48 hours on Shelter Island

Bike to beaches, hike in a nature preserve, and dine on fresh oysters and clams.

Located just 90 miles east of New York City, Shelter Island seems a world away. Made up of pristine beaches, wildlife sanctuaries, and hiking trails, a relaxed vibe is at its core. It's accessible only by ferry from Long Island's North and South Forks, heightening its secluded feel. Here's how to spend two days on this idyllic island.


Housed in a historic Victorian building, The Chequit has the ambiance of a bed and breakfast, but with a modern approach. Consider booking the Terrace Suite for private roof terrace access and an in-room claw foot tub.


Start your day on The Chequit's wraparound porch with a mug of coffee and a breakfast of homemade granola, yogurt, and seasonal fruit or a vegetable frittata.

Choose Your Afternoon Adventure

havens house


Explore the intriguing history of Havens House, originally a homestead built in 1743 on 1,000 acres. It's now home to over 50,000 historical maps, diaries, letters, photos, and other documents. Events are hosted throughout the summer and early fall season, including garden walks and car shows featuring collectable vintage cars. There's a farmer's market on the grounds where you can pick up lunch provisions such as local cheeses, artisan bread, salads, and olive oil.



Spend the day on the water with a guided paddleboarding tour with Venture Out, located on Crescent Beach, adjacent to The Sunset Beach Hotel. They'll take you through the creeks of Shelter Island, all the while teaching you about the history of the land. Alternatively, sign up for a paddleboard yoga class. Afterwards, enjoy a late brunch at Red Maple. Try the herb-roasted chicken or the shaved apple and fennel salad with the protein of your choice.

If you have time and energy after lunch, rent bikes from Piccozzi's Bike Shop. Or, for a bit of wildlife exploration, book an afternoon with Shelter Island Kayak Tour Company and kayak along the edges of the Mashomack Nature Preserve (which covers a third of the island), home to over 200 bird species, painted turtles, and nesting osprey.

For dinner, make a reservation at Sunset Beach. The menu boasts fresh seafood from dayboat fisherman and produce from local organic farmers. Order clams from the raw bar, the citrus-endive salad, and the poached Montauk striped bass with steamed vegetables and aioli. After dinner, stay for a game of ping pong, gather around the firepit, or watch the boats come and go from the two-story terrace.

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Grab a cup of coffee to go, along with a beach picnic, from The Chequit's adjacent White Hill Café. Or, head into Marie Eiffel Market, a grocery, juice bar, and café, for an organic kale and turkey omelet and a kale, carrot, ginger, and celery juice.

Choose your Afternoon Adventure



Visit Sylvester Manor Educational Farm where they teach about the importance of food and the culture and community surrounding it. Attend an event like the windmill cocktail party, held on the lawn under the Shelter Island windmill, or a workshop to better understand the farm's architectural and agricultural systems. Afterwards, enjoy the watermelon and arugula salad at The Rams Head Inn.

country club


Schedule an early tee time at Goat Hill, Shelter Island Country Club's public nine-hole golf course with over 2,512 yards of varying landscape that provides scenic views. For lunch, get the spinach and mushroom salad with freshly grated parmesan at The Flying Goat Restaurant at the club, situated on the highest point of the island.

After you re-fuel, make your way to Mashomack Preserve. Choose from one of the five trails, ranging from an easy one-miler to a 10-mile trek. Post-hike, head over to Shelter Island Craft Brewery for a beer flight or wine on tap. Relax on the outside picnic benches with a game of cards or darts.

Enjoy pre-dinner appetizers, such as fresh oysters, clams, and crab, at SALT Waterfront Bar and Grill. Then move over to 18 Bay Restaurant. Their four-course Italian-inspired Chef's menu changes every week. Toast to a well-spent 48 hours with a handcrafted cocktail or glass of local wine.