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

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 a model, 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.

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 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

The Hamptons are also accessible by private planes (East Hampton Airport), boats and helicopter service ( Blade flies from NYC to East Hampton. Seats average @ $795 one way.

Getting Around

You could very easily select a town and enjoy what the area has to offer on bicycle or by using local transportation. Uber and Lyft are available in the Hamptons.

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.

Things To Do


The Hamptons beaches are renowned for their pristine beauty. Long wide stretches of white sand. One travel magazine rated them among the best in the world. What is somewhat unusual is that there are ocean and bay beaches. The bay beaches being less crowed with calmer surf.

Main Beach in East Hampton is the preferred beach by most, it is where all the beautiful people flock. Many, however, like Georgica Beach, Apaquogue Road and Lily Pond Lane. Equally as beautiful, less crowded with a backdrop of mansions and estates. In season, parking is an issue without a town permit. Best to take bicycles. My favorite beaches are in Montauk, unspoiled, uncrowded and no attitude.


Montauk Downs State Park. 15 minute drive from East Hampton. Called, “Shinnecock Hills for the poor unwashed” Some think it is the best public course in America. As close to Scottish golf as you can get. Greens fees an unbelievably low $36.

An 1 1/2 hours away in Farmingdale is the mecca of public golf, Bethpage, sight of the 2002 U.S. Open. Great golf is never too far!


There are public courts at East Hampton High School (2 Long Lane), Bridgehampton High School (Montauk Highway), Southhampton High School (Leland Lane) and Mashashimuet in Sag Harbor (Main Street). Fees range from $10-$20/hour. The East Hampton Indoor Tennis Club offers both indoor and outdoor facilities to non-members.


You can bike just about anywhere. Montauk Highway has a wide shoulder which makes it easy to get from town to town. Bike routes are marked. My favorite walking/running area is the East Hampton Village Trail, a beautiful wooded trail along a brook, accessed from David’s or Hunting Lane. Best place to rent bikes is Sag Harbor Cycle Co, Main Street in Sag Harbor.

Boat Rental

Puff & Putt, Main Street, Montauk, rents canoes, rowboats, kayaks and small sailboats for use on Fort Pond.Main Beach Surf & Sport, Montauk Highway, Wainscott is located across from Georgica Pond and has just about anything you may need for water related sports. Uihlein’s in Montauk does the same.

Boat Ride

East End Kayak Tours at Main Beach Surf & Sport (above) offers group kayak tours of Georgica Pond and Harbor Tours, on the 45 foot wooden American Beauty, Long Wharf in Sag Harbor offers 90 minutes sightseeing tours of Sag Harbor and Peconic Bay narrated by a nature and history guide ($35) or a 2 hour sunset cruise ($25)


Montauk is considered the Sportfishing Capital of the World because many of the world record fish were caught off Monatuk. Three choices for fisherman; surf fishing (for striped bass) which can be done just about anywhere, but Montauk beaches are considered the best, charter boats (up to six people) or party boats (up to 100 people).

ProSport Charters (631-668-2154) can arrange a charter for you or call the Blue Fin IV Most of the party boats are out of Montauk. Viking Fishing Fleet is the largest.

Horseback Riding

Deep Hollow Ranch, Montauk Highway, Montauk. Oldest working cattle ranch in the country. There are 1 1/2 hour trial rides for $40, but the better choice is the 2 hour beach ride for $50. Pretty special.


“Long Island has the potential to be the East Coast version of the Napa Valley, a food and wine mecca” says Marvin Shanken, Publisher, Wine Spectator. Long Island is home to over 50 vineyards ranging in size from 2 acres to 600 acres. The wines are winning awards nationally and internationally and are served in some of the finest restaurants in New York City.

Here’s some favorites and considered to have the best wines;  Channing DaughtersPaumanok,  Macari, Shinn Estate VineyardsLenz Winery, and Bedell. Look for events like the Long Island WinterFest.


Art galleries are big time in the Hamptons and if you are there during the season, there seems to be art show openings every night. There are galleries scattered in many towns, but the largest concentration is in East Hampton. Ann Kolb on Main Street features American crafts and folk art, Wallace Gallery on Main Street specializes in 19th and 20th century American art and Wally Findlay Galleries, Main Street displays old masters, impressionists and contemporary artists. See also White Room Gallery in Bridgehampton and Fitzgerald Gallery in Westhampton Beach.


