The Hamptons, NY - Jim Flynn's BestWeekends

The Hamptons, NY

The Hamptons, NY 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 South Fork or “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.

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 HamptonSouthhamptonSag HarborWainscottBridgehamptonAmagansettWater 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.


When To Go

This content is only available to active members. Please Login or visit our membership page for details.

Getting There

This content is only available to active members. Please Login or visit our membership page for details.

Getting Around

This content is only available to active members. Please Login or visit our membership page for details.

Things To Do

This content is only available to active members. Please Login or visit our membership page for details.

Dont Miss

This content is only available to active members. Please Login or visit our membership page for details.

Good to Know, Good to Go

This content is only available to active members. Please Login or visit our membership page for details.

Special Things

This content is only available to active members. Please Login or visit our membership page for details.

Where To Stay

1770 House

OVERVIEW 1770 House is a magnificently restored 200 year old white clapboard inn with black shutters, a white picket fence and lush gardens located in the heart of all the activity in East Hampton. An acclaimed restaurant, a cozy pub and luxurious rooms make this a very special weekend retreat. The lobby area is wood...…

View Property Details

American Hotel, Sag Harbor

OVERVIEW Located in a quaint, waterfront village, with just 8 rooms, an excellent restaurant with a spectacular wine list and a bar everyone seems drawn to, the American Hotel is what I would want my hotel to be like if I owned one. This place has personality in an age of minimalist and sterile accommodations....…

View Property Details

Baron’s Cove, Sag Harbor

OVERVIEW Baron’s Cove was built in the 1950’s as the first resort development in Sag Harbor. It quickly became a hub for the creative community and enjoyed visits from a diverse group of celebrities and artists like John and Elaine Steinbeck, Paul Newman, Art Garfunkel, Richard Kind, Jackson Pollock, Willem and Elaine de Kooning, Truman...…

View Property Details
We have a lot more recommended accomodations, but you must be a member to view them! Please login or become a member.

Where To Eat

1770 House

Without a doubt 1770 is one of the most romantic restaurants in the Hamptons. The small elegant and intimate dining room has beamed ceilings and fans and thick crown moldings above walls half painted beige and half covered with a subtle grass cloth. Wall sconces and antiques clocks adorn the walls and the dark hardwood…

View Restaurant Details >

75 Main, Southampton

Scarcely a week goes by, particularly in season, without a mention of 75 Main in Page Six of the New York Post. A celebrity sighting, maybe there was a photo shoot, or perhaps someone got overserved. Whatever the reason, 75 Main is a popular spot with locals and tourists alike. I like it because it…

View Restaurant Details >

American Hotel

The mood at The American Hotel is set with crisp linens, sparkling silver and crystal, soft candlelight and fresh flowers in four elegant rooms decorated in Empire and Victorian antiques and furnishings. What's nice about this place is when you eat alone here, it has the feel of an old men's club, comfortable and cozy.…

View Restaurant Details >
We have a lot more recommended dining locations, but you must be a member to view them! Please login or become a member.

Advance Search

Use our handy tool to search for the perfect weekend with all the features you prefer. Search by accomodation type, recognition, geography, amenity and more. Search now!

May 2020: Little Nell

This months featured property is… charming and sweet. THE ROOMS In 2017, Champalimaud Design refreshed all 86 rooms and suites and all guest floor corridors. The approach was to reinvigorate the spaces to be fresh, light and welcoming, utilizing palettes of blue, tan and grey to complement the relaxed nature of Aspen. Key features include… read more.

Notes From the Road

Hear about our latest discoveries
before anyone else!

CLICK HERE TO SIGN UP!