Water Activities in Winthrop, MA

Paddle the Charles River with a kayak suited to beginners and seasoned paddlers

Sail Boston Harbor on the Liberty Star tall ship in 1.5 hours

Paddle Salem Harbor at your own pace from Salem Willows Park

Charter a 3-hour motor yacht for scheduled fireworks nights

Private schooner sailing with captain and crew included

Battle New England sharks on light tackle

Raise the sails and sip mimosas aboard a classic yacht on Salem Sound

Sail into the sunset with live Celtic tunes and sea shanties

Holiday jazz, cocoa, and harbor lights aboard a festive power yacht

Bottom fish for haddock with bait and tackle included

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

Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options

Experience a calm private winter paddle with dry suits and an expert guide on sheltered New England waters

Charter Motor Yacht Atlas for a 3-hour fireworks cruise for up to 25

Paddle Salem’s coast at dusk with beginner-friendly guidance

Cruise Boston Harbor on a private yacht for Tall Ships views

Share a relaxed paddle through the Charles River at Nahanton Park

Sail Boston Harbor at sunset on a classic schooner

See visiting schooners up close during Gloucester's Heritage Day celebration

Photograph visiting schooners as they arrive for Gloucester’s festival weekend

Paddle the Charles River through Nahanton Park’s quiet channels and wetlands

Sail Boston Harbor with stories, skyline views, and complimentary pastries

Take Your Turn Fighting Bluefin in a Crew-Led Rotation

Paddle Lake Massapoag together in a stable sit-on-top kayak