A Comprehensive Guide To The Hamptons – From West to East

To Stay

Accommodations in this area of Long Island can be tricky, but if you can get a reservation at Topping Rose House, Canoe Place Resort or The Baker House 1650 you’ll be in for a luxurious stay. To skip the sticker shock of a luxury B&B, the most cost effective way to stay is to search Airbnb, where you can rent rooms, full houses and even sign up for luxury “glamping.”

Take the LIRR from the city, the Hampton Jitney from the Upper East Side, drive out in a rental car or, if budget isn’t a problem, fly out on a private Blade helicopter.

Westhampton

With so much area to cover, it is easiest to experience the Hamptons from West to East. The perfect journey starts in Westhampton—the first enclave you’ll pass on your way down Route 27. For lunch, Flora serves thoughtfully sourced seasonal dishes in a chic, upbeat environment. Pair any dish with one of their craft cocktails—like their namesake, gin-based Floradora. If you are looking for a whimsical treat stop by Shock, a local ice cream shop that is famous for their cotton candy topped cones and shakes. For cocktails, Daphne’s serves artfully concocted refreshments with ingredients like lemongrass-ginger syrup and exotic fruit nectars. An established haven among locals, John Scott’s Surf Shack is a fun outdoor seafood spot with a water view. You can grab a lobster roll, fish tacos or cool off with a frozen drink. John Scott’s also turns into a bar at night if you're looking to hang with the true Hamptonites.

Hampton Bays

A lesser known village, Hampton Bays hides its fair share of gems in bayside restaurants and quiet beaches. Start your day by picking up a fresh focaccia and mozzarella sandwich at Scotto’s Pork Store and take your bounty to Tiana or Ponquogue Beach for a day in the sun. For a picturesque dinner, Rumba is a classic taco spot situated on the Shinnecock Bay. Popularized for their modern take on classic tacos and duck empanadas, they also offer an award-winning Key Lime pie. If you pay the tropical venue a visit, make sure to try the Caribbean Rum Punch, which you can get pitcher style—believe me you’ll want more. After dinner, board the ferry, lovingly called “the Rhumboat,” and get a lift to Cowfish, a new American restaurant with great cocktails and an outdoor area that ’s perfect for lounging, playing games and listening to live music on the weekends. 

Southampton

My stomping grounds, Southampton (yes, it's one word, something you’ll want to remember if you plan to fit the role of a local), is touted by many as the true start to the Hamptons. During your stay, start your morning by skipping the overpriced brunches and heading to Sip'n Soda instead. This place hasn’t changed a bit since it opened in 1958. Run by a local family, they serve classic diner-style food like egg sandwiches, pancakes and their famous Cherry Lime Rickey—a drink recipe passed down for generations.

There is plenty to shop for in Southampton. If you have kids, you’ll want to take a walk down Jobs Lane where you’ll find Bean 2 Tween and Stevenson’s—conveniently located down the street from each other. Bean 2 Tween is a kiddo’s wonderland, bursting at the seams with clothes and toys for the coolest kids in town. Stevenson’s, a family owned toy store, might overwhelm you upon first glance but the kids will be in heaven. 

You can’t visit the Hamptons without buying merch—how else will people know you were there? Locals will say the best merch is found at Flying Point Surf Shop but Breezin’ Up is a classic choice. Although not local, MadHappy has brought its comfy loungewear to Southampton for the summer. The seasonal shop is located off Jobs Lane in what was originally an old school auto garage, and is packed with Hamptons branded apparel in bright summer colors. For vintage shopping, try Le Closet for an assortment of modern designer consignment. If you’re looking to score items that could have been in Carrie Bradshaw’s closet, Collette’s Basement on Main Street won’t disappoint. There, you’ll find racks on racks of vintage designer that may or may not have come directly from the closets of celebrities and Hamptons elite. 

In my opinion, some of the best beaches are in Southampton. You can pick up day passes at Flying Point Beach, or try your luck at some of the cozier spots down Meadow Lane, like Road G. If you’re looking for more fun in the sun, Flying Point Surf School has been hosting private lessons and summer-long camps for kids for over 20 years. Slather your nose in zinc before meeting up with an instructor to hang ten. There is a major golf community in the Hamptons, but most clubs like Shinnecock Hills Golf Club, home of the 118th US Open Golf Tournament, are restricted to members only. 

Try to schmooze a guest pass out of a local, or head across the street to Southampton Golf Range to practice your strokes. There, you’ll also find a mini golf course and Local Burger Co., said to be one of the best burgers in Southampton. A hidden gem in the Village, the Southampton Arts Center (SAC) displays a rotation of contemporary artists’ work in the summer. The best part?—it’s free! Currently, they’re showing a graffiti exhibit that’s on view until July 20. SAC also hosts frequent outdoor events featuring musical performances and feature films. Check out their website for a full calendar of events.

