GREENPORT
Lure: Low-key and eminently strollable, this former whaling town has all the requisite historic charms: clapboarded antique shops, quirky local boutiques, old-timey signage and Instagram-ready waterfront restos dripping with authentic nautical décor.
Crowd: Brooklyn meets the North Fork. Hipsters and artists dig the village’s unpretentious vibe and its much-heralded farm-to-table food scene (literally, with farms right down the road on Route 25).
You might run into chef Tom Colicchio (a resident of nearby Mattituck) at gourmet market Salamander’s on Front, and, in a nod to Greenport’s cool factor, “Girls” has filmed here.
Brix & Rye.Caroline Rochetta Photography
Must do: Order a flight of small-batch suds at Greenport Harbor Brewery from either of its two locations: a converted firehouse in the village or a newly expanded brewpub and restaurant in nearby Peconic. With 28 wineries, including Bedell Cellars and Jamesport Vineyards, in a 15-mile radius of Greenport, a wine-tasting trip is a must; craft your own itinerary via the Long Island Wine Council or go for a guided excursion with North Fork Wine Tours.
Eats: On any given sunny Sunday, locals will be dockside at Claudio’s Clam Bar for standout chowder and even better mudslides.
Foodies flock to the seasonal menu at the buzzy Frisky Oyster, while the subterranean speakeasy Brix & Rye wouldn’t look out of place in Brooklyn.
Stay: The year-old American Beech is known for its hopping outdoor bar scene, but in a private carriage house above the restaurant are five large guest rooms, outfitted with modern white and gray accents, Restoration Hardware beds, original art and C.O. Bigelow products (from $250/night).
For sale: 5-bedroom, 4-bath, 1920s Bantam Farm in nearby Nassau Point features 259 feet of private beach on exclusive Horseshoe Cove, $3.7M. Agent: Sheila Izzo, North Fork Real Estate, 631-384-5551.
For rent: Memorial Day-Labor Day, $55K, 3-bedroom, 3-bath bayfront home has wraparound deck, private beach and boat parking.
Walking distance to village. Agent: Kate Nickles, Douglas Elliman, 631-566-1690.
BELLPORT
Location: On Long Island’s Great South Bay, midway between Manhattan and the Hamptons; 1-hour drive from NYC, or the LIRR has a Bellport stop.
Lure: This small, beautifully preserved bayfront village is replete with 19th-century Colonial-style homes, local merchants — including an old-timey barbershop and Carla Marla’s Ice Cream Parlor — and a sprinkling of restaurants. Another draw is its proximity to an actual ocean beach: Residents can hop the 8-minute ferry to the private Ho-Hum Beach, part of the Fire Island National Seashore.
Crowd: Though many famous folks call Bellport home — Isabella Rossellini and Charlie Rose among them — the town also appeals to hippies and hipsters, artists and organic farmers, theater fiends and science geeks and craftspeople of all kinds. They all share a love for Bellport’s natural beauty and a dedication to preserving its waters, woods and wildlife.
Must do: Tennis and golf at the Bellport Country Club, or for a more back-to-nature experience, canoe or kayak the Carmans River. Get your dose of culture with a Broadway show at the Gateway Performing Arts Center or check out an art-house flick at the Plaza Cinema & Media Arts Center in nearby Patchogue.
Eats: Locals swear by the steaks at Porters on the Lane in Bellport Village; no-frills Spicy’s Barbecue (631-286-2755) serves up tasty ribs and excellent collard greens. And you don’t have to play golf to enjoy a casual breakfast or lunch at Peter’s on the Green at the Bellport Country Club.
Stay: Most weekenders rent a house, as the closest upscale accommodations are in Eastport, about a 20-minute drive east. There you’ll find the Seatuck Cove House, a bed-and-breakfast set on the bay, with water views from every room (from $175).
For sale: In the heart of the village, a 3-bedroom, 3-bath classic shingled cottage built in 1940 with renovated chef’s kitchen and large back deck, $1.65M. Agent: Arthur Garry King, Swan Realty, 631-848-6412.
For rent: June, $10K, July $24K; 4-bedroom, 3-bath country-style home with heated pool, pool house and outdoor shower. Agent: Anthony Gandolfo, Rice Realty Group, 917-975-5646.
SHELTER ISLAND
Location: Nestled in the Long Island Sound; 10 minutes by ferry from Greenport on the North Fork or from Sag Harbor on the South Fork, or charter a StndAIR seaplane: the “Sunset Hooky” package flies you from NYC to Sunset Beach in under an hour and includes a three-course lunch ($735, starting June 17).
Lure: The pace slows the moment you step into this peaceful enclave, whose forested hills, secluded coves and quiet beaches offer respite from the frenetic Hamptons scene. And that’s not likely to change anytime soon — more than a third of the island is set aside as a nature preserve, so development (and visitor numbers) are largely kept in check.
Crowd: Old-school, Vineyard Vines-wearing types dominate, but Andre Balazs’ Sunset Beach hotel, which introduced a Euro-style, late-night DJ-party scene to the otherwise sleepy isle in the late ’90s, keeps trendy folks in the mix. Notable summer residents include design duo Jonathan Adler and Simon Doonan; Louis C.K. recently bought a waterfront Tudor.
Must do: Pick your perfect beach: Crescent Beach, with its proximity to Sunset Beach’s buzzy restaurant, is all about the people-watching (and amazing sunset views). The calm, shallow waters at Wades Beach make it popular with families; out-of-the-way Shell Beach, on West Neck Harbor, teems with wildlife. Explore it all with a paddle-board tour or rental from Venture Out.
Eats: Locals head to Sweet Tomato’s in Shelter Island Heights for affordable homemade pasta and wood-fired pizza (631-749-4114), while Vine Street Café’s market is picnic-perfect with fresh, to-go gourmet sandwiches and salads. Now that hotspot Red Maple (at the Chequit hotel) has lunch and Sunday-brunch service — featuring lots of locally sourced veggies — your midday hunger pangs will be no more.
Stay: The 37-room Chequit opened last year and it’s already garnered a spot on Condé Nast Traveler’s 2016 Hot List. Its modern spin on Victorian décor includes a spiffy new lobby and porch area that transforms into a guest-only wine-and-Champagne lounge come evening (from $195).
For sale: 6-bedroom, 5-plus-bath Ram Island estate set on 5.4 acres features pool and pool/guest house, $10.75M. Agents: Donald Bindler, M. Wein Realty, 631-749-0999 and Peter M. Turino, Brown Harris Stevens, 631-903-6115.
For rent: MD-LD: $110,000, 3-bedroom, 4-bath renovated contemporary beach house set on a secluded acre close to ferry. Agent: Rima Mardoyan, Brown Harris Stevens, 631-537-4342.