Sailing in Jamaica Plain


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  • Boating in Boston
    Boating in Boston drops oars in seven locations?including local lakes, ponds, the Charles River, and Boston Harbor?sending visitors on watery adventures with a fleet of canoes, kayaks, sailboats, pedal boats, paddleboards, and festive and essential lifejackets. Whether navigating the peaceful waters of Hopkinton State Park's Hopkinton Reservoir?the place that, in 2002, started it all?or campus-adjacent eddies of UMass Boston's Fox Point Landing, visitors can hit the water untrained or sharpen skills with solo or group lessons. The crew of instructors also instills a love of boating in the littlest landlubbers with youth summer camps that teach basic skills and safety.
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    100 William T Morrissey Boulevard
    Boston, MA US
  • Hestia
    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.
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    269 Commercial Street
    Boston, MA US
  • Boston's Best Cruises
    As the sun makes its retreat into the horizon, the whales of Stellwagen Bank National Marine Sanctuary come out to play. Their elephantine fins slap the waters with such zeal that the pod seems to be putting on a performance for the catamaran of whale watchers in their midst. This end-of-day nature show experienced by passengers aboard Boston's Best Cruises’ New England Aquarium Whale Watch is hardly a rarity, as the ship’s crews guarantee sightings of these gentle giants with each excursion. Champions of the natural beauty of Boston Harbor and the area’s rich maritime history, Boston's Best Cruises’ expert crew sets sail on cruises to suit all manner of interest. Along with their whale watches, Boston’s Best Cruises whisks passengers away on Harbor Cruises that grant unimpeded views of the Boston skyline and the King Kongs pumping fists within its skyscrapers. The Salem Ferry facilitates leisurely cruises between Boston and the historic city, and aquatic outings to the Boston Harbor Islands National Recreation Area enable activities such as sunset clambakes, hiking, and fishing.
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    Long Wharf
    Boston, MA US
  • RIB Adventure Tours
    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.
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    269 Commercial Street
    Boston, MA US
  • Liberty Fleet of Tall Ships
    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.
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    67 Long Wharf
    Boston, MA US
  • Boston Harbor Cruises
    At the age of 16, Matthew "Matty" Hughes became the youngest-ever licensed captain in the port of Boston. Funneling his passion into a career, he founded Boston Harbor Cruises in 1926 to lead tours up the Charles River. What began as a two-man, one-boat operation has grown tremendously throughout its more than 90-year history, now encompassing a 21-boat fleet and more than 250 employees who transport more than 2 million passengers. The Boston Harbor Cruises's staff handles all things nautical, from whale watching and speedboat tours to wedding receptions and celebrations for special occasions. Because dolphins are hard to saddle and refuse to obey verbal commands, Boston Harbor Cruises also navigates the waters with ferries and harbor cruises that explore the historic and romantic sights of Boston. Though the leadership has changed, Matty's grandchildren Rick and Chris Nolan still perpetuate the traditions of Boston Harbor Cruises, furthering one man's obsession with the harbor and inspiring future generations to create their own memories on its calm waters.
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    63 Long Wharf
    Boston, MA US

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