How to Spend Two Fancy but Affordable Days in the Hamptons
Take a self-guided tour of lavish estates, spot celebrities in the wild, and lounge on one of the most beautiful beaches in the country without bleeding your bank account
The depictions of the Hamptons in TV shows and movies may seem grandiose, but it’d be a lie to say they’re far from reality. From sweeping drone shots of oceanfront estates to vintage convertibles rolling down Further Lane and Dune Road to summer crowds dripping in designer accessories, media portrayals lean into the stereotype of exorbitant wealth in these storied Long Island enclaves because they’re completely accurate.
As a summertime playground for executives, celebrities, and socialites, the Hamptons thrive on exclusivity and over-the-top experiences. In a land of $50 lobster rolls and private soirees with endlessly flowing champagne, the unspoken motto of the Hamptons lifestyle is simple: If you are going to do it, do it with style and substance.
We’d all like to keep up with the billionaire summer beach-house crowd, but you don’t have to own a Bentley or drain your savings to enjoy a lavish escape to the East End. With a little strategy and an open-minded outlook, you’ll find plenty of ways to indulge without overdoing it. No matter your usual routine, sometimes you’re in the mood for a towering seafood display or a $30 Aperol spritz. Here’s how to have a refined (but not wildly expensive) getaway in the Hamptons, on your own monetary terms.
Who I am: I’ve lived and breathed the Hamptons for over 35 years. My grandparents originally came to Sagaponack to scout for potato farmland (if only they made the purchase). Instead, they made their home in the village of North Haven on the outskirts of Sag Harbor. My dad was a co-owner of the famous nightclub Stephen Talkhouse, so the Hamptons always maintained relevance for me. Over the years, I’ve seen more than my fair share of extravagance and wealth and have cups of tea overflowing with the scandalous tales I’ve heard and witnessed firsthand. As a freelance food and travel writer and owner of my own media and event production company, I’ve been blessed with the opportunity to be hosted at and attend some of the Hamptons's most coveted restaurants, galas and benefits, spas, hotels, and so much more. I’ve been to hundreds of private parties at lavish estates, rubbing elbows with celebrities, socialites, and the summering elite. Though my home in the Hamptons may not be “South of the Highway,” I like to think of my lifestyle as “understated East End luxury.”
Before you go
How to get there: If you’re coming from New York City, splurge just a touch on your trip out east with the Hampton Ambassador bus by Hampton Jitney. This bus makes stops along Lexington Avenue and in Queens for those connecting from JFK or LaGuardia airport. The Hampton Ambassador bus offers generous amounts of legroom, the option to reserve your seat in advance, and a complimentary glass of wine or coffee. I recommend heading out east after 10 a.m. to avoid the inbound Hamptons traffic. If money isn’t an issue and you want to save the headache of being stuck in traffic on the LIE, BLADE offers helicopter and seaplane flights from Manhattan to East Hampton Airport, starting at $1,095/seat one way.
Only select areas of the Hamptons are walkable, and you’ll need a mode of transportation to get from one town or village to the next, as Montauk Highway is not pedestrian friendly. If you choose to rent a car, rent it halfway to the East End, and take the train from NYC to Ronkonkoma. You’ll have a variety of car company rental options adjacent to the nearby Long Island MacArthur Airport.
Insider tip: Sag Harbor has the most vibrant late-night scene, followed by Bridgehampton and Amagansett. Most restaurants also stop serving dinner by 10 p.m., with many kitchens closing as early as 9:30 p.m. even in summer. If you’re driving, pop into Riverhead on your way out east to explore the Tanger Outlet shopping mall for some designer finds that are far more affordable than shopping in East Hampton or Southampton, whose Main Streets are looking more like Rodeo Drive and Madison Avenue than ever before. Those storefronts usually do not have sales until the third week of August.
WHERE TO STAY
Two Slightly Fancy Days in the Hamptons
First thing to do when you get to town: Stock up your fridge and shelves with fresh, local produce from any one of the farm stands and specialty markets. Check out Amber Waves Farm in Amagansett for their wide selection of ready-made meals, Carissa’s Bakery in Sag Harbor and East Hampton for their freshly baked breads and baked goods (their salty soured pickled rye bread is a staple in my kitchen), and the newly renovated Sagaponack General Store for their malted chocolate chip cookies and cinnamon rolls with sticky caramel. The General Store is also a great stop for picking up freshly picked flowers.
Day 1: Shopping, strolling, and celebrity spotting
Morning
- Kick off the morning at Jack’s Stir Brew in Sag Harbor (there’s also a location in Amagansett). Try their signature honey cinnamon Happy Jack latte paired with a freshly baked blueberry crumble muffin. It’s also a great grab-and-go spot with seating inside and outside.
- Stroll through Sag Harbor Village and explore the varied boutiques. Sag Harbor is known for their mix of locally-owned shops. This is also where I’d recommend purchasing gifts for loved ones at home. Visit The Wharf Shop for everything from handcrafted jewelry to toys for kids, and head to Sage and Madison for unique fashion pieces, tabletop gifts, and a mix of signature pop ups throughout the summer season.
- Take a scenic walk through Elizabeth A. Morton Wildlife Refuge in Noyack and connect with the local wildlife. Spot wild deer, turkey, chickadees, falcons, osprey, and bring ample amounts of bug spray, because the deeper you go into the trails, the more aggressive the bugs can be.
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Midday
- Enjoy a late lunch at Smokin’ Wolf BBQ in East Hampton off Montauk Highway, one of the area’s best kept secrets and an affordable and fun place to eat since the portions are so generous. Order the cornbread basket and cowgirl quesadillas with guacamole, mango salsa, and caramelized onions. They have indoor and outdoor seating, but you could also get your order to go for a picnic at the park or the beach.
- Tour the Pollock-Krasner House & Studio tucked away in Spring, which is still covered in paint splatter from Jackson Pollock himself and where he created some of his most famous work.
- Stroll through Amagansett Square, which has ample space for young kids to run around under shade. Explore the local shops for people of all ages, and catch an outdoor yoga class or community event. Some of my favorite boutique shops in the square include New York based lifestyle brand Brunch, Ulla Johnson for signature styles inspired by destinations around the world, and Cavaniola’s Gourmet for the finest cheeses and jams—a perfect stop for a housewarming gift.
Evening
- Catch a show or art opening at Guild Hall, East Hampton’s cultural cornerstone for theater, film, and visual art. Right now, you can see the NYC Ballet or Celebrity Autobiography with Christie Brinkley and Richard Kind.
- Grab dinner at the iconic Nick and Toni’s, where you can easily spot a celebrity or two on any given night (past diners include Jennifer Lopez, Paul McCartney, and Tom Hanks). Try one of their famous wood-fired Mediterranean dishes paired with their crispy fried zucchini chips, a house favorite.
- Take a late night beach stroll on Georgica Beach, just past the storied Grey Gardens estate on West End Road. The estate is now privately owned by fashion designer Liz Lange.
Day 2: Stunning beaches, fresh linguine, and art
Morning
- Kick off the morning at the original Tate’s Bake Shop in Southampton. Grab some coffee and a couple bags of their iconic crispy chocolate chip cookies while in town (and plan on coming back later to treat yourself to one of their ice cream cookie sandwiches.
- Stroll through Southampton Village. Pop into shops like Hildreth’s, Flying Point Surf & Sport, Topiaire Candy Shop, and Aloof Icon. Take in the natural scenery at Agawam Park where you may spot a flock of ducks and several swans floating by along the lake.
- From Agawam Park, turn down Pond Lane and onto First Neck Lane and Meadow Lane for a self-guided tour of some of the most lavish Hamptons estates. Pass by Cryder Beach and take Meadow Lane all the way down to Shinnecock East County Park past Dune Beach.
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Afternoon
- Turn back down Meadow Lane, and spend the early afternoon at Coopers Beach in Southampton, continuously rated as one of the most beautiful beaches in the U.S. Here, you can grab food like fish tacos, sandwiches, and fries at Coopers Beach Shack, and there are bathrooms and outdoor showers onsite.
- Set in Water Mill on Montauk Highway, the Parrish Art Museum showcases over 3,500 works including pieces from local artists like Roy Lichtenstein and Jackson Pollock. The building’s architecture also makes for a beautiful backdrop for photos especially with its overhanging roofline.
Evening
- Head just west of the Shinnecock canal and enjoy early evening cocktails at Amalfi in Hampton Bays. Catch a live DJ set with a stunning sunset as the backdrop. This spot is favored by locals, who particularly enjoy their aperitivo hour at their indoor and outdoor bar from 4 pm to 6 p.m. during the week.
- Visit Tutto Il Giorno for a candlelit dinner and fresh pasta (try my favorite: the linguine with clams and house-dried tomatoes). I particularly love to dine al fresco in the front of the restaurant and to practice my Italian with the staff, many of whom hail from Italy.
- Catch a live show at the Westhampton Beach Performing Arts Center. Open year round, shows range from stand-up sets by Saturday Night Live stars to an evening of storytelling from the beloved humor writer David Sedaris.
If you have three days
All of the above, but add…
- Head further east down the Napeague stretch and enjoy an outdoor lunch at the Clam Bar. It’s first-come-first-serve seating, and must-try dishes include their loaded cold lobster roll, clam strips, and lobster bisque.
- Have a spa day Gurney’s in Montauk, and if you’re interested, make time to stop by the resort’s seasonal Dolce & Gabbana pop-up.
- Head to the beachfront hotel Marram for an evening bonfire and beach walk. Pair it with a late night dinner and live music at Westlake Fish House.
If you have four days or more
All of the above, but add…
- Schedule an overnight visit to nearby Shelter Island. Take the South Ferry from North Haven; less than 10 minutes later, you’ll find yourself in a restful escape with no traffic lights in sight. Check in to the Pridwin, the sprawling retreat hotel which features a camp-like atmosphere with a plethora of outdoor activities like pickleball, a private beach, waterview pool, and lawn games like cornhole and croquet. Plan your visit around their midweek summer barbecues or Monday Movie Nights to add to the nostalgic charm. Spend your afternoons on Shelter Island kayaking on Coecles Harbor followed by an Aperol spritz at the energized Sunset Beach. Be sure to arrive early to grab parking in front or keep your vehicle at The Pridwin, and take a brisk walk along Shore Road.