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A North Ferry boat makes the approach to Shelter Island. (Credit: David Benthal)

A short ferry ride from Greenport, Shelter Island feels like a different place and time. Visitors can sit at the Shelter Island Pharmacy counter and the staff will cook them breakfast, find serenity hiking the tranquil coastline and unwind at cozy inns full of understated sophistication.

“[The rest of Long Island] is hustle-and-bustle, get the kids to school, go to work,” said Christine Beckwith, a Douglas Elliman agent and interior designer who grew up on Shelter Island. “Shelter Island is just like ‘ahhh.’ It’s just a completely different feeling.”

Beckwith is a local, but for those who aren’t, she shared her favorite places to eat, stay and play during a weekend on Shelter Island.


For breakfast and lunch, Beckwith said there’s a pair of restaurants with food and service so nice, they’re worth going twice. To sit down and smell the coffee, try The Islander, a brown-shingled eatery that looks and feels more like a home than a restaurant. In the Heights area, Stars Cafe is an ideal place for grab-and-go before hitting the beach. Both restaurants serve up classic continental fare. Think: eggs, fruit and pastries for breakfast and wraps, fries and salads for lunch.

As the clock inches towards dinnertime, it’s worth pulling toes out of the sand and taking in some of the notable restaurants the island has to offer. Salt Waterfront Bar & Grill, which has indoor or outdoor seating, offers a lively atmosphere and views to write home about. As for the menu, it’s a seafaring odyssey full of both classic and creative choices. There’s everything from fish and chips to trendy poke bowls to a lobster roll that even makes New Englanders swoon.

For an upscale affair, try Vine Street Cafe, a country-style restaurant so popular it doesn’t have an offseason. “They’ve been busy all summer and winter long, which is unheard of,” Beckwith said. The white tablecloths and candlelight make it ideal for treating that special someone — Beckwith and her husband have been known to come for a date night. She can’t get enough of the pan roasted filet mignon au Poivre made with green peppercorn sauce. “It’s so thick and juicy and the green peppercorn sauce they put on it is a hint of hotness but not too much,” she said. Reservations are a must.


Though Shelter Island is a worthy day-trip destination, visitors looking to linger have a bevy of accommodation options. Those coming from the North Fork find The Chequit especially convenient. “You can basically walk to it when you get off the North ferry,” Beckwith said. And since it’s in the Heights area, guests have easy access to the ample number of shops and eateries. Be sure to say the name right: CHEEK-wit. “[It’s] really funny how [people visiting] pronounce the name,” Beckwith laughed. “You know if you’re local or not.”

Steps from the ever-popular Crescent Beach, Shelter Island House has eight rooms and a restaurant that might ring a bell for North Forkers. Caci opened a second location there this spring, and Beckwith gave the food her seal of approval after dining there with girlfriends. As for the accommodations, light colored walls, plush beds and white curtains feel just right for a summertime getaway. Ditto for the pool with a spacious patio.

As luxurious as the hotels are, those seeking more space and privacy might consider renting. Beckwith said there are multiple styles of homes from small cottages and 1900 Victorians to modern abodes. The range allows for a variety in price, from $200 per night to more than $2,000 per night. Though planning a weekend far in advance may be preferred, it isn’t required. “There are still rentals available,” she said. “You can get something last-minute.”


Though known for its slower pace and turn-of-last-century charm, a weekend on Shelter Island can be enjoyed at any age. At more than 2,000 acres, Mashomack Preserve takes up about a third of the island. Often referred to as the jewel of the Peconic, the preserve has trails ranging from 1.5 to 10 miles and is home to a host of wildlife. A big bonus: “[It gives you] mostly shade, so you can stay cooler during the summer months,” Beckwith said. Families with children scream for ice cream and a round of mini-golf at Whale’s Tale, and active travelers favor Shelter Island Kayak Tours. The tours allow visitors to “explore the ospreys, turtles, hawks and fish,” Beckwith said. Those seeking independence can rent a kayak or paddleboard instead. For the land-dwelling, Piccozzi’s Fuel & Bike Shop rents bikes, something Beckwith has noticed is becoming more popular with weekenders.

And of course, visitors flock to Shelter Island for a day or 30 at the beach. Crescent Beach, sometimes called Sunset Beach because of the nearby restaurant by the same name, draws the biggest crowds. “The water is calm, you don’t have to worry about a whole lot of ocean waves which is great for anyone who doesn’t want to be knocked around,” she said. For those looking for less of a scene, Wades Beach provides a quieter alternative. Pro tip: Get a parking pass at Town Hall. Otherwise, “it [costs] fortune to park,” Beckwith warned. Passes are $25 for daily, $50 weekly, $95 monthly and $230 seasonal and give access to all public beaches.