Best 175 things to do in East Dennis, MA

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

Reserve your kayak online and enjoy a full day on the water with included gear and basic instruction

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

Paddle from State Beach with a quick lesson and gear included

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

Schedule island-wide kayak delivery and pick up

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

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

Paddle Sengekontacket Pond with a private guide tailored to your group

Fish Cape Cod Bay on a private 4-hour charter for up to 6 people

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

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

Visit with lights off, muted videos, and reduced capacity

Shark-themed story time with sing-along and craft at Shark Center Chatham

Paddle Scorton Creek and create your own blown-glass piece

Connect with fellow explorers on guided Cape Cod outings

Set your own course for a private outing on the water

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

Taste Truro Vineyards wines and spirits aboard a historic schooner

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