The Hamptons, NY

An 85-plus-year Montauk fixture on Fort Pond Bay, transformed from a no-frills lobster deck into the East End's most photographed waterfront table. Lobster rolls, Peconic oysters, and big shareable salads at sunset prices.

A 45-year roadside shack on the Napeague stretch between Amagansett and Montauk, all umbrella-shaded picnic tables and plastic ware. Fried clam strips, chowder, and both a cold and a butter-poached hot lobster roll.

The Napeague seafood shack known by the LUNCH sign on its roof, running since 1965. Mayo-heavy chopped lobster roll, chowders, steamers, and homemade pies, with a full bar and a kids' menu.

An informal East Hampton seafood house on Pantigo Road, market-umbrella patio and seaside decor. Lobster bisque, hot and cold lobster rolls, fried platters, and soft-serve to finish.

East Hampton's 1988 special-occasion default, wood-oven Mediterranean-Italian with a long-running celebrity reputation. Wood-roasted whole fish, house pastas, and a seasonal vegetable focus.

A casual takeout seafood shack right on the dock at Sag Harbor's Long Wharf, water and boat views from picnic seating. The creamy whole-claw lobster roll is the standout on a crisp bun.

A James Beard-recognized East Hampton bakery on Newtown Lane turning out naturally leavened breads, viennoiserie, house gelato, and a short savory menu. The Hamptons' serious bread program.

A small Sag Harbor Turnpike cottage doing American food with Southwestern leanings, year-round breakfast and lunch plus weekend dinners. Breakfast burritos, tortilla soup, and rotating specials from the garden.

The Milanese cafe-restaurant on Southampton's Main Street, espresso bar and gelato counter up front, Northern Italian dining behind. A see-and-be-seen lunch and a proper afternoon coffee stop.

A counter-service Mexican spot on the Amagansett highway since 1998, bright and casual, built for after-beach eating. Tacos, tortas, and aguas frescas from the team behind Nick & Toni's.

A Southern Italian mainstay with a Sag Harbor location and a private garden, fresh pasta and a reliable see-the-scene crowd. A go-to for a real meal before a night out in the village.

Run by six local fishermen on eight waterfront acres at Montauk's inlet, with catch coming off their own boats. Fluke piccata, tuna tartare, and fresh sushi with working-harbor views.

A South Indian counter on East Hampton's Newtown Lane built around large made-to-order dosas and uttapams, traditional and inventive fillings, house chutneys. A genuinely different option in a seafood-and-Italian town.

A Sag Harbor Japanese mainstay since 1994 on Main Street, sushi bar plus an expanded hot kitchen, with a back garden. Widely held as the best sushi on the East End.

An easygoing Water Mill sushi room on Montauk Highway between Southampton and Bridgehampton, reasonable for the area. Known for the spicy tuna sandwich and a no-frills, locals-eat-here feel.

A hidden-alcove beachfront restaurant off Montauk's backroads, with one of the best setups on the East End, tables nearly on the sand. Seafood-leaning American with sunset over the bay.

An English-French gastropub relocated to Amagansett's Main Street, dark wood and a long bar. Bavarian pretzels, the burger, buffalo wings, and homemade ice cream, from the Nick & Toni's group.

A regional Mexican kitchen next to La Fondita in Amagansett, a proper sit-down counterpart to its fast-casual neighbor. Ceviche, rotisserie meats, and a deep tequila list, open year-round.

A historic East Hampton tavern and inn dining room on Main Street, candlelit and old-Hamptons. Meatloaf with garlic gravy and seasonal seafood upstairs, a more casual tavern menu in the cellar.

A full-service Wainscott fish market since 1972 with a takeout kitchen, made-to-order fried platters and a generous lobster roll. The old-school market-counter alternative to the sit-down shacks.

A Bridgehampton bistro since 2001 on Ocean Road, market-driven and ever-changing under chef Jason Weiner. Moules frites, plats du jour, and a long bar that locals treat as a default.

An East Hampton bagel counter on Pantigo Place, chewy bagels and stacked breakfast sandwiches at prices that undercut everything around. The morning-line spot before the beach.

A Sag Harbor village tavern doing a tight American menu, anchored by a much-talked-about dry-aged burger with American cheese. A solid dinner-and-a-drink room without the resort theatrics.

A Montauk roadside drive-in since 1967, small-batch homemade ice cream made daily plus open-grill burgers. The classic after-beach cone stop, unchanged for decades.

A 2,300-acre Nature Conservancy preserve covering a third of Shelter Island, reached by a short ferry from the South Fork. Color-coded loops from a 1.5-mile walk to an 11-mile circuit through oak woods, salt marsh, and bay shore.

