Our Definitive Guide to The Hamptons

By Anna Mack

Ah, “the Hamptons.” Simply uttering those two words conjures up images of everything from cedar-shingled mega mansions and old money charity galas to share houses packed with 30 kids and girls  screaming “yes way, rosé.” The row of villages dotting the South Fork of Long Island could be called our South of France, and if we’re being honest, it can be a tough scene to navigate if you don’t have your bearings. Where you frequent out east, to many, defines who you are and what you stand for. That said, there’s a whole side of the Hamptons that’s much more down to earth. Think: pristine beaches, quaint historic inns, cool seafood joints, old school diners, ice cream trucks, and more. With this in mind, we’ve put together a guide that we think is the perfect mix of high and low, so you can make the most of your summer weekend outside of the city.

Mid-Range Hotels ($150 – $300)
Splurge-worthy Hotels ($300 – $500)

Coffee / Sweets
Drinks with Friends
Dinner for Two
Going Out

Interiors / Antiques / Arts / Gifts
Sites and Sounds


MID-RANGE HOTELS ($150 – $300):

A Butler’s Manor – Southampton
If you’re looking for a cute spot for a getaway with your significant other, check out Butler’s Manor. The bed and breakfast is run by husband and wife team, Chris and Kimberly Allen. It takes it’s name from Chris’s former profession. A proper English butler for over 20 years, Chris has run estates throughout Europe and the United States.

Capri Hotel – Southampton

Photo: Courtesy of the Capri Southampton

Located in Southampton, this boutique hotel offers a Mediterranean aesthetic with a Hamptons color palette. Sit poolside for drinks at Bathe or dine al fresco at Oreya, and we promise this summer getaway will not disappoint.

The American Hotel – Sag Harbor
Located in Sag Harbor, The American Hotel is a quirky historic establishment that feels like it’s straight out of a Wes Anderson movie. Chess boards adorn cocktail tables up front near the bar, so you can play a quick game while you have a cocktail and wait for your table at this must-not-miss restaurant.


Gurney’s – Montauk
With over 145 rooms, Gurney’s is one of the largest hotels in the area and perfect for hosting a wedding. It also boasts a great beach restaurant for drinks or dinner with friends. Our favorite activity? There’s no question: It’s the spa. Go to one of their pop up workout classes and then head there for a relaxing massage or facial.

The Chequit – Shelter Island

Photo: Courtesy of The Chequit

This is where island time and historic Long Island vibes meet. The boutique inn offers quaint rooms for a relaxing getaway or the summer house, which can accommodate you and all of your friends.

The Maidstone Hotel – East Hampton
This place is the epitome of picturesque East Coast Americana. Hydrangeas line the entrance of the inn and bicycles are parked out front for guests looking to go for a ride. With 19 individually designed rooms and cottages, the inn could serve as the perfect home base during a wedding weekend.

Topping Rose House – Bridgehampton

Photo: Courtesy of The Topping Rose House

Topping Rose House is an inn and a restaurant, but also a place to see and be seen. Located in Bridgehampton, the Victorian home has been transformed into a modern luxury refuge. Enjoy quite stand alone cottages, suites, spa services, and the delicious farm-to-table dining.

Our break down of what to pack in your Hamptons beach bag 



Hampton Coffee Company – Watermill

Photo: Courtesy of The Hamptons Coffee Company

Nothing says Summer like ice coffee! Hamptons Coffee, as it’s called for short, not only has the best iced coffee on the island, but they also make a mean lobster roll at lunch.

Sip ’n Soda – Southampton & Bridgehampton

Photo: Courtesy of Sip ‘n Soda

One of our favorite spots in Southampton—the Sip ’n Soda is the best place to take the kiddos or your parents for lunch. The old school soda shop will give you all of the jukebox feels. Add rainbow sprinkles to your shake for the full experience or give their summer peach flavor a try (pictured above). And, if you’re in need of a caffeine boost, we suggest going with a vanilla Coke.

Tate’s Bakeshop – Southampton

Photo: Courtesy of Tate’s Bakeshop

The famous cookie brands’ flagship store is located in Southampton and can be a one-stop shop for all of your hostess’ gift needs.

