How to Spend the Summer in the Hamptons

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By Pam Teel

Spending the summer in the Hamptons can be pricey but thanks to sites like airbnb, visitors to this enchanting region of villages and towns along the East End of Long Island can make their stay as low-key or as extravagant as they like. The rise of short-term rental sites like Airbnb have made week-long and even weekend stays in the Hamptons increasingly accessible so you can chose whether to live economically or lavishly for the duration. You can choose from many five star restaurants or dine on lobster rolls by the side of the road.

July through Labor Day is the true high season. That’s when the social scene hits its peak, with food festivals, charity benefits, community fairs and special events. September and October are lovely times to visit, too. The weather is usually still nice and there’s still a lot of things to do and you won’t have to deal with the crowds.

From the city, the simplest way to get to the Hamptons is to drive. It’s a two-to-three-hour trip from Midtown Manhattan to East Hampton Village, depending on traffic, and shorter or longer if your destination is Southampton or Montauk, respectively. Be prepared for summer traffic.

Many locals also travel to the Hamptons by bus, via the ever-popular Hampton Jitney, the nicer Hampton Luxury Liner, or a similar line, all of which make stops in central areas of the main hamlets and villages. Another good option is the Long Island Rail Road. Local trains can take three hours to reach Montauk from Penn Station, but there’s also an express train to the Hamptons on summer Friday afternoons departing around 4:06. Imagine how quickly that fills up. Plan on getting there early for a seat. Adventurers with cash to spare can hop on a seaplane or a helicopter from Manhattan. Luxury helicopter rides can cost up to $800.00 one way so opt for a more private less thrills helicopter service. You can always call for an uber to meet you when you embark.

The Viking Fleet of cross-sound ferries travels between Montauk and New London, CT., Block Island, and Martha’s Vineyard (a summer add-on only). Also, Amer- ican, Southwest and Frontier airlines fly into MacArthur Airport in Islip, which lies about an hour west.

The best way to summer in the Hamptons is to rent a house, cottage, or condo for one month, two months, or the entire summer — that is, Memorial Day through Labor Day. Out East is a great place to start searching, with thousands of summer rentals available. While inventory on the East End is substantial, many experienced summer visitors start locking up places as early as February.

August through Labor Day is the most expensive time to book. It’s rare to find even a small cottage for less than $7,000 a month and prices for the most luxurious homes run well into six figures. If you don’t have that kind of dough to drop, check out airbnb for a good deal on a place.

For a more affordable visit, consider the North Fork of Long Island, which is wonderfully scenic. While it doesn’t have the sweeping Atlantic beaches of the Hamp- tons, the North Fork’s rural setting, top-quality wineries, and calm bay beaches make it extremely attractive, and historic towns like Greenport offer plenty of restau- rants and activities to keep visitors occupied.

The Hamptons is limited in terms of hotel options. Montauk remains the best place to find rooms, with options at a variety of price points. Sag Harbor features the American Hotel, a 180-year-old Main Street fixture with a 30,000-bottle wine cellar, and Baron’s Cove, a waterfront hotel with a lively bar and restaurant, is just a short walk from town. Shelter Island has Sunset Beach, a Euro-style bayside hotel and outdoor bar and restaurant founded by Andres Balasz. Bridgehampton boasts the Topping Rose House, where the rooms run over $1,000 a night in the high season. There’s a Jean-Georges restaurant and cozy bar on-site.

You could also pitch a tent at Montauk’s Hither Hills State Park for just $35 a day (reserve early), or East Hampton’s Cedar Point State Park. Summer in the Hamptons is all about sun, sand, and surf. The Hamptons has miles of world-class ocean beaches that offer amenities like snack bars and food trucks or all the solitude you like. Many of the best are totally public, too — you don’t need a club membership or permit. Mecox Beach in Bridgehampton – Unless you have a local permit, many of the best beaches have hefty daily rates (think $50 to $90) for parking, as well as small lots that fill up quickly. Walk, bike or take a car share to the beach to save money.

Southampton and East Hampton’s respective villages have the biggest collection of boutiques and pop-up shops, but Sag Harbor and Bridgehampton have some unique stores, too, and just as many terrific restaurants. Amagansett’s claims to fame include the Stephen Talkhouse, a no-frills live music venue that features notable acts. The spas at Baker House and Naturopathica in East Hampton, and Gurney’s in Montauk, are great places to unwind. The once-sleepy fishing village of Montauk continues to enjoy a reputation as a hipster destination. It has the best surfing waves and hot night spots like the Surf Lodge, Duryea’s Lobster Deck, Navy Beach, and the Crow’s Nest.

Kids love the putt-putt course in town, and hitting John’s Drive-In for a burger and delicious homemade ice cream. Just a few miles way sits Montauk Lighthouse, which was commissioned by George Washington in 1792. The on-site café sometimes hosts live music in high season.

Drive by the hedge-rowed mansions along Further Lane and Ocean Road, or visit the many farm stands bursting with local produce, baked goods, and prepared food.

If it’s a more activity you’re looking for, you can book a private surfing lesson, or rent bikes, kayaks, paddleboards, motorboats and sailboats at numerous Hampton’s locations. At the marinas on the either side of Lake Montauk you can also board a deep-sea fishing trip, book a whale-watching cruise, or rent a jet ski.

Windsurfers and kite surfers like to take their gear to Napeague Bay. Water skiers often head for Sag Harbor Cove or nearby Long Beach. There are public golf courses in Sag Harbor and at Montauk Downs, as well as a par 3 track at Poxabogue Golf Center in Bridgehampton, where there’s also an on-site driving range.

Kids especially enjoy the South Fork Natural History Museum and Nature Center in Bridgehampton, and the Long Island Aquarium in Riverhead, which houses sharks, seals and other water-loving critters. Don’t leave the Hamptons without stopping at one of its many farm stands where you can find fresh fruits, vegetables, and home baked goods.

The Parrish Art Museum in Water Mill has the area’s best collection of art and exhibits. Guild Hall in East Hampton is a close second and offers a terrific lineup of entertainment. So does the Bay Street Theater in Sag Harbor. The Southampton Arts Center has a robust calendar of events, and the Pollock-Krasner House offers limited tours of the home studios where the great husband-and-wife artists Jackson Pollock and Lee Krasner worked. (Above info from

Don’t forget to take advantage of the Hamptons in September and October when things are still hopping and the crowds have thinned out! For more info check out: