Water Activities in South Dennis, MA

Set sail on a private classic sloop tailored to your group

Fish Cape Cod waters for bass and tuna on an 11-hour private charter

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Learn to fly above the water by eFoil, kite, wing, or boat

Raise the sails or take the wheel on Martha's Vineyard waters

Ski, wakeboard, kneeboard, or tube with professional instruction

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

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

Cruise Chatham Harbor privately and watch for seals with your group

Enjoy a carefree day on the beach while we handle all setup, gear, and cleanup

Tour an oyster farm by boat and enjoy freshly shucked oysters

Share an evening harbor sail as the light shifts over the water

8-hour private haddock and pollock fishing charter for up to 6 people

Private whale watch with a sunset cruise in Provincetown Harbor

See Nantucket's harbor from the water with ice cream for everyone

Ride together for a captain-guided tubing adventure on the water

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

Try four tow sports with professional instruction on the water

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

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

Share a private motorboat cruise as evening settles over the harbor

Explore Sengekontacket Pond from State Beach with stable kayaks and a quick on-water intro

Take the helm of a Rhodes 19 sailboat