things to do in Shelter Island Heights, NY

Build your paddling confidence with one-on-one attention

Find your fit with beginner and intermediate paddleboards

Raise the sails or simply relax on a private day afloat

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

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

Explore the Hamptons at your own pace on a lightweight, comfortable bike

Find your balance on the water with a dedicated yoga instructor

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

Explore Hamptons beaches and backroads at your own pace

Explore with a thinner-tire commuter e-bike built for longer rides

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

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

Explore on a step-through e-bike with speeds up to 25 mph

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

Set your proposal to your own soundtrack

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

Tackle rougher terrain with fat tires and electric power

Walk Mystic’s Water Street on a ghost pub crawl with three beer tastings

A guided social night of pizza, drinks and downtown Mystic bars

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

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