The Golden Pear – East Village & Bridgehampton
Start at the Golden Pear for a light breakfast snack before hitting the shops on Main Street in Southampton. Navigating the crowd in such a tiny space can be a bit of a cluster, but the smoothies and sandwiches are well worth the stress.


Jue Lan Club – Southampton

Photo: Courtesy of Jue Lan Club

The name translates to “determination to create change,” and the small bar started in New York City as a respite for artists and those devoted to the avant-garde in the 1930s. Now, with their second location, that cool downtown vibe has made its way to Southampton. Enjoy good music, artisanal cocktails, and locally sourced, gourmet snacks.

Southampton Social Club – Southampton
The Southampton Social Club is the perfect day-to-night party location—drink rosé outside in their luxurious cabanas and then make your way inside for drinks and sushi from the eclectic dinner menu.

Sunset Beach – Shelter Island

Photo: Courtesy of Sunset Beach

Sunset Beach offers breathtaking views. Their outdoor tables and yellow striped cabanas are the perfect setting for watching the sun go down with a glass of rosé in hand.

Wolffer Estate’s Wine Stand – Sagaponack

Photo: Courtesy of Wolffer Estate

Walking the vineyards of the Wolffer Estate during the 6:00 P.M. golden-hour should be on every Hamptons-goers’ bucket list. There’s live music during cocktail hour and cheese plates galore—honestly, what’s not to love? Don’t forget to hit up the rosé drive through!


Calissa – Watermill

Photo: Courtesy of Calissa

Nestled in Watermill, Calissa offers the freshest Greek cuisine on the island. Make a reservation as this hot spot fills up quickly!

Crow’s Nest – Montauk
Located on Lake Montauk, Crow’s Nest is a popular spot to take in the sunset. Couples and friends gather at their bar down on the water while they sip on their rose and wait for their dinner reservation. Post sunset, the fire pits with twinkle lights above are a perfect place for an after dinner drink.

Sant Ambroeus – Southampton

Photo: Courtesy of Sant Ambroeus

Italy in Southampton is Sant Ambroeus on Main Street. There’s perfectly brewed ice coffee in the morning and gelato in the afternoon, but make sure stop in for lunch or dinner and try the burrata appetizer—three words: to. die. for. Hands down, this is our favorite restaurant in the Hamptons.

The Beacon – Sag Harbor
Sitting on the deck of The Beacon is one of our favorite things to do during the summer. If you go, be sure to try one of their signature martinis—but remember what Dorothy Parker once said: “I like to have a martini. Two at the very most. After three, I’m under the table. After four, I’m under my host.” Proceed with caution.

Pierre’s – Bridgehampton
Located on Bridgehampton’s main drag, Pierre’s is one of our favorite, fun date night or pre-going out dinner spots in the Hamptons. Not only is the food delicious, but they serve rosé from magnum bottles . . . ’nough said.

La Fondita – Amagansett
This roadside stand serves up traditional Mexican food reminiscent of what’s found in street markets and taquerias. Take your chips and guac out back and grab a seat at a one of the many picnic tables for a casual dinner under the stars.

Lulu Kitchen and Bar – Sag Harbor

Photo: Courtesy of Lulu Kitchen and Bar

The chefs cook everything on an open grill, ensuring all flavors are trapped in the cuisine. Make sure to order a wood fire pizza for the table!

Townline BBQ – Sagaponack
For the best BBQ on the South Fork, Townline is the place to go. Serving classic Texas style BBQ and a variety of specialty beers, it’s a great go-to for a casual date night.

The Surf Lodge – Montauk
The Surf Lodge is one of the most popular Montauk bars and restaurants, particularly on the weekends for their summer concerts, but their rooms are what you absolutely must see. Updated last year by Fiona Byrne, they are everything you expect from a Montauk beach hotel.


Grey Lady – Montauk
This place specializes in local seafood and New England fare, but is more well-known for it’s packed dance floor. The line is always impossibly long, but you’re bound to run into people you know.

The Stephen Talkhouse – Amagansett
Back in the day, there was no line, and Jimmy Buffet might show up on a random Saturday night. Now, the line can wrap around the block, and Jay-Z and Coldplay have been known to stop by. The Talkhouse is a Hamptons institution known for its good live music and unpretentiousness.

