So you’re heading to the Hamptons for a week. Seven in heaven as we like to say out this way (full disclosure: no one out here says that). But seven days is definitely enough time to get a good taste of what the Hamptons have to offer.
If you need advice about restaurants checkout our dining guide and if you’re still looking for a place to stay, head over to our accommodations guide. If you’ve already got all of that figured out, read on and get ready for a great week.
Day 1: Montauk
We’re going to flip the script and start at The End—as Montauk is fondly known. Why is it known as The End? Because that’s where it is.The Montauk Lighthouse sits at the easternmost end of Long Island (fun fact: it was commissioned by George Washington) and the surrounding park is a great place to spend a morning exploring. There’s Money Pond where Captain Kidd is rumored to have buried some of his treasure and the old radar dish and the surrounding bunkers from the Montauk Project, which has inspired as many conspiracy theories as JFK’s assassination. Extra bonus: beach hikes where you can spot seals sunning them selves on the rocks and sand surrounding the lighthouse.
As you head back to town, consider stopping at Deep Hollow Ranch, America’s oldest cattle ranch, where you can saddle up and go for a ride. Or, if playing the cowboy isn’t appealing, hang a right and head up to Montauk Harbor. There, you’ll find one of the East Coast’s largest fishing fleets as well as a number of dock side restaurants serving up some of the freshest seafood you can find—it’s literally straight off the boat.
Back in town, a few spots of note are John’s Pancake House, which has serious breakfast and a pretty good burger, too, and Shagwong, which is a popular watering hole and a great place to have dinner. And if you’re around after dark, you’re going to want to stop into the Memory Motel. You may recall hearing of the Memory Motel in the Rolling Stones song of the same name. Don’t be fooled—although they spent time in Montauk at Andy Warhol’s estate, the first time they walked into the Memory Motel they were quickly kicked right back out by the owners. It didn’t stop them from drinking and carousing around town—and they did plenty of that at the aforementioned Shagwong.
Party on.
Day 2: Amagansett and The Springs
Amagansett is the furthest town east that is still considered the Hamptons proper (Montauk is its own strange land, though still populated by plenty of folks who could aptly be described as Hamptonites). But in Amagansett and The Springs you’ll find bucolic laid back areas that have some of the East Ends most spectacular beaches and quiet back roads.The Springs has long been a popular refuge for artists and it’s also the last remaining bastion of the Bonackers, which is the name given to the group of families who have lived in the Hamptons for generations and have worked the fields and waters around the area to make their living. (To get a glimpse into the lives of the baymen and the East End’s fishing history you should checkout the East Hampton Marine Museum in Amagansett.) The Springs is where Jackson Pollock came to work after leaving New York City and where he developed his drip painting technique that turn the art world on its head. You can visit his studio and the house he shared with artist and wife Lee Krasner, which has been preserved just as it was while he worked there. Just down the street from the Pollock-Krasner House is The Springs General Store where Pollock would occasionally pay for groceries with his paintings (not a bad deal by today’s prices) and where you can get great sandwiches. If the weather is good you can also rent kayaks there and go for a paddle in Accaobonac Harbor where the baymen still clam.
Back in Amagansett head down to the beach and have a wander along the shore before heading back into town—pause to try and peak over the 12-foot fence around Gwyneth Paltrow’s house, which she recently purchased—and stop in town for dinner at Meeting House, which is fine dining and family friendly. After that, you’re going to want to head over to the Stephen Talkhouse, which is one of the area’s few venues to catch live music. It’s a casual—sometimes cramped—place that attracts locals and visitors alike, but you will definitely hear some good music, whether it’s a nationally known act or one of the local bands, like the Nancy Atlas Project.
Dance.
Day 3: East Hampton
A few years back a National Geographic poll named East Hampton Village as America’s Most Beautiful Village. It was a well-deserved win as you’ll be hard pressed to find a more picturesque little hamlet anywhere. From the Town Pond at the western of town where swan’s glide gracefully over the water’s surface to the eastern end of town and the old windmill that sits on the village green, in East Hamtpon it’s hard to take a bad picture.Wandering up and down Main Street and Newtown Lane is a bit like a stroll down Fifth Avenue with chic boutiques and art galleries lining the streets and little shops offering high-end luxury goods. If shopping is of interest, then East Hampton is the place to do it.
Once you’re shoped out some other points of interest in East Hampton include Guild Hall, which is one of the oldest cultural institutions in the Hamptons, and—bear with us on this one—The East Hampton Library. It may not seem like a logical stop, but the Long Island Collection is worth a quick perusal after getting your retail fix.
When hunger hits, East Hampton is the place to be with its surfeit of fine dining options. One of the Hamptons’ most famous restaurants—and the one most often frequented by the famous—is Nick & Toni’s on North Main Street. Pair fantastic food, an amazing wine list and the not-out-of-the-realm possibility of getting a table next Steven Spielberg or Renee Zellweger and you have the formula for a winning meal. Another great option is The 1770 House, where you can go the white tablecloth route upstairs or head downstairs to the pub—and take “pub” with a grain of salt because it’s not a beer-on-tap, greasy-burger-joint kind of place—and settle in in front of the fireplace for a fantastic meal. Steak lovers will want to checkout The Palm—the East End outpost of the renowned steak houses—and if the kid are in tow, Rowdy Hall, with its wood-lined walls and an atmosphere to match its name, is the place to go.
