North Fork & Shelter Island
Mainly, the North Fork is known for its unspoiled farmland and wineries – there are close to 30 vineyards, clustered chiefly around the towns of Jamesport, Cutchogue and Southold – and the Long Island Wine Council provides details of the local wine trail, which runs along Rte 25 north of Peconic Bay.
Long Island's Gold Coast of the roaring 20s, of the Vanderbilts, Chryslers and Guggenheims, not to mention Gatsby, begins outside the suburban town of Port Washington. Castle Gould, the enormous turreted stable at the entrance to Sands Point Preserve and now a visitor center, was once owned by Howard Gould, the heir to a railroad fortune.
Bridgehampton & Sag Harbor
Moving east, Bridgehampton has a more modest-looking drag, but has its fair share of trendy boutiques and fine restaurants. The modest low-slung Enclave Inn, just a few blocks from the heart of the village, is one of the better value accommodation options; there are four other locations elsewhere in the Hamptons.
Don't be fooled by the oh-so-casual-looking summer attire, heavy on pastels and sweaters tied around the neck – the sunglasses alone are probably equal to a month's rent. Some of the highest-profile celebrities have homes here. Catch readings, theater and art exhibits at Guild Hall.
Though the village of Southampton appears blemish-free, as if it has been Botoxed, it gets a face-lift at night when raucous clubgoers let their hair down. Its beaches – only Coopers Beach (per day $40) and Road D (free) offer parking to non-residents May 31 to September 15 – are sweeping and gorgeous, and the Parrish Art Museum is an impressive regional institution.
Montauk & Around
Once a sleepy and humble stepsister to the Hamptons, these days Montauk, at the far eastern end of Long Island, draws a fashionable, younger crowd and even a hipster subset to its beautiful beaches. Longtime residents, fishermen and territorial surfers round out a motley mix that makes the dining and bar scene more democratic compared to other Hamptons villages.