Getaway Guide: Weekend Road Trip To The Hamptons, NY

July 28, 2012 6:00 AM

The Hamptons are the epitome of an upscale getaway, a mere 4.5 hours from Boston. The dining, beaches, nightlife and accommodations cover every base to provide the perfect weekend getaway for any traveler. Mingle with celebrities, socialites and politicians while you spend a weekend in style right here in the Hamptons.

Getting There

Take I-95 south out of Boston and through Rhode Island to exit 84 south toward downtown New London. Merge onto Eugene O’Neill Drive and turn left onto Governor Winthrop Boulevard. Turn left onto Water Street, and then right onto Ferry Street. Take the Cross sound Ferry to Orient. Follow Main Road/New York State Bicycle Route 25 through Greenport, Southold and Cutchogue before turning left at County Road 105/Cross River Drive. Take a left onto Flanders Road/New York State Bicycle Route 24, the follow the ramp to NY-27 east. Continue onto County Road 52/Sandy Hollow Road, which will take you into Southhampton.

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Main Beach
101 Ocean Ave.
East Hampton, NY 11937
(631) 324-0074

Main Beach is one of five beaches in East Hampton that are run by the village. The sand here is perfect for sunbathing or building sand castles, while the clean water keep you here playing in the waves all week. This beach is family friendly, as it is lifeguard protected, and there are clean bath houses available for use. If you get hungry after a long day, stop by the snack bar and grab a hot dog or ice cream. Parking is permit only, so walk down Ocean Avenue instead.

What To Do

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Sail Montauk
435 E. Lake Drive
Montauk, NY 11954
(631) 522-5183

Click here for pricing

Sail the waters of Montauk on a Catalina 22. Relax on a private sail, or learn more in an intro to sailing class. Tailor your sailing package to include swim time, an experience of what it’s like to be on the crew, a sunset sail or even book multiple boats. The professional captains will keep you safe and informed while you are on the water. Bring a bottle of wine to make this the perfect romantic addition to your vacation.

Related: Road Trip: Bristol, Rhode Island

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SL East
44 Three Mile Harbor Road
East Hampton, NY 11937
(212) 627-1235

This nightlife spot offers more than 7,000 square feet of indoor and outdoor space. With its modern, chic styling this is the perfect place to grab a drink and dance, or catch a live performance. Its high-quality service and upscale clientele make for an enjoyable evening out. SL East brings the nightlife of Manhattan to the Hamptons for the summer with its special events and appearances by leading artists and renowned DJs.


edgewater Getaway Guide: Weekend Road Trip To The Hamptons, NY

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Edgewater Restaurant
295 E. Montauk Highway
Hampton Bays, NY 11946
(631) 723-2323

Edgewater offers a mixed menu of Italian and seafood dishes, along with an extensive wine list. Arrive early to try the two for one early bird menu. Indoors, you will find candlelit tables, cathedral ceilings and windows with breathtaking views. Outdoors, the deck overlooks Shinnecock Bay. The delicious food, attentive service and vantage point of this restaurant make it a must when visiting the Hamptons.


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The Huntting Inn
94 Main Street
East Hampton, NY 11937
(631) 324-0410

Click here for reservations

The Huntting Inn is a historic bed and breakfast located on Main Street in East Hampton, which was named one of the most beautiful Main Streets in America by National Geographic. The comfort and serenity of this inn will allow for total relaxation during your stay. Rooms range from small queen to king suite, and include wireless Internet, beach passes, continental breakfast, beach chairs and beach towels. Dine in style without leaving the premises at Palm Restaurant, which is a favorite of many celebrities, politicians and socialites during the summer months.

Related: Guide to Boston Walking Tours
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Kim Vareika is the owner of Vareika Personal Training and Yoga in Plainville. She has been in the fitness industry for over ten years, and believes that wellness is about more than just physical health. When she is not teaching, practicing, or writing, she resides in Bridgewater where she enjoys spending time with family, friends, and her nephew Caesar. Her work can be found at