Water Activities in Winthrop, 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

Join the crew for hands-on giant bluefin tuna fishing

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

Sail a 1930 schooner past Salem Sound lighthouses

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

Look for whales on a cruise to Stellwagen Bank

Cruise to Stellwagen Bank on a narrated 3–4 hour whale watch

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

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

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

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

Make Salem Sound your private escape aboard a classic schooner

Cruise Boston Harbor on a private tiki boat for your group

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

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

Sunset sailing aboard John Alden's racing yacht

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