Day 4: Bridgehampton, Wainscott and Sagaponack
Halfway between Southampton and East Hampton are the towns of Bridgehampton, Wainscott and Sagaponack. One of the most popular areas for second homeowners because of its location and beauty, this is also the best spot to do a little wine tasting and get a glimpse of the Hamptons from the days before subdivisions supplanted potato fields.No day in this area starts without breakfast at The Candy Kitchen. It’s THE breakfast spot. Actor Roy Scheider is there most mornings and you can grab the local papers, have a seat at one of the booths and tuck into a traditional breakfast.
After breakfast, if you’re up for some activity, there are two great options. Georgica Pond sits at the easternmost end of Wainscott and stretches from Route 27 down to the ocean—and it’s lined by the homes of billionaires. Spielberg’s place is there, as are Martha Stewart and Ron Perelman and hedge funders galore. If you want to get a glimpse into the backyards of the big boys the best way to do it is by renting a kayak from Main Beach Surf + Sport. You can get a glimpse of some palatial properties, enjoy the beauty of the pond and paddle down to the beach and go for a walk. If you’d rather pedal than paddle, Cycle Path Bikes in Wainscott offers bike rentals and you can take a long and meandering ride down to Main Street in Wainscott, glimpse the ocean out over the farm fields and have a stop by the Foster Farm in Sagaponack and grab lunch at the Sagg Main Store.
An afternoon of wine tasting is in order. Two of the South Fork’s three wineries are in the area, Wolffer Estates Vineyards and Channing Daughters Winery. Both have beautiful tasting rooms, awarding winning wines and great deals on cases so that you have something to sip after you’ve left the Hamptons.
When you start thinking dinner, start thinking about Almond or Alison. Both are well-loved and have big followings and they differ mainly in menu offerings, rather than atmosphere and price. Almond is bistro fare in an intimate setting while Alison’s menu is drawn form the local produce that’s available and changes with the seasons. Either way, you’re going to eat well.
Day 5: Sag Harbor
In the 1800s, Sag Harbor was one of the most important whaling ports on the East Coast and its population was greater than that of New York City. Ships from around the world were anchored in the harbor and the wealthy whaling captains built mansions along Main Street and the little side streets, which today are undergoing a renaissance as they are restored to their original glory by their new owners. And while The Springs may have attracted artists, Sag Harbor seems to have attracted writers. Herman Melville stayed at The American Hotel and wrote there and John Steinbeck made it his life-long home.While national brands have taken up residence on Main Street in East Hampton and Southampton, Sag Harbor has eschewed this kind of retail development and tried to stay true to its past. Main Street is lined by big brick buildings and little shops ranging from the 5 and 10 to Romany Kramoris Gallery, and not a Gucci between.
The Sag Harbor Whaling Museum sits at the south end of Main Street, bordered on both sides by the whaling captains’ houses and it’s a great place to take the kids. Wandering the back streets between Main Street and Route 114 is a must, as that’s where you’ll find the beautiful old homes that were built during the whaling boom and, after languishing in decline for decades, are now being restored by new owners eager to return them to their former glory. Take a walk out on the Long Wharf and get a look at the yachts that anchor in the harbor and stop in for a drink at The Corner Bar, where the burgers can’t be beat.
Sag Harbor tends to have one of the largest year-round populations and the restaurants offer a range of options. The American Hotel is high-end, fine dining at its best. Sen offers exceptional sushi, Dockside has great seafood and Paradise Café offers exceptional New American fare. And at night, the only dive bar between the Shinnecock Canal and Montauk, Murf’s Backstreet Tavern, is the place to belly up to the bar.
Day 6: Southampton and Water Mill
Southampton was the first area that was popularized by wealthy, summering New Yorkers at the turn of the century. (Mainly because it was where the train tracks from New York City ended.) The Estate Section, which is bordered by the Atlantic to the south and Hampton Road on the north, is where the grand mansions were built on sprawling estates—all of which are hidden well behind the hedges that are de rigueur in the Estate Section. But you’re in luck, because the best time to explore the area is in the fall and winter when the leaves are off the trees and you can see beyond the privet into these magnificent estates. Drive the area or rent a bike from Rotations and go for a pedal.Main Street and Jobs Lane are lined with stores—think blue blood, Upper East Side style—and you should definitely make a stop at The Parrish Art Museum, where they have an amazing collection of turn of the century art.
When it’s time for lunch there’s only one spot to go: Silver’s. They’re not even open for dinner, so you know that your lunch is all they’re thinking about. For dinner the best spots to head to are 75 Main if you’re in the mood for fancy food and Barrister’s if a burger and beer is a better fit for the agenda.
Day 7: West of the Canal
The Shinnecock Canal divides Southampton for Hampton Bays, Westhampton and Quogue—it’s sort of the unofficial border between the two distinct areas in the Hamptons and there’s plenty to see over on the other side.An afternoon in Quogue is a must and after a spending a day in East Hampton, you might not even realize you’re on the same island, never mind in the same state. Quiet, reserved and the weekend home of editor and author Tina Brown and her husband Harry Brown as well as CNN anchor Anderson Cooper, Quogue is often called the anti-Hampton. The Inn at Quogue reflects this and is the perfect spot for lunch or dinner.
One must while you’re in Westhampton is a drive down Dune Road, which is a narrow strip of sand with the Atlantic on one side and Moriches Bay on the other. After a nice scenic drive head back to town where the streets of Westhampton Beach are lined by eclectic shops and bordered at the western end by the Westhampton Beach Performing Arts Center where they have first rate musical acts on a regular basis as well as performances and shows.
And that’s the end of your week in the Hamptons.
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