Watermill 

Watermill can seem like more of a passthrough location as you head further East, but here you’ll find great restaurants and farm stands run by families that have lived in the area for decades. On your way through, stop by Hampton Coffee Company for a freshly roasted latte or matcha. This location has a full-service cafe serving traditional brunch as well as authentic Mexican dishes. Suki Zuki is a can’t miss sushi spot with fresh fish brought in daily. Try their famous chopped chicken teriyaki salad to start. The area is also packed with farm stands like the Green Thumb and Corwith’s Farm Stand–don’t miss fresh apple cider donuts at Milk Pail when the season is right.

The Parrish Art Museum is a hidden gem for art lovers. There, you can find exhibitions that include works by Andy Warhol, Fairfield Porter and Roy Lichtenstein—all of whom have ties to the East End. If you are a fan of pop art, keep an eye out for the upcoming exhibit, Kaws: Time off, which will be displayed on July 14. If a spa day is in order, Shou Sugi Ban House is a luxurious retreat and architectural marvel inspired by Japanese principles of wabi-sabi and a spirit of openness and exploration. You can book a full-day spa treatment or even an overnight visit.

Bridgehampton

Drive through Bridgehampton and you will be struck by the modern amenities set against an agrarian landscape, formerly home to a booming potato farming community. I never leave Bridgehampton without stopping by Candy Kitchen. The luncheonette looks like it's straight out of the 1950s and has been featured in shows like Succession (it is allegedly where Kendall Roy was told he was next in line for Waystar as a child). It may seem like somewhere you’d purchase a burger and shake, but hiding on the menu is authentic Greek cuisine made by the first-generation family that owns it. Almond has been around since 2001 and has established itself as the scene for market driven, French inspired dishes with a twist ever since. On the weekends, you can find the bar area bursting with local energy.

Part of the rich history of the East End is its involvement in equine sport. You’ll pass plenty of farms on your way through, but if you are looking to see animals, I recommend driving past Swan Creek on Halsey Lane where you’ll see horses grazing in the pastures. If you happen to be around for Labor Day Weekend, The Hampton Classic Horse Show will also be in full swing. This week-long event is open to exhibitors for free, and allows you to see equestrians in action. You can purchase tickets to the show’s main event, the Sunday Grand Prix, online as well. Growing up, I had a loving admiration for the Children’s Museum East End (CMEE). This institution, clearly geared towards the little ones, has loads of interactive activities and playrooms for kids like drop-in classes and a summer camp. After dropping the kids off at CMEE, drive to Channing Daughters Winery for a glass of pinot grigio made from grapes grown on Long Island. 

Sag Harbor 

Sag Harbor is known for its rich whaling history, and has been home to a number of artists and musicians over the years. It is bustling at all hours and is home to some of the best restaurants and activities in the Hamptons. For breakfast, Estia’s is a short drive away from Main Street and serves Mexican-inspired fare all day in their outdoor space. Down Main Street, you’ll spot Grindstone Coffee & Donuts, where Vietnamese coffee and artisanal donuts are the perfect power-up as you take on Sag Harbor. On the wharf, the smell of homemade waffle cones will lead you to Big Olaf’s—a childhood favorite for locals with a sweet tooth. A short drive out of the main village, Cappelletti is a local spot for Italian specialties. Their focaccia sandwiches are to die for, and most locals can recall a memory of scarfing down their famous baked ziti as a kid. A new kid on the block, Sag Harbor Tavern is a sister restaurant to Red Hook Tavern in NYC and serves the same famous Dry Aged Red Hook Tavern Burger; a welcome addition to the village. 

Among the regular slew of stores on main street, there are also some hidden gems that have been around since my childhood. Flashbacks is a clothing boutique, and is fondly remembered among locals as the place to entertain yourself in the splendor of the candy selection while your parents shopped. Kites of the Harbor has been run by the same mom and son duo for years. A favorite among kids and adults alike, you’ll find rare toys and goofy gifts on the shelves. The family that runs the place is hilarious and extremely knowledgeable, so make sure to stop for a chat while shopping. Transport yourself back to the 1920s at Sag Harbor Variety Store—It’s been the same since my great grandma shopped there. Most people refer to it as ‘the 5 & 10’, but unfortunately, the crafts, toys, games and home goods are no longer just a few cents. Down a side street you’ll find Blooming Shells, a crystal and sea shell shop that can keep you occupied for hours looking at each special treasure. 

If you are a bookworm, or just love the smell of newly bound hardcovers, Sag Harbor Books might be the spot for you. You can pick up a new beach read and support local book sellers at the same time. After losing the historic Sag Harbor Cinema to a fire in 2016, the historic movie theater was rebuilt into a local hotspot. With few theaters in the area, the reconstruction was much needed. Now, you can catch new releases as well as vintage films, and grab a cocktail at the rooftop bar. Said by locals to serve the best dirty martini in the Hamptons, The American Hotel is a bustling restaurant by day, and a lively bar by night. There, you can find locals, celebrities, and tourists enmeshed in conversation over a martini—extra dirty please. To locals, Murf’s Backstreet Tavern is a townie bar during the off season, but on summer nights you might just spot Jimmy Fallon among the regular cast of characters.

Shelter Island

Off the beaten path (and by that I mean a short ferry ride away from Sag Harbor) Shelter Island is a hidden gem for a day of fun and good eats in the Hamptons. I like to use Sunset Beach Hotel as my home base when I head to the island, and park at the public beach out front. Lavish in the quiet bay water, rent a paddle board or take a bike around the area. After working up an appetite, walk straight from the beach to the hotel and eat at their restaurant which gives you a gorgeous view of the bay. After trying their fresh seafood (and the delicious fries) the bar is just steps away pouring wine and aperol spritz by the boatload.

East Hampton 

East Hampton is one of the larger villages in the Hamptons, and there is plenty to see. For a weekend lunch outing, I like to stop at one of the only BBQ joints in the area, TownLine BBQ. They serve comfort food specialities that rival the South, and the down home decor might have you thinking you crossed through a portal into another state. On the weekends, the village hosts the East Hampton Farmer’s Market which has everything from fresh pastries to my personal favorite, pickles on a stick.

With so many wineries in the area you might miss out on Sagaponack Farm Distillery, a distillery located on the same land the crop used to make their liquors is grown. With a long history of potato farming in the Hamptons, you’ll want to try one of their house made vodka cocktails in the tasting room. There is still more art to be discovered in East Hampton at the LongHouse Reserve, a product of the mind of artist, collector and textile designer Jack Lenor Larsen. The sprawling property is open to the public and houses an outdoor sculpture garden as well as art programs and plenty of opportunities for relaxation. Harper’s Books is known for their rare collection of books that can range anywhere from $300 to $10,000. This summer, they are also hosting 36 Paintings, a free art exhibition with works from contemporary artists across the country in their retail space. 

Shopping is highly encouraged in East Hampton, with almost all the big name luxury stores like Prada, Loewe, Balenciaga and Chanel just steps from each other. Streetwear legend Eric Emmanuel recently celebrated the opening of a pop-up for his brand in the village, which you can visit this summer. Known for his take on the classic basketball short, Emmanuel brings exclusive color ways and styles to serve his summer clientele. Emmanuel created his retail space in collaboration with John Margaritis, a Southampton local turned creative mastermind behind studio New York Sunshine. Margaritis started his now worldwide brand catered toward the surfing community in a small shop off the beaten path in Southampton. The nautical themed summer pop-up is a can’t miss.

Amagansett

Amagansett is my favorite spot for an early evening agenda that will most likely keep you out until the early morning hours. Coche Comedor is a Mexican inspired spot where inside, you’ll be greeted by bright colors and graffiti alongside your tacos and tequila. Just a step away–literally–is La Fondita, a Mexican street food spot great for takeout or a quick bite in their outdoor space. Doubles is a Caribbean inspired spot serving roti, sandwiches and delicious smoothies. You can grab your order and enjoy it on the tables right outside in Amagansett Square. 

Although Stephen Talkhouse has blown up in recent years (you can tell by the lines that often dominate the whole street of Amagansett), in its heyday it was a place for locals to enjoy a booming music scene with artists like Patti Smith and Billy Joel performing. To this day, it still boasts great music and long nights of fun. If you find some music you like at Talkhouse, down the street is Innersleeve, a record shop that is packed to the brim with new and vintage records.

Montauk

We have reached the end of our Hamptons trip. On the easternmost part of Long Island is Montauk, a lively town with roots in surfing, fishing and the arts. This area becomes more crowded every year as newcomers set up camp on its sandy shores. Although this restaurant has been featured in countless guides to the Hamptons, I would still recommend you grab a bite at Lunch for their famous lobster roll and a picture under their red, white and blue awning. 

If you want to skip all the fluffy stuff and hang like a local, start by watching the surfers at Ditch Plains beach. If you’re feeling adventurous you can check out Camp Hero, an old military base with a somewhat dubious history. Legend has it, the base was home to the infamous conspiracy of The Montauk project, a series of experiments in the realm of psychological warfare and time travel, said to be the basis of Netflix hit ‘Stranger Things’. The Ranch is a functioning horse farm as well as a contemporary art oasis. The property has a wide range of historical significance dating back to the 1920s—when Theodore Roosevelt trained rough riders there. Art consultant Max Levai, saw the beauty of the place back in 2020 and turned part of the property into an exhibition space and outdoor gallery. The Ranch has a rotating calendar of exhibitors that you can find on their website.