Best 69 things to do in East Dennis, MA

Rent a kayak or paddle board and explore Oak Bluffs from the water

Schedule island-wide kayak delivery and pick up

Build kayaking and paddleboard skills on a 4-day kids series at Sengekontacket Pond

Build paddling skills at any level with a private lesson

Rent a paddleboard for 24 hours at State Beach in Oak Bluffs

Paddle open-ocean routes to remote spots with guides on Martha’s Vineyard

Paddle at sunrise with breakfast and coffee included

Build kayak skills with guided games and exploration for kids

Start your day with a beginner-friendly paddle board fitness class

Rent a kayak or paddle board for 1–3 months with free delivery

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

Private 1-hour Shark Center tour with interactive exhibits and time to self-explore

7–8 hour white shark and whale expedition with onboard experts

Private 2.5–3 hour white shark charter with a spotter pilot and AWSC naturalist

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Charter a sailboat in Key West for up to 42 guests

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

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

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