Insider’s Guide to The Hamptons
The Hamptons have been woven into the fabric of my life for as long as I can remember, first as a young woman chasing beach days and rosé at sunset, and later as a mother watching my two boys grow up racing barefoot across the dunes. It is my slice of America, the one place that still feels completely like home.
Whether you're planning a romantic getaway, a family week by the beach, or simply curious about the East End beyond what you have seen on Instagram, the Hamptons deliver. Connect with me to plan your Hamptons getaway and unlock experiences that turn a good summer into a truly memorable one.
Need to Know
Before you arrive, there are just a few things worth knowing. The Hamptons are not one destination but a collection of villages, each with its own personality, Southampton polished and elegant, Sag Harbor endlessly charming, East Hampton effortlessly sophisticated, whilst Montauk still retains the wonderfully bohemian spirit that first made people fall in love with it.
Currency: The United States uses the US Dollar (USD). Cards are accepted virtually everywhere, though a little cash is handy for farm stands and smaller beach vendors. Tipping is customary and expected, generally fifteen to twenty percent at restaurants.
Airports: If travelling from outside New York, most people fly into JFK or LaGuardia and drive out East. East Hampton Airport (HTO) and Montauk Airport (MTP) welcome private aircraft for those wanting to skip the traffic entirely. Private plane and helicopter services also run seasonally from Manhattan and are a wonderfully glamorous way to arrive. We work with trusted suppliers to coordinate this for our clients.
Transportation: One of the great luxuries of the Hamptons is deciding how you arrive. Beyond private aviation, the Hampton Jitney remains the classic way to escape the city, while the Ambassador bus also offers regular service throughout the summer. The Long Island Rail Road offers a more leisurely, scenic journey out to the East End. Once you've arrived, I always recommend having a car, as the villages stretch much farther than many first time visitors expect.
Best time to visit: If you ask me, I will always say early June or September. The crowds thin, the light softens, and reservations become far easier to secure. Memorial Day through Labor Day is peak season, when every village is at its liveliest and the beaches are in full swing.
Ideal length of stay: Stay for a week if you can. The Hamptons reveal themselves slowly, splitting time between the beach clubs and boutiques of Southampton, the quiet charm of Sag Harbor, and the wilder, more bohemian energy of Montauk out at the end.
Where to Stay
Topping Rose House – Bridgehampton
One of the Hamptons' finest boutique hotels. Topping Rose effortlessly combines historic elegance with contemporary luxury. Mornings begin overlooking the property's working farm before breakfast at Jean-Georges, a ritual for me whenever I'm nearby.
Hedges Inn – East Hampton
Tucked away on James Lane, Hedges Inn feels wonderfully intimate. Recently redesigned, its thirteen beautifully appointed rooms offer a refined retreat just moments from Main Beach and the village centre.
Gurney's Montauk Resort & Seawater Spa
If your idea of the perfect morning is waking to the sound of crashing waves, this is where I would send you. Gurney's has been synonymous with Montauk for generations, with a legendary seawater spa and private beach.
Shou Sugi Ban House – Water Mill
