Best results for Water Activities in East Dennis, MA

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

Learn sailing fundamentals with private on-water instruction

Share a sunset motorboat ride through the harbor

Sip, Savor & Cruise: Narrated Harbor Views with Cocktails and Ice Cream Treats Onboard

Hunt for treasure with a pirate crew at sea

Private 3-hour morning bay cruise for up to 6

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

Paddle Popponesset Bay at sunset and into the full moonlight

Paddle through a clue-filled pirate quest with a water cannon showdown

Private 3-hour beach cruise for up to six, with snacks and soft drinks included

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

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

Soar up to 600 feet over the sea on a parasailing flight

Cruise Oak Bluffs waters on a Yamaha WaveRunner with professional instruction

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