An easy 2.8-mile loop in Hither Hills off Napeague Harbor, winding through migrating sand dunes, a phantom forest, and cranberry bog. The dunes literally move with the wind here.

A 607-acre East Hampton park on a peninsula into Gardiners Bay, with a roughly 3-mile shoreline loop to the 1860s Cedar Island Lighthouse. Sandy paths, low seagrass, and water views in most directions.

A quiet network of one-to-three-mile loops in Montauk County Park around a tidal pond, bridle paths, and woods. Light foot traffic and birding, a contrast to the crowded ocean beaches.

Montauk's premier surf beach, a two-mile stretch of sand cliffs and dunes with the East End's most consistent, forgiving break. Walkable shoreline, a surf-and-watch culture, and food trucks in season.

A 105-acre red-maple swamp at the head of Sagg Pond near Sagaponack, with a one-mile boardwalk-and-trail loop. Shaded, quiet, and a complete change from the dunes and beaches.

The rugged park wrapping Montauk Point Lighthouse, with bluff and beach trails along the Atlantic at Long Island's tip. Seal-watching off the rocks in winter and big open-ocean views.

Sagaponack's wide, low-key ocean beach off Sagg Main Street, dune-backed and quieter than the East Hampton and Southampton flagships. A long walkable shoreline with a small lifeguarded stretch.

East Hampton's cultural anchor on Main Street, combining an art museum with the John Drew Theater for plays, music, talks, and the SummerDocs film series. Local and internationally known artists in one building.

A rebuilt nonprofit arthouse on Sag Harbor's Main Street, three small screens, a rooftop bar, and a lobby cafe. First-run independents, special screenings with visiting filmmakers, and Sunday kids' matinees.

A 30-plus-year Sagaponack winery on Sagg Road known for its dry rose, with a reservation-only tasting room and a seasonal roadside wine stand. Vineyard rows, sunset pours, and a polished hospitality setup.

A Bridgehampton winery on 28 acres making an unusually wide range of varietals and skin-contact wines, with a sculpture garden of owner Walter Channing's work. A low-key, experimental counterpoint to the bigger estates.

A professional nonprofit theater on Sag Harbor's Long Wharf, opposite the windmill, with mainstage productions, comedy nights, and benefits. The East End's serious live-theater venue.

A hands-on Bridgehampton museum on the Sag Harbor Turnpike, one of Long Island's most-visited, built for young kids. Climb structures, dress-up stations, a wind-power windmill, and magnet fishing.

A roughly 30-acre Amagansett nonprofit farm on Main Street with a market, kitchen, and cafe, plus a large CSA. Pick-your-own days, farm classes, and a genuine working-farm feel rather than a stand.

A Montauk waterfront restaurant, bar, and music venue on Fort Pond, known for sunset crowds and a summer concert lineup. Coastal food and a scene that defines a certain Montauk energy.

New York's oldest lighthouse, commissioned under George Washington in 1796, standing at the easternmost tip of Long Island. Climb the 137 iron steps for an Atlantic-and-Block-Island view, then walk the rocky shoreline below.

Herzog and de Meuron designed a single long barn-form building in Water Mill for the East End's art legacy. Permanent rooms hold Jackson Pollock, Willem de Kooning, and Roy Lichtenstein alongside rotating regional shows.

The Springs home and studio where Jackson Pollock poured Autumn Rhythm and Blue Poles, and where Lee Krasner painted until 1984. The barn floor is still paint-splattered; the house holds their library and records as Krasner left it.

Jack Lenor Larsen's 16-acre East Hampton sculpture garden, where designed landscapes wrap large works by Dale Chihuly, Yoko Ono, and Buckminster Fuller. Paths move through dune grass, allees, and ponds.

An 1845 Greek Revival mansion built for a whaling magnate, now holding scrimshaw, harpoons, and documents signed by Washington and Jefferson. The whale-jawbone entrance arch is the village's signature photo.

Artist Robert Dash's two-acre Sagaponack garden, made over decades from 1967, with painted blue-and-yellow structures and rooms that shift around every corner. A working artist's garden, not a manicured estate.

A 1680 saltbox farmstead on the East Hampton village green, one of the best-preserved English colonial farm complexes in the Northeast. Period rooms, barn, and yard beside the Home, Sweet Home Museum.

Southampton's wide ocean beach, repeatedly ranked among the best in the U.S. and named the country's top beach in 2025. Powder sand, grassy dunes, lifeguards, and chair-and-umbrella rentals.

East Hampton's flagship ocean beach at the foot of Ocean Avenue, white sand with a classic 1930s pavilion, lifeguards, showers, and a small snack concession. The village beach locals default to.