things to do in Brewster, MA

Meet ghostly hosts with Revolutionary War stories to tell

See Cape Cod Bay's low-tide sands by fat bike

Private 3-hour morning bay cruise for up to 6

Fish Cape Cod waters on a 4.5-hour private charter for up to 6

Book a private whale watch to Stellwagen Bank in Provincetown

Share a whale watch trip from Provincetown and split the boat with other travelers

Rent a 2-person kayak for 24 hours to 1 month

Take in the dunes from an open-air Ford Bronco

Set your own course across Popponesset Bay

Seasonal tastings and local tales on a relaxed walk through Chatham

Sail Provincetown at sunset on the historic Schooner Hindu

Charter a private boat for Pleasant Bay’s Fourth of July fireworks

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

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

Sail Wellfleet Harbor on a private 3-hour charter, with tide-based stops for swimming or beach time

See Monomoy seals up close on a small-group harbor cruise

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Uncover exhibit details you might miss on your own

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

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

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

Take the helm with fishing-ready features and quiet Suzuki power

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Cruise Chatham Harbor privately and watch for seals with your group