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Ram’s Head Inn on Shelter Island. (Photo credit: Doug Young)

Be careful when you float on over to tiny Shelter Island; you might never want to leave. Since it was first dubbed Manhansack Aha Quash A Womack by its original Native American Manhanset residents, this “island sheltered by islands” has drawn people in for its wild, natural beauty, boating and biking lifestyle and leave-your-cares-at-the-ferry-line vibe. 

This is by no means an exhaustive list of what’s great about the Rock — but if you’re dipping a toe into a day or overnight visit of isle-awhile fun, here are a few solid suggestions for planning your island itinerary.  

Eat & Drink

Not to belabor the “best kept secret” trope, but low-key Kyle’s (27 North Ferry Road, 631-749-0579) fills that bill. Chef and owner Kyle Seddio’s lovely little restaurant and take-out bakery is open for breakfast and lunch, where she whips up a magical, soufflé-like frittata and house-made jelly donuts that will make you weep, they’re so damn good. 

Darryn Weinstein, owner of The Eccentric Bagel (25 West Neck Road, 631-749-5363), brought the very first made-fresh-daily versions of the breakfast staple to Shelter Island, and he’s beloved for his excellent classic and creative versions. Grab one with the schmear of your choice along with a cup of good coffee, and sit at one of the brightly colored picnic tables outside for a bite. 

A cocktail at Léon 1909. (Photo credit: Doug Young)

More often than not, you will find owner Valerie Mnuchin manning the host station of her excellent open-fire-cooking restaurant Léon 1909 (29 West Neck Road, 631-749-9123). It’s become a destination for both on- and off-islanders for its outstanding wine list, flame-licked dishes like the dreamy bone-in ribeye, house-made bread and inventive cocktails — and, of course, the fab fire show from the wall-wide wood-burning oven.

Year-round staple Vine Street Café (41 South Ferry Road, 631-749-3210) serves stellar, comforting cuisine that manages to feel both classic and energetic. The ever-excellent service here and expectation-meeting fare from owners Lisa and Terry Harwood keeps Vine Street hoppin’ (and packed — reservation making is the way to go!) nightly. 

Pizza, you say? The island has two solid options sure to please any way you slice ‘em. Frankie Venesina’s Shelter Island Slice (3 North Ferry Road, 631-749-9292) is the place to grab a namesake quick lunch or a full-on meal of wings, garlic knots and pies for the whole fam while you watch the game on the big screen TV or outside at their sweet alfresco tables (pizza pedigree alert: his parents owned beloved Conca D’Oro in Sag Harbor). For a more trattoria-like vibe, hit up Brad Kitkowski’s Isola (15 Grand Ave., 631-749-9036) for specialty, wood fired pizzas like the BPT (applewood bacon, hot cherry peppers and sun-dried tomatoes), classic Caesar salad and craveable and comforting pastas served in the historic 19th-century dining room that make you feel like you’ve wandered into nonna’s summer house.

Attached to a garden nursery, White Oak Wine Bar’s (2 Manwaring Road, 631-749-5814) serene, undulating outdoor sitting area feels like your own secret garden, with cheese plates from parked-on-premises King Reeve Cheese and wines made under the White Oak label by Lenz winemaker Tom Spotteck.

Blues and fish are the order of the day at island staple Commander Cody’s (41 Smith St., 631-749-1851), a no-frills, BYOB, last-of-its-kind fish shack run by owner and fisherman Jimmy Hayward and his Culinary Institute of America-trained chef daughter, Amanda Hayward. Satisfying fresh fish dishes are broiled or fried, and if you have the wherewithal to order ahead for Jimmy’s authentic Southern fried chicken and ribs, do it. It’s worth the wait. (And desserts are Amanda’s specialty; don’t pass ‘em up.)

A boaters’ paradise, Salt (63 Menantic Road, 631-749-5535) has a pull-up-your-Boston-Whaler, let-the-good-times-roll vibe. Poke bowls, fish tacos and lobster rolls will fill you up dockside, and steps-away rockin’ bar The Shipwreck is the place to be for live music all season long. 

Ice cream and summer? Heck yeah! Head to the Tuck Shop (75 North Menantic Road, 631-749-5939) for all your favorite flavors  (they make ice cream cakes too), or the Whale’s Tale (3 Ram Island Road, 631-749-1839) for a round of mini-golf and a cone or cup of your fave cool-down sweet treat. 

