Montauk
surf · fishing · casual · outdoorsyThe end. Surf town with a hangover.
Laid back, salty, surf-and-fish. Once a fishing village, then a Brooklyn-hipster outpost, now somewhere in between. Flannel and flip-flops are formal wear. The lighthouse, the cliffs at Camp Hero, and Ditch Plains define it.
Good for: Surfers, anglers, hikers, people who think East Hampton tries too hard.
Skip if: You want fine dining and boutique shopping without driving 20 minutes.
East Hampton
polished · boutique · manicured · quiet luxuryPolished. Hedge-trimmed. Old money meets new.
The most manicured of the villages. Main Street is all whitewashed shingle, Ralph Lauren, and Tiffany pop-ups. Quietly the wealthiest zip code on the East End, but the village center is genuinely walkable and pretty.
Good for: Shopping, gallery hopping, beach clubs, people-watching.
Skip if: You hate dress codes and reservation culture.
Southampton
traditional · WASP · old money · tennis whitesTraditional. WASPy. The original.
The oldest English settlement in New York State and it shows. Gin-and-tonic country, hedge-row estates, Meadow Club tennis, Southampton Hospital benefit. Less trendy than East Hampton, more traditional.
Good for: Coopers Beach, Parrish Art Museum, classic Hamptons.
Skip if: You want to feel young and edgy.
Sag Harbor
artsy · walkable · literary · indieArtsy, walkable, the writers' village.
An old whaling port that became the Hamptons' bohemian alternative. Walkable Main Street, the windmill on Long Wharf, the American Hotel. Writers and editors live here. Faces north onto the bay so the light is different.
Good for: Walking after dinner, the bookstore, the cinema, harborside drinks.
Skip if: You came for ocean swims (the bay beaches are calm but not surfy).
Amagansett
quiet · tiny · farm-to-table · beachyQuiet. Two blocks of Main Street. Don't blink.
Wedged between East Hampton and Montauk. The smallest of the major hamlets and proud of it. Stephen Talkhouse for live music, Indian Wells Beach for actual swimming, the farmstand at Amagansett Square.
Good for: Couples who want to disappear, Indian Wells Beach.
Skip if: You need nightlife or shopping.
Bridgehampton
farmland · polo · central · open skyFarmland and polo.
The agricultural belt. Open potato fields, Bridgehampton Commons (the only real strip mall in the Hamptons), the polo grounds at Two Trees, the Topping Rose House. Geographically central, which makes it a useful base.
Good for: Anyone driving to multiple villages; horse people; polo Saturdays.
Skip if: You wanted a walkable village center.
Water Mill
residential · quiet · artThe windmill, the duck pond, the discrete estates.
Tiny hamlet between Southampton and Bridgehampton, organized around a working windmill and the Parrish Art Museum nearby. Mostly residential, very wealthy, very quiet.
Good for: Parrish Art Museum, a discreet base.
Skip if: You want any street life at all.
Wainscott
estate · ruralBlink-and-miss-it between Bridgehampton and East Hampton.
Mostly farmland and estates. Georgica Pond is here. Famous for its absence of a town center.
Good for: People renting a house and not leaving it.
Skip if: You want anything walkable.