Water Activities in Winthrop, MA

Set sail for a personalized tiki cruise through Boston Harbor

Celebrate aboard a spacious vessel with a ballroom, two bars, and crew support

Celebrate on the water with a ballroom, two bars, and dedicated crew

Introduce the family to deep-sea fishing with crew support for every age

Take the helm or relax aboard a historic wooden schooner

Turn your celebration into a private Boston harbor party

Cruise Boston Harbor on a 1.5-hour narrated history tour

Private sail for up to 6 guests beyond Marblehead Harbor

A private classic-yacht sail along the North Shore

Cruise Boston Harbor at sunset and watch the USS Constitution cannon fire

Paddle Lake Cochituate together in a sit-on-top tandem kayak

Explore Lake Cochituate with a sailboat rental for family-oriented time on the water

Harbor landmarks and a laid-back Tiki Boat morning

Private event yacht with a ballroom, two bars, and dedicated crew support

Private Boston Harbor outings with a captain, cooler, and bathroom

Fish Gloucester’s banks with a seasoned captain and crew

Sail Salem’s North Shore aboard a storied 1939 wooden schooner

Sip and take in Boston Harbor's golden-hour skyline

See fall foliage on a 1.5-hour Boston Harbor cruise with a gourmet picnic lunch

Private 4-hour sail from Marblehead Harbor for up to 6 guests

See Boston’s skyline light up from a lively tiki boat cruise

Cruise Boston Harbor and enjoy a fall brunch buffet aboard Northern Lights

Host large celebrations with a ballroom, two bars, and crew service

Fish beyond the usual day-trip range with 30% fewer people on board