Best results for Water Activities in Winthrop, MA

Pedal across Lake Cochituate with 1–4 hour rental options

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

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

Paddle Lake Massapoag at your own pace in a single kayak

Paddle Lake Massapoag at your own pace in a canoe

Sail historic harbor waters with maritime insights and optional hands-on sailing

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

Fish Gloucester’s banks with a seasoned captain and crew

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

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

Private yacht cruise for front-row Tall Ships views, up to 22 guests

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

Charter a 3-hour motor yacht for scheduled fireworks nights

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

Cruise Boston Harbor on a private yacht for Tall Ships views

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

Hands-on 1812-style sail with engaging crew and scenic Salem Sound views

Sail Salem Sound with your group of up to 40 and enjoy a private, hands-on experience

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

Reel in haddock and bring home your eligible catch

Bottom fish for haddock with bait and tackle included

Build sailing skills with a private instructor-led session

Take Your Turn Fighting Bluefin in a Crew-Led Rotation