Water Activities in Brookline, MA

Ride a tiki boat for skyline views and a full-service bar on Boston Harbor

Sunset skyline views and harbor landmarks aboard a classic-style power yacht

Soak at your temperature with Boston skyline views and plane watching

Paddle Lake Cochituate with a single kayak rental in Natick

Cruise Boston Harbor on a 1.5- or 2-hour schooner day sail

Take the helm or relax aboard a historic wooden schooner

Charter a private yacht and cruise Boston’s waterfront with your group

Rent a stand-up paddleboard for a calm paddle on Lake Cochituate

Watch the Boston skyline at twilight on a 2-hour tall ship sail

Private Boston Harbor yacht cruise for celebrations and relaxed time on the water

Cruise Salem Harbor quietly with your own group and a licensed captain

Take in Boston's waterfront from a sailboat reserved for your group

Book a private tiki boat cruise for your group in Boston Harbor

Watch Boston’s skyline and the USS Constitution glow from the water at sunset

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

Cruise Boston Harbor on a private tiki boat for your group

Charter a 50-foot yacht for your private Boston Harbor cruise

Cruise Boston Harbor on Northern Lights with skyline views and captain commentary

Sail Boston Harbor at sunset on an 80-foot schooner

Pedal across Lake Cochituate with 1–4 hour rental options

Paddle Lake Cochituate in a stable canoe built for easy exploration

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

Take the helm and discover sailing aboard a traditional cutter ketch