things to do in East Dennis, MA

Cruise Oak Bluffs waters on a Yamaha WaveRunner with professional instruction

Sail Provincetown at sunset on the historic Schooner Hindu

Paddle into a Cape Cod sunset with an ACA-certified guide

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

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Paddle a clear-bottom kayak at night with glow lights on State Beach

Ski, wakeboard, kneeboard, or tube with professional instruction

Learn paddleboarding basics 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

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Learn sailing fundamentals with private on-water instruction

Try four tow sports with professional instruction on the water

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

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

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

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

Explore Shark Alley by private motorboat with expert guidance and aerial spotting

Explore Martha’s Vineyard waters aboard a private 38-foot Fountain charter