Shop

For a one-stop-strollable shopping experience, the Heights is where it’s at. The Shelter Island Pharmacy (19 Grand Ave., 631-749-0445) and Bliss’s Department Store (186 North Ferry Road, 631-749-0041) offer the best souvenir T-shirts in town, along with other island-centric take-homes, like coasters, fridge magnets and hats. For some serious well-curated clothing shopping, Pure Soul (183 North Ferry Road, 516-413-4136) has gorgeous linen dresses and tops, along with island-vibe purses, earrings and shoes, and Purethread (181 North Ferry Road, Suite C, 631-880-6420) provides a bespoke-but-friendly atelier experience. If you want to adorn your home as well as yourself, unique Ram Design Home (181 North Ferry Road, 631-749-5067) will grace your interiors with a non-Pottery Barn warmth and individual style.

And for a more under-the-radar (read: unique!) shopping stop, hit up K Studio (16. North Ferry Road), a sweet little shed in the center of town where Karen Springer brings a little handcrafted touch of Central and South America to island style, with woven bags, handmade jewelry and a multitude of other pretty surprises.

Play

At over 2,000 acres, Mashomack Preserve (79 South Ferry Road, 631-749-4219) offers six different trails offer varying distances and wheelchair- and stroller-accessible options through the woods and water-rimming routes in this natural island gem. 

With intriguing exhibits and robust Saturday farmers market, Shelter Island Historical Society (16 South Ferry Road, 631-749-0025) is the heart of the island’s well-preserved and curated history. And their excellent gift shop offers a multitude of locally made keepsakes well worth perusing.

Summer is baseball season! Island collegiate baseball team, the Bucks, will be representing Shelter Island in America’s favorite pastime against other local East End teams. Check the schedule (hamptonsbaseball.org) for home games at Fiske Field on Bateman Road. 

As part of the summer long workshop and residency programs attended by some of the country’s best young classical string musicians, the Perlman Music Program(73 Shore Road, 212-877-5045) offers free concerts for their Works in Progress performances. Guaranteed to take your breath away; check perlmanmusicprogram.org for this summer’s schedule. 

Stay

With 37 rooms divided between the main 1872 building and nearby off-premises abodes, The Chequit (23 Grand Ave., 631-749-0018) is a stylish spot to decamp in the heart of the Heights, with breakfast-to-dinner dining and a friendly downstairs pub that’s popular with both locals and visitors alike. 

You can’t beat the sunset views from the bay-fronting lawn or second-floor deck of The Pridwin Hotel & Cottages (81 Shore Road, 631-749-0476). But any time of day, this circa 1927 summery vibe spot always feels like the place to be, whether dining at the fresh-focused Terrace restaurant and bar, poolside lounging or hitting the full-service in-house spa.

The Ram’s Head Inn (108 South Ram Island Dr., 631-749-0811) feels like something out of a storybook, with its pretty cedar-shingled  exterior, Adirondack chair-dotted lawn facing Coecles Harbor and tucked-away location. Old-timey yard games, unrushed vibes and an excellent on-premise restaurant make this female-owned inn feel like the ultimate escape. 

(Photo credit: Doug Young)

Billed as a bed-and-breakfast, Seven (7 Stearns Point Road) is a bit more stylish than your typical country biscuits-and-tea haven. Just up the hill from popular Crescent Beach, it offers an in-ground pool and croquet matches on the lawn. You can even get your breakfast delivered to your room in a sweet little wicker picnic basket.  

For an idyllic B&B experience,  look to the House on Chase Creek (3 Locust Ave.,  631-559-2296). Proprietor Bill Cumming’s four-room, lovely respite, each with private bathrooms. Its Heights location is also a convenient jumping off point for restaurants, shopping and renting bikes at Piccozzi’s gas station (177 North Ferry Road, 631-749-0045).

An island staple for decades, the butter-yellow, nearly 200-year-old Candlelite Inn (3 South Ferry Road, 631-834-7578) has stood the test of time. Owned by islander John Sieni, this bed and breakfast is one of the more reasonably priced options on the island, with tidy, minimalist rooms and a quiet, wrap-around porch, perfect for a glass of iced tea or a little rosé at the end of a long day exploring. 

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