things to do in Plymouth, MA

Sail Provincetown at sunset on the historic Schooner Hindu

Set your own course across Popponesset Bay

See Plymouth Harbor highlights with live narration from an expert crew

Celebrate with a private Plymouth Bay cruise tailored to your group

Paddle Cape Cod’s quiet marshes with guidance for every experience level

Take in Provincetown's dunes and sunset from a private open-air Bronco

Drift live and artificial baits in shark waters off Cape Cod

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Take to the harbor with just your own group

Sail New Bedford Harbor and Buzzards Bay on a private charter

Rent a canoe for 24 hours to 1 month and get on the water

Chase big game from July into late fall

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

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

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

Paddle Cape Cod waters with gear delivered to your launch area

Explore the Outer Cape's dunes, then unwind by the water at sunset

Search whale feeding grounds for a chance to spot several whale species

Private whale watch with a sunset cruise in Provincetown Harbor

Fish with a captain who has known Boston’s waters since childhood

Sail close to the water on an interactive harbor charter

Rent a stand-up paddleboard for 24 hours to 1 month

Target big game and take on strong-fighting striped bass