Water Activities in Fairfield, CT

See the Thimble Islands from open decks with live narration

Explore island history and local legends from the water

Cruise the bay at sunset and spot local wildlife

Enjoy patient fishing instruction and the comfort of a stable boat

Build sailing skills with a private lesson tailored to your goals

Relax on a 4-hour bay cruise with chances to spot local wildlife

Private sunset cruise with space for your food, drinks, and playlist

Cruise around the bay and watch for local wildlife

Cruise the bay for 2 hours and look for dolphins and other local wildlife

Soar above Fire Island on a Patchogue parasailing adventure

Cruise Oyster Bay Harbor as the sun sets

Help raise the sails or take the helm aboard a traditional tall ship

Sip cocktails and enjoy live music while cruising the Great South Bay

Paddle Oyster Bay’s protected waters in a stable tandem kayak

Sail into sunset aboard a traditionally rigged schooner

Build team racing skills and strategy on Long Island Sound

Customize your private IDA MAY fishing charter on the Long Island Sound

Charter the 60-foot Oyster Sloop CHRISTEEN for a private cruise

Charter the Ida May for a private sail with up to 44 guests

Build your sailing skills with instructor-guided time on Oyster Bay Harbor

Step aboard CHRISTEEN to see harbor sights and learn its story

Paddle protected Oyster Bay waters and explore the National Wildlife Refuge

Glide through Oyster Bay’s protected waters on a stable paddleboard

Build balance and paddling skills on Oyster Bay Harbor