Water Activities in Gloucester, MA

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

Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

Paddle Beverly Harbor and Salem Sound at your own pace

Explore Beverly Harbor and Salem Sound at your own pace

Sail Boston Harbor and enjoy freshly shucked oysters onboard

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

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

Sail Boston Harbor at sunset on a classic schooner

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

Customize a private fishing or whale watch charter on a 70–90 ft boat

Customize a private fishing charter for up to 6 people

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

Take Your Turn Fighting Bluefin in a Crew-Led Rotation

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

Build confidence on the water with personalized paddling instruction

Build paddling skills with private instruction tailored to your experience

Paddle Lake Massapoag at your own pace

Cruise Boston Harbor for views of the tall ships on a classic schooner

Target Haddock and Pollack, With a Nearshore Backup Plan

Sail Boston Harbor at sunset for views of the tall ships and skyline lights

Paddle Lake Massapoag at your own pace in a single kayak

Paddle the Hampton Seabrook Estuary and add a fishing adventure

Paddle Lake Massapoag at your own pace in a canoe