things to do in Shelter Island, NY

See the Thimble Islands from open decks with live narration

Explore island history and local legends from the water

Hear Mystic’s darker history, legends, and paranormal tales

Fish with Captain Keith, featured in The Fisherman Magazine

Explore dinosaur trails, caves, a maze, playgrounds, and a seasonal Splash Pad

Sail the San Diego coast at sunset with complimentary drinks and snacks

Cast off on a private fishing trip aboard the Sunbeam VI

Taste six curated stops on a guided walk through Mystic’s coastal dining scene

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

Book a 3-hour private bachelorette sail in San Diego, with daytime or sunset departures

Walk Mystic’s Whitehall Burial Ground on a history-and-ghost tour after dark

Cast off aboard a 42-foot boat for private fishing

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

Trace Mystic’s maritime past through landmarks and lesser-known waterfront stories

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

Follow a glowing dinosaur trail with family games, inflatables, and marshmallow roasting

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

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

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

Discover the art and coastal inspiration behind Mystic's creative community

Cruise waterfront coves and pause for an island swim

Sail privately in San Diego Bay with drinks and snacks included

Explore southeastern Connecticut wine country without planning or driving

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