Best 279 things to do in Gloucester, MA

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

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

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

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

Private event yacht with a ballroom, two bars, and dedicated crew support

Private Boston Harbor outings with a captain, cooler, and bathroom

Host large celebrations with a ballroom, two bars, and crew service

Take Your Turn Fighting Bluefin in a Crew-Led Rotation

Sail into the sunset with live Celtic tunes and sea shanties

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

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

Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

Reel in haddock and bring home your eligible catch

Chase giant bluefin tuna on a hands-on offshore fishing trip

Battle New England sharks on light tackle

Join the crew for hands-on giant bluefin tuna fishing

Bottom fish for haddock with bait and tackle included

Paddle Salem Harbor at your own pace from Salem Willows Park

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

Paddle Salem Harbor your way with flexible kayak rentals

Paddle Beverly Harbor and Salem Sound at your own pace

Explore Beverly Harbor and Salem Sound at your own pace

Build confidence on the water with personalized paddling instruction