Ruschmeyer’s – Montauk
Located a mile outside of the center of town, Ruschmeyer’s feels akin to an upscale campground. There are picnic tables, ping-pong, oak trees filled with twinkle lights, teepees, and an outdoor dance floor . . . basically everything you could ever want in a casual night out.



Aerin – Southampton

Photo: Courtesy of Aerin

Aerin Lauder not only owns and runs our favorite boutique shop and lifestyle brand, Aerin, but she also got married in the Hamptons. Earlier this summer, she took the time to reminisce about her Wainscott wedding with OTM. Make sure you stop by her shop on Main Street—there, you’ll find all your summer needs, from the perfect straw hat to a one-of-a-kind hostess gift.

Big Flower – East Hampton

Photo: Courtesy of Big Flower

Located in East Hampton, Big Flower fulfills all your summer linen needs. From towels and beach cover ups to baseball caps, they offer up simple, airy summer essentials.

Club Monaco – Southampton
We know you can order online and in the city, but the Club Monaco stores in the Hamptons just feel chicer. They always seem to stock just the summer dress and flats we’ve been craving.

Figue – East Hampton

Photo: Courtesy of @katrinarazon

Located in East Hampton, Figue offers luxe-bohemian clothing and accessories. If bold prints and textiles are your thing, this shop is well worth a visit.

Malia Mills – Southampton
The absolute best bathing suits of all time. The swimsuit collection at Mailia Mills in Southampton is our go-to for classic, chic swimwear with a flattering fit.

Roberta Roller Rabbit – Southampton & East Hampton

Photo: Courtesy of @carolinemcurran

Pajama-rama—need we say more! Roberta Roller Rabbit has our favorite printed PJs for summer. We also can’t get enough of her beach cover-ups and home accessories.


Gustavo Oliveri Antiques – East Hampton
Gustavo antiques offer a collection of art deco pieces with a Hamptons flare. Find something you can’t live without but won’t fit in your carryon? Don’t worry—they ship!

Hildreth’s Home Goods – Southampton

Photo: Courtesy of Hildreth’s Home Goods

There is no place like Hildreth’s—established in 1842, the store is the largest source for interior and exterior home goods in the Hamptons. Linens, soaps, gifts, and cashmere—Hildreth’s has everything.

English Antiques – Southampton
As the store name suggests, English antiques specializes in country pieces that are perfect that work well in a second home or your shabby chic apartment in the city.

Mecox – Southampton
Situated on an expansive three acre property, Mecox has home goods for both the interior and exterior. Here you will find an extensive collection of furnishings, coffee table books, and objet d’art as well as garden scenes with outdoor sculpture and boxwoods. For over 25 years, Mecox has been a one-stop-shop for designers and homeowners alike.

Homenature – Southampton

Photo: Courtesy of Homenature

This store specializes in mid-century, modern pieces, and the white and neutral color palette really evokes the beach.


Bay Street Theatre – Sag Harbor

Photo: Courtesy of the Bay Street Theatre

The Hamptons is most definitely a beach bums’ paradise, but that doesn’t mean it’s devoid of culture. The Bay Street Theatre offers a variety of musicals, plays, and children’s theatre for the whole family. Many shows debut at the Bay Street Theatre as they work to make their way to Broadway.

Ditch Plain Beach – Montauk
Home to one of the top surfing spots in the Hamptons, Ditch Plains beach is packed from sun up to sun down with surfers and families. Grab lunch at the Ditch Witch food truck and take a walk on the beach while you watch the waves roll in.

Our breakdown of what to pack in your Hamptons beach bag.

Flying Point – Watermill
Located in Watermill, Flying Point is the ideal beach for kids. Go past the main parking lot and unload your gear at the roundabout. There, you’ll find access to an idyllic inlet of gulley water that’s just the right spot for families or those who prefer swimming in warmer temps sans waves. Pro Tip: Keep your ears open for the ice cream truck. Mister Softee often makes a stop.

Guild Hall – East Hampton
Checking out The Guild Hall Center of the Visual Arts—located in East Hampton—is the perfect rainy day activity.

Parrish Art Museum – Watermill

Photo: Courtesy of the Parrish Art Museum

Driving by the Parrish Art Museum in Southampton, you can easily mistake the oblong structure for a barn or farm. Take the time to pull over and explore, and you’ll find a beautiful art museum with an extensive collection of American art and sculpture.