Water Activities in Plymouth, MA

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Pick up a kayak or paddleboard at Lawrence Pond and explore at your own pace

Paddle Popponesset and Ockway bays at sunset with an ACA-certified guide

Paddle Cape Cod waters with gear delivered to your launch area

Explore Cape Cod waters with paddle gear delivered to your launch spot

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

2-hour Plymouth Harbor party cruise with DJ, onboard bar, and landmark views

Join a pirate crew mission with treasure maps and water cannons

Sail New Bedford Harbor and Buzzards Bay on a private charter

Sail close to the water on an interactive harbor charter

Celebrate on a private Plymouth Bay cruise with a flexible route and onboard comforts

Explore calm harbor waters with local guidance

Explore Stellwagen Bank’s whale feeding and nursing grounds by private boat

Paddle Cape Cod’s barrier beaches with an ACA-certified guide

Paddle into a Cape Cod sunset with an ACA-certified guide

End the day with a guided paddle as Cape Cod’s evening sky changes

A relaxed guided paddle with a midway ice cream boat stop

Cast, jig, and troll for striped bass and bluefish with crew support

Private charter to fish for striped bass and bluefish and look for whales

Haul lobster traps and meet Plymouth Harbor sea life in 1 hour 15 minutes

Build your own ice cream sundae on a 75-minute Plymouth harbor cruise

Private boat charter for up to six people

Private 3-hour beach cruise for up to six, with snacks and soft drinks included