Water Activities in Shelter Island Heights, NY

Sail San Diego at sunset on a private 3-hour cruise

Sail privately in San Diego Bay with drinks and snacks included

Fish for blackfish with bait, tackle, and catch cleaning included

Drift over reef structure in search of blackfish

Learn fishing techniques from an experienced crew

Combine fishing with panoramic views from the flybridge

Find your fit with kayak options for new and experienced paddlers

Build your paddling confidence with one-on-one attention

Help raise the sails or settle in for a relaxed family outing

Raise the sails or simply relax on a private day afloat

Find your fit with beginner and intermediate paddleboards

Enjoy your own picnic on the water with a choice of cruising routes

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

Shape your own outing with options to cruise, swim, or step ashore

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

Sail at your own pace, with room to explore or simply unwind

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

Pair a romantic evening on the water with hands-on sailing

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

See the Thimble Islands from open decks with live narration

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

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

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