The Hamptons offer a treasure trove of interesting and exquisite antique shops. Many are only open during the summer. We’ve listed a few of the more interesting which are open year round. Call for hours.
English Country Antiques. Bridgehampton and Southampton. As the name suggests, specializes in English antiques and reproductions.
Urban Archeology. Bridgehampton. Great idea. Salvages architectural pieces from buildings about to be demolished.
Fisher’s Antiques. Sag Harbor. Country pine antiques and reproductions. Painted and distressed furniture.
Black Swan Antiques. Sag Harbor. varied product availability.


Parrish Art Museum. Southhampton.  Focuses on work by artists from the artist colony of the South Shore and North Shore. South Fork Natural History Museum and Nature Center.

Theater/Performing Arts

Westhamption Performing Arts Center. World-class performing arts, music, dance, comedy and cinema from around the world. Guild Hall, East Hampton. Arts, entertainment, and education center for the community


Plenty to keep the shopaholic busy. Many designers, Betsey Johnson, Cynthia Rowley, Eileen Fisher to name a few, have shops in East Hampton in the summer. There’s Tiffany’s and Polo and Coach in East Hampton, a Villeroy and Boch Factory Outlet in Southhampton and many shops and boutiques in the other towns. East Hampton, Southhampton and Sag Harbor have the most choices.

Dont Miss

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

The Best Of...

Food & Drink


All of our Featured Properties offer breakfast and the American Hotel in Sag Harbor is also open to the public. Babette’s on Newtown Lane in East Hampton has lots of healthy stuff, but it’s good…Don’t miss getting a donut at Dreesen’s, also on Newtown Lane. The Golden Pear in East Hampton has lots of fans and Citarella’s has breakfast take-out. Our new favorite is Brent’s General Store in Amagansett for breakfast sandwiches, bakery goods and fresh OJ. Feeling like a bagel and a “schmear”. Head to Goldberg’s in Montauk, East Hampton and Amagansett.


75 Main in Southampton is an Italian/New American restaurant serving breakfast, lunch/brunch and dinner. In nice weather, this celebrity favorite spills out onto the sidewalk and after dark its lounge is one of the Hamptons “hot” spots. Our Friday afternoon brunch was delicious with their roast beef tenderloin hash with potatoes, sweet potatoes, onions, sweet peppers and poached eggs.

Rowdy Hall, down a little alley off Main Street in East Hampton offers delicious pub food and traditional “fish & chips” and with its roaring fireplace, is perfect for a rainy or cold day. In nice weather tables are set out on the patio. The Palm Steakhouse in East Hampton is open for lunch on weekdays in a cozy space with comfy booths in the Hunting Inn. Also in East Hampton, Cittanuova offers a delicious lunch menu and outdoor seating. Any meal at the American Hotel is good. Lunch or Sunday brunch at the Ram’s Head Inn on Shelter Island is a wonderful experience in late Spring thru early Fall. Sitting on the terrace overlooking the water is a wonderful way to spend part of your afternoon.  On the North Fork, a lunch at the exquisite Jedidiah Hawkins Inn in Jamesport is an adventure and oh so romantic. Great food and wine list.

Any Meal

Pierre’s in Bridgehampton may be the Hamptons best all-around restaurant serving every meal in a warm and cozy setting. Tables on the sidewalk in nice weather, a delightful book lined back room with a fireplace and booths in the main room. The food is excellent, the service is charming and they have a Wine Spectator award winning list. Try the burger on a brioche bun.


How many small towns have a branch of two nationally famous steakhouses? You’ll find the venerable Palm Restaurant right on Main Street in East Hampton with all its wonderful charm; leather booths, fireplaces and hardwood paneling. Bobby Van’s in Bridgehampton is the other. Both fantastic.


Unfortunately, not my thing, but locals rave about Sen in Sag Harbor on Main Street. Very cool decor. Zagat says, “Satisfied sushi samurai give their seal of approval to this Sag Harbor Japanese for its fresh, creative rolls and sexy, stylish atmosphere; yes, the service may be lacking (but the waitresses are beautiful) and it could be renamed sin, because at these prices you’d think they were flying the fish in from Tokyo, but it’s a true sen and be sen Hamptons hot spot, and there’s a reason people wait in line to eat here; N.B. no reservations taken.”


