things to do in Dennis, MA

Share a Chatham Harbor motorboat cruise and look for seals

Soar up to 600 feet over the sea on a parasailing flight

Set your own course across Popponesset Bay

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

Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group

More room at the rail on a fishing-first charter

Rent a kayak or paddleboard and explore State Beach from the water

Private 3-hour morning bay cruise for up to 6

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

Fish for sharks off Cape Cod on an 8-hour private charter

Book a private whale watch to Stellwagen Bank in Provincetown

Sail Provincetown at sunset on the historic Schooner Hindu

See Plymouth Harbor highlights with live narration from an expert crew

Cruise Oak Bluffs waters on a Yamaha WaveRunner with professional instruction

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

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

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

Ski, wakeboard, kneeboard, or tube with professional instruction

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

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

Paddle Cape Cod waters with gear delivered to your launch area

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

Cruise Wellfleet Harbor at sunset on a private charter for up to 6

Fish Cape Cod waters on a private 8-hour charter for up to 6 people