Often known as the ‘un-Hamptons,’ this small island between Long Island’s north and south forks leaves pretension on the mainland. Instead, it’s a place of natural beauty – mostly found at its numerous beaches and freshwater ponds and in the Mashomack Preserve and Coecles Harbor Marine Water Trail. Still, there are also stylish shops, cute cafés, and even a chic beach club where you can sip cocktails at sunset. So, if you’re planning on taking the 10-minute ferry ride to Shelter Island, here’s how to spend the perfect weekend there.
DAY ONE
Where to stay
Sprawled on 10 acres of land along Peconic Bay, the family-owned Pridwin Hotel & Cottages makes a great weekend base. Despite being almost 100 years old, a major facelift two years ago made it fit for the 21st century – the main house now has 33 stylish rooms with brushed oak king beds, and there are an additional 16 stand-alone cottages surrounding a heated pool. It’s also home to a tasteful sundries shop (Edie’s), a vintage game room, and a fitness centre and spa, plus a restaurant overlooking the beach and the horseshoe-shaped Crescent Bay.
Bagels, bikes, and beaches
Start your day at Eccentric Bagel Shop – its ’90s-inspired décor is sure to bring a smile to your face. Join the line of locals and visitors who are all waiting to order fresh bagels filled with a variety of intriguing flavours – like egg, za’atar, and jalapeño cheddar, topped with the likes of sriracha cream cheese, lox, scrambled eggs, and avocado.
Next, head to one of the island’s uncrowded beaches, ideally by bicycle – which you can rent at Piccozzi’s Bike Shop if you haven’t brought your own. Trundle down the unpaved Oak Tree Lane until you see the narrow curl of shoreline that makes up Shell Beach, or, if it’s views of Gardiners Bay and Bug Light lighthouse you’re after, make your way to Hay Beach. And if you’ve got kids in tow, Wades Beach is ideal, thanks to its calm waters, comfort stations, and lifeguards – plus, if you need a refreshment, simply duck into the family-owned Tuck Shop for ice cream and frozen yoghurt.
Hike, paddle, and kayak
If it’s not too hot, set out on a hike in the 2,039-acre Mashomack Preserve, where you can explore tidal creeks, woodlands, salt marshes, freshwater wetlands, and 12 miles of coastline. Or, paddle the five-mile round trip Coecles Harbor Marine Water Trail with Shelter Island Kayak Tours; you can either take a guided tour or rent your own kayak or paddleboard. Keep your eyes peeled: fiddler crabs, diamondback terrapins, blue herons, egrets, and osprey all call this place home.
End the day with dinner at Leon 1909, a new(ish) restaurant in an airy, farmhouse-style wood structure with an open hearth. Its seasonal, French- and Italian-inspired dishes are all cooked over an open flame – but make sure you save room for the blueberry panna cotta or olive oil cake (or both, we won’t tell).
DAY TWO
Relocate to Rams Head
Drive or bike to the northeastern tip of the island, which features outcroppings known as Little Ram Island and Big Ram Island. There, you’ll find Rams Head Inn, another historic hotel (this one is more than 100 years old) with a sprawling lawn leading down to the water. The lawn is dotted with hammocks, lawn games, and adorable Babydoll Southdown sheep, who do double duty as lawnmowers. Sit down for brunch, which on Sundays includes dishes like stuffed French toast, lobster rolls, omelettes, and oysters. Order a bacon Bloody Mary, mimosa, or spiked iced coffee to keep things lively.
Shop and stroll
Make your way to Sylvester Manor Education Farm – it has 226 acres of trails to explore. Check to see if the farmstand is open – as this would mean you could bring back fresh produce and beautiful flowers. Then, head to Shelter Island Heights for some shopping – the island is home to several design shops and galleries. Check out Ram Design Home, which showcases designers and artists including ceramicist Lily Hoffman, photographer Robin Rice, and furniture maker Alfredo Paredes. Also on your list: Heiberg Cummings Design’s The ATELIER for home goods, Pure Soul for apparel and jewellery, and Finley’s Fiction for books and gifts.
Sip your way to sunset
White Oak Farm and Gardens hosts guests in its idyllic back garden every summer weekend. Sip a glass of house wine (the farm partnered with Lenz Winery to make its own rosé) or other local wine and order a cheese and charcuterie board from the King Andrew Cheese cart parked on site – all whilst enjoying live music from local bands.
Next, head to Sunset Beach to stake out a good spot for – you guessed it – sunset. The Sunset Beach hotel is also the place to see and be seen, so be sure to grab a drink at the indoor-outdoor bar. And finally, finish your weekend at Isola, where the Italian-inspired menu features pastas, pizza, and excellent chicken and eggplant parmesan – and make sure to save room for the tiramisu.
