The Hamptons may seem like a world where only the poshest of New Yorkers and international A-listers spend their summers. While the Hamptons do indeed welcome the rich and famous from May to September, there is another — less ritzy and luxe — side of this residential enclave. Take, for instance, the area's natural beauty: the sunsets over the undulating reed-covered marshy fields, or those misty fall mornings that are always accompanied by the seasonal honking of the Canadian geese, and that strong, briny smell of the Atlantic. And then there's the gorgeous natural light — one of the many reasons why artists and writers flocked to the East End of Long Island during the second half of the 20th century.
In three days, begin to discover all that Long Island has to offer. Its beautiful beaches stretch along the Atlantic coast, affording the perfect place to relax and take in the surroundings. Dive into its delicious local seafood, whether at the tables of roadside clam shacks or gourmet restaurants. Get to know its small towns and the locals who spend their winter months there; admire its historic homes and streets.
For accommodations we recommend the warm, historic Bassett House in East Hampton, which has been around since 1830; the family-friendly Ocean Vista Resort in Amagansett; or the Southampton Inn, a romantic, Tudor-style inn.
THE HAMPTONS DAY 1: Southampton, Shopping, Parrish Art Museum
After spending the night at the Southampton Inn, home to the Southampton Pool and Tennis Club, head into town to grab a bite to eat and to explore. Southampton is one of the few Hamptons that remains fairly lively even through the winter months, when smaller towns board up the doors to their retail shops and even their restaurants. In downtown Southampton, pull up a chair at the Sip 'N Soda Luncheonette for some old-fashioned diner food and people-watching.
Then take a stroll through the historic areas around Jobs Lane, an easy walk from the center of town. Here, you'll find Gilded Age mansions and early settlements such as the Rogers Mansion and the Pelletreau Shop.
Southampton is also a shopping mecca. Homenature caters to the stylish contemporary interior, and Hildreth's — the oldest department store in the United States — sells the softest towels, fluffiest duvets and plenty of accessories for the nursery. Calypso sells a mix of elegant and funky bathing suits in bright colors. At Hatchlings, you can purchase two-ply cashmere sweaters and Parisian shirts and dresses for children, as well as the most adorable baby outfits. A 20-minute walk north takes you to Tate's Bake Shop, where you can stock up on the chocolate chip cookies that Food Network star Rachael Ray deemed as the best in the country. The cakes and the chocolates are worth the trip, too.
For lunch, consider Silver's — a family-run, seafood-centric restaurant. In the winter, the homemade soups are a great choice; in summertime, the sandwiches are a delight.
In the afternoon, take a walk through the Parrish Art Museum. Artists have been drawn to the region ever since 1870, when the Long Island Railroad extended its service to Southampton. The museum takes this history into account, and the permanent collection is home to more than 2,500 works in a variety of styles. Several famous names are featured, including James Whistler and Dan Flavin.
For dinner, classic red sauce joint La Parmigiana is a crowd pleaser. The restaurant also houses a prepared foods store selling goods such as homemade gnocchi.