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The Hamptons, NY
Weekend Vacation Getaway

Destination Overview

At the far eastern end of  Long Island the Expressway (Rt.495) ends and the road splits, winding around Great Peconic Bay, going north and south. To the North is called the North Fork, to the south The Hamptons. Like many siblings the areas couldn't be more different. Th Hamptons is the wild child; glitzy and unpredictable. The North Fork is the quieter of the two, more grounded, more stable.

The North Fork is rural with many more year round residents and a wine industry that continues to gain recognition for its fine wines. It is not as crowded, even in season, as the Hamptons, yet offers plenty of wonderful places to stay and eat and just as many activities. While the ideal time to visit the Hamptons is late Spring and early Fall, the North Fork is great any time of year. The wine community has succeeded in making the area enjoyable even in the dead of winter.

If we are to believe the New York newspapers, the Hamptons are filled with self-indulgent models, celebrities and wannabees on a trek to see and be seen. I guess for about 8 weeks in July and August, that’s probably true. In that time frame, people pay outrageous amounts of money to rent mansions along the south shore of Long Island, the roads between the towns are always clogged, beaches are jammed and the top priority seems to be how to get into the “hot” club each night.

Click picture to enlargeEast Hampton Point Inn BarRowdy HallO'Malleys

But the Hamptons that insiders know and love, is the Hamptons that exists the other 10 months of the year. The series of small, bucolic villages that dot the southern shore of Long Island, NY and known as the “Hamptons” starts at Westhampton and stretches out to the eastern tip of the island at Montauk. It includes the towns of East Hampton, Southhampton, Sag Harbor, Wainscott, Bridgehampton, Amagansett, Water Mill and others.

The Hamptons have long been the summer respite of New Yorkers seeking to escape the heat of the City. Twentysomethings who “share” houses during the season, rub shoulders with celebrities, politicians and high powered business types during a frantic summer of partying that leave most exhausted by Labor Day.

But before the crowd gets there and after they have returned to the City, the Hamptons offer a wonderful weekend retreat of pristine beaches, quaint shops, antique stores, wineries, top rated restaurants and plenty of things to do to occupy your time.

There is a Hamptons personality to fit just about any mood. Tony East Hampton offers upscale shops like Tiffany and Ralph Lauren, Sag Harbor is a charming waterfront village, Montauk is a laid back and casual beach town and the North Fork evokes thoughts of the California wine country.

See my Photo Scrapbook.

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Click picture to enlargeJL EastLong Island WineryBlue Parrot

Making Your Travel Plans

To make your travel plans you can go to our Weekend Planner for all the contact information.

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Getting There

You pretty much have to go through New York City to get to the Hamptons, whether you are driving, flying or taking other transportation. It is about 100 miles from NYC to East Hampton which is in the middle of the Hamptons. Driving takes about 2 hours and 15 minutes but can take much longer during the season. Hampton Jitney offers the best bus schedule from Manhattan and costs about $47 round trip. Schedules are available at www.hamptonsjitney.com. Trip takes about 2 hours. Long Island Railroad has an extensive schedule to the Hamptons and costs about $36 round-trip. Travel time is about 3 hours. Schedules are available at www.mta.nyc.ny.us/lirr/.

The Hamptons are also accessible by private planes (East Hampton Airport), boats and helicopter service (www.flynortheast.com).

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When To Go

The Hamptons are most enjoyable May through mid-June and September thru mid-October. The weather is great, everything is open and the crowds are manageable. July and August are when New Yorkers empty out the City and traipse to the Hamptons. It is also when all the celebrities and politicians are there. If your goal is to make Page Six in the Post or to hook up with Paris, July and August are your best shot.

The less crowded North Fork is enjoyable any time of year, even the summer when the crowds are more manageable than on the south shore.

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Getting Around

You could very easily select a town and enjoy what the area has to offer on bicycle or by using local transportation.

If however, you would like to do a little exploring, perhaps to visit some wineries, to play golf out at Montauk or to sample the restaurants in other towns, you will need a car.

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There’s no longer any need to roll the dice on where you stay or to settle and stay at a “safe” national chain. BestWeekends Travel Advance Team takes the worry out of where to stay when you go away.

The BestWeekends Travel Advance Team does all the work for you. We research each destination by scouring the guidebooks, articles, blogs, reviews and rating systems. Then we visit the destination and stay in the properties. Finally, we talk to the locals to be sure we didn’t miss anything. The result: we post on our site only the best of what we experienced. You can book with confidence knowing that “we’ve been there” and that no one pays us for a review. Inside see our Featured Properties.


When you are away on vacation, there’s few things worse than a bad dining experience. We agree, so we follow the same process for identifying restaurants as we do for accommodations, but with an extra step. We believe that the best dining experience has the strongest combination of food, ambiance and service. Good food is a given in our recommendations, but the best food in the world just doesn’t taste as good in a poor setting and the best setting with poor service just doesn’t cut it for us. The BestWeekends Travel Advance Team only presents those restaurants that meet our strict criteria. Mangia….enjoy! See our Favorite Restaurants.

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Things To Do

Much to do in the Hamptons; shopping in quaint boutiques, tours of excellent wineries, gallery browsing, antique hunting, laying on the beach and walking in the woods. For the more active there is world class golf, tennis, perhaps the best big game fishing in the East, boat rides, canoeing, biking, and horseback riding on the beach. Here's the complete list of Things To Do.

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BestWeekend' s Exclusives

After selecting our favorite places to stay and eat, we sat down and made a list of all the other things that would save you time and make your stay more enjoyable. The result is “Special Things” and “Good To Know, Good To Go,” BestWeekends Exclusives.

Special Things identifies unique, fun and romantic things for couples to do together in a particular destination. Good to Know is our list of the “best” of everything from breakfast to burgers, cocktails to after dinner fun and much, much more. Why stumble around trying to find the “best”….we’ve already done it for you!

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Don't Miss

  • East Hampton Village Trail
  • Winery Tour
  • Drinks at East Hampton Point
  • Dinner at the American Hotel
  • Montauk Lighthouse

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News and Resources

The East Hampton Star, The Independent and Dan's Hamptons are the newspapers that will keep you up to date on local info. Hampton's Magazine is the local lifestyle publication and Hamptons.com is the on-line guide to everything in the Hamptons.

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