Water Activities in Shelter Island, NY

Cast off on a private fishing trip aboard the Sunbeam VI

Enjoy four ways to ride, from wake-surfing to inflatables

Cast a line with bait, tackle, and fish cleaning included

Build your paddling confidence with your own group

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

Fish for blackfish with a stable ride and room to relax on board

Raise the sails or simply relax on a private day afloat

See Montauk's iconic lighthouse up close from the water

Shape your own Hamptons cruise with music, sandbar time, and coastal views

Unwind on deck with paddle boards and pool toys on hand

Enjoy a private cruise with your own picnic and drinks

Make Montauk your playground for watersports or a leisurely cruise

Drift reef structure for bottom fish with bait included

Turn sunset into an active outing with friends and family

Drift-fish reef waters at sunset and keep your catch

Combine fishing with panoramic views from the flybridge

Cruise waterfront coves and pause for an island swim

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

Enjoy a private cruise with your own food and drinks

A spacious deck for cruising and watersports

Kid-focused reef fishing with bait included

Fish from an extra-wide platform built for added stability

Drift reef waters for fluke with bait included and your catch to keep

Take the controls and ride beyond Montauk's jetty