I’ve always been a fan of the burger at Rowdy’s, but the opening of Union Burger Bar in Southampton has created a whole new standard. Incredible selection of burgers, the best fries in the Hamptons and they have a cocktail bar! Yeah!

Oyster Bar

Morty’s Oyster Stand, on the site formerly known as Cyril’s Fish House, features an assortment of daily rotating fresh oysters, Maine uni and other raw bar noshes. Boswick’s on the Harbor in East Hampton is another seasonal oyster and raw bar. The Bell & Anchor in Sag Harbor and its sister restaurant Fresno in East Hamption offer $1 Montauk Pearls every Sunday night.


Duyrea’s in Montauk is a casual waterside, seasonal restaurant, but if you are there Spring-Fall and want the freshest seafood (particularly lobster), this is the place. Literally right off the boat fresh!

Wine Bar

The #1 place to drink wine in the Hamptons is the American Hotel in Sag Harbor. First, because it is open all the time, second because its a great venue, but most importantly, it is the only Wine Spectator Grand Award winner in the Hamptons. Honorable mention to 1770 House, a Wine Spectator Award of Excellence winner and Pierre’s Bridgehampton, Best of Award of Excellence winner, both open for lunch.


The #1 place for cocktails and an incredible sunset is the Montauket Hotel. Few places anywhere can match it. For year round enjoyment, try the Living Room at the Maidstone. Blazing fireplaces in winter, great drinks and don’t miss some of their Swedish meatballs as an app. The Blue Parrot,  seasonal, sits down a small alley off Main Street in East Hampton. Amazing margarita’s, guacamole and chips. Sen, in Sag Harbor has a great vibe and a good Saki and Wine menu. The American Hotel is a gathering place for locals, Pierre’s in Bridgehampton has a lively Happy Hour crowd and Topping Rose, also in Bridgehampton makes some of the most creative cocktails around. When the weather is nice, I love the Firepit at Gurney’s on Montauk.

Wine Shop

On the North Fork, you can purchase wine at any of the 50+ wineries. In the Hamptons on the south shore, locals rave about Towne Cellars in Manorville for selection of quality wines.

Picnic Fixins

Citarella’s, Main Street, East Hampton. Just about anything you can think of from sandwiches to salads to prepared foods. This is one of those fun places for foodie’s. It’s enjoyable just strolling the aisles and looking at all they have to offer. Great place to pick up dinner if you are staying in and cooking.

Get Cheesy

Three great choices for wonderful selections of cheeses and pates; Cavaniola’s Gourmet, Amagansett, Citerella’s, Main Street, East Hampton and the Village Cheese Shop in Mattituck on the North Fork.


Morning Paper

Hampton Bagel on North Main opens at 6am, papers are usually there by 6:30. Good coffee and bagels too!

While Away a Rainy Day

When its cold, locals congregate at Rowdy Hall around a warming fireplace. A bit of Irish flavor. Pierre’s is open all day with great food and wine and in Sag Harbor, the American Hotel and Page at 63 Main are a great gathering places.


Maidstone Park Beach on Three Mile Harbor. See Special Things.

After Dinner Fun

Assuming you, like me, want to steer clear of the clubs and all the craziness, The Maidstone  in East Hampton and the American Hotel in Sag Harbor, offer weekend entertainment, usually in the form of a piano player. Both are wonderful, cozy places, great just for an after dinner drink, made even better with the piano bars.

The Firepit at Gurney’s Montauk is a wonderful after dinner drink spot with music, a great vibe and those magical ocean views.

Get Pampered

Naturopathica, just outside East Hampton on Montauk Highway in the Red Horse Plaza. Full day spa services. Recommended by the locals.


East Hampton Gym, behind Citarella’s on Main Street in East Hampton. Branches in Sag Harbor and Southamptom. No frills, full range of equipment. $20/day.

Special Things

Special Things

This BestWeekends Exclusive uncovers special things to see, do and experience that you won’t find in any guide book. Often they are only known to locals or people who have visited many times. These are things that will truly make your weekend special, things that will make you say, remember when we long after the trip is over.

Clambake for Two

Stop at Towne Cellars, get a nice crisp Chablis and then head over to Claws on Wheels, (19 Race Lane, East Hampton) and create you own Clambake for Two with clams, lobster, mussels, corn and new potatoes. ($24.95 each). Add some sides of corn bread and chowder and you’re good to go down to Two Mile Hollow Beach in East Hampton. Great way to end the day.

Sampling the Grape

Long Island continues to gain respect from the wine world for the wines it is producing. There are over 50 vineyards now on the East End of the island. A day traveling from vineyard to vineyard, learning about winemaking and sampling the fruits of their labor is a day well spent. Long Island WineToursand North Fork Wine Tours are two reputable companies that will help create a great day for you.

Where To Stay

1770 House

OVERVIEW of 1770 House

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. View Property Details

American Hotel, Sag Harbor

OVERVIEW of the American Hotel

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…

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Baker House 1650, East Hampton

OVERVIEW of Baker House 1650

Baker House 1650 is the most magnificent B&B we have encountered in all our travels. Designed in 1910 from a 1648 farmhouse, this architectural marvel is a stunning property and unlike anything you have experienced before. Beautifully decorated in period antiques…

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Baron’s Cove, Sag Harbor

OVERVIEW of Baron's Cove

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…

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Gurney’s Inn, Montauk

OVERVIEW for Gurney's Inn Montauk

Gurney's Inn Montauk has undergone a multi-million dollar renovation led by new owners George Filopoulos and Lloyd Goldman that has transformed the once stodgy old resort into the new hot spot at the East End. Wunderkind designer Michael Kramer has created 38 new oceanfront suites with grand terraces overlooking…

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Gurney’s Star Island Resort & Marina, Montauk

OVERVIEW of Gurney's Star Island

Gurney's Star Island has been around for quite some time, (80+ years to be exact) and its distinctive lighthouse is familiar to many. An extensive 2009 renovation refreshed the property and it is now an even better destination, ideal for couples or families. The Yacht Club is the setting…

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Sound View, Greenport, NY

OVERVIEW of Sound View

We came upon, Sound View, a wonderful little gem of a hotel on the Eastern end of Long Island, via a mention in a magazine and it looked so interesting that we immediately booked an overnight. Built @1935 as a "motel", it…

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The Harborfront Inn, Greenport

OVERVIEW of the Harborfront Inn

The historic village of Greenport, New York is the perfect base for a visit to the North Fork of Long Island. Ideally located at the eastern end of the North Fork, Greenport gives you easy access to many of the best wineries…

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Topping Rose, Bridgehampton

OVERVIEW of Topping Rose

In 2005, two old friends, Bill Campbell and Simon Critchell, joined together to purchase and restore Topping Rose House, which was built in 1842 for Judge Abraham Topping Rose and his family, and transform it into a year-round luxury boutique hotel.  The stunning design by architect Roger…

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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…

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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…

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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.…

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East Hampton Grill

We were big fans of Della Famina and were sorry to see it go, but the East Hampton Grill, opened in 2011, is a wonderful addition to the dining scene in the Hamptons. Part of the Hillstone Restaurant Group, the restaurant joins the Rutherford Grill in Napa and the Palm Beach Grill in Florida among…

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Nick & Toni’s

I like anything roasted or grilled over a wood fire and Nick & Toni's has taken that kind of cooking to a new level. Despite its reputation as a celebrity favorite, there is no pretension here, this restaurant is really about the food. The décor is crisp and clean, white walls and tablecloths, oak and…

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North Fork Table & Inn

The summer of 2006 may well become known as the beginning of the food revolution on the North Fork. That's when the North Fork Table opened and if it is the precursor of what is to come, the area will be a food mecca in no time. How can you go wrong, with a restaurant…

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Like Balthazar in NYC, Pierre's in Bridgehampton is my favorite all-round restaurant in the Hamptons. You can eat any meal here, or just stop in for wine and cheese. The food and atmosphere are wonderful. Pierre's is like having St. Tropez, St. Barts and the Hamptons all in one restaurant, A mahogany bar festooned with…

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