridden teenagers.

54 Lewis Wharf
Boston,
MA
US

Docked adjacent to the New England Aquarium, the Liberty Star and the Liberty Clipper look distinguished. The Liberty Star measures 67 feet long and can hold up to 39 passengers, and the Liberty Clipper measures 125 feet long with a capacity for up to 100 passengers. The massive schooner is an authentic replica of an 18th-century Baltimore clipper ship, thoroughly modernized to transport passengers on Boston Harbor sails and longer private charters. They sail daily throughout the harbor for public and group outings, along with private charters for special events, such as weddings or corporate proms. For a longer respite, they hoist the sails and steer southwards where the Liberty Clipper sails the Bahamas and the Liberty Star sails the Virgin Islands on adventure sailing vacations.

67 Long Wharf
Boston,
MA
US

A lifelong sailor and USCG Licensed Master, Captain Don helms his business, Come Sail Away Now, with the same seafaring sagacity he once employed as a commercial fisherman. His faithful ship, the Tupelo Honey, is a 31-foot replica of the 1904 sloop Dictator, one of the original ships that hunted for lobster on the coast of Maine. The captain invites passengers aboard for maritime services that range from private charters and public harbor cruises to sailing lessons. Each excursion unveils beautiful views of the city skyline only seen from the vantage point of Boston Harbor, a picturesque sweep that pairs well with wine tastings, morning brunches, BYOB cruises, and nibbling crackers to resemble the buildings of the Financial District.

1 Marina Park Dr.
Boston,
MA
US