things to do in South Dennis, MA

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

Set sail on a private classic sloop tailored to your group

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

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

Enjoy a private evening cruise past Provincetown’s historic lighthouses

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

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

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Ski, wakeboard, kneeboard, or tube with professional instruction

Try four tow sports with professional instruction on the water

Learn paddleboarding basics with an ACA certified guide

Paddle Cape Cod waters with gear delivered to your launch area

Learn sailing fundamentals with private on-water instruction

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

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

Paddle Popponesset Bay at your own pace with included gear

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

Private whale watch with a sunset cruise in Provincetown Harbor

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

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

Learn stand-up paddleboarding with a guided, beginner-friendly tour

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

Private family kayak lesson with ACA (American Canoe Association) certified guides

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