Water Activities in Shelter Island, NY

Relax on a private sail with onboard comforts

Settle into a full day on the water

Sail privately in San Diego Bay with drinks and snacks included

Learn fishing techniques from an experienced crew

3-hour sunset sail on a 40-foot boat with drinks and snacks included

Find your fit with beginner and intermediate paddleboards

Lend a hand with the sails or simply relax as evening unfolds

Get out on the water with kayaks focused on accessibility and ease of use

Get out on the water with a board suited to beginner or intermediate paddling

See the Thimble Islands from open decks with live narration

Explore island history and local legends from the water

Captain your own boat on a guided 3-hour Mystic River ride

Join a shared drift-fishing trip aboard a 70-foot boat with bait included

Get a close-up look at an island lighthouse from the water

Cruise with a stocked tiki bar and room to dance

Share a tandem kayak or paddle on your own

Take in local sights from the water

Enjoy a private fishing trip with a lifelong angler and room to relax on board

Explore your way with comfortable paddling options or a bike ride around town

Spend golden hour on the open water

A customizable private boat outing with sandbar stops and coastal wildlife viewing

Sail beneath the Hunter's Moon on an autumn evening cruise

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

Captain your own boat for 1 hour on Fishers Island Sound