Water Activities in Brookline, MA

Set sail for a personalized tiki cruise through Boston Harbor

Step ashore on quiet harbor islands while your captain waits

Take in Boston Harbor’s history on a narrated midday cruise

Turn your celebration into a private Boston harbor party

Private sail for up to 6 guests beyond Marblehead Harbor

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

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

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

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

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

Harbor landmarks and a laid-back Tiki Boat morning

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

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

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

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

Private sailing with coastal views along Boston's North Shore

Private tiki cruise for celebrations on Boston Harbor

Celebrate on a private tiki boat cruise through Boston Harbor

Cruise the harbor for Sail Boston tall-ship views with narration

Paddle Salem’s historic coast with guided stories and coastal views

Cruise Boston Harbor with a gourmet brunch buffet and captain commentary

Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

Sail a 1930 schooner past Salem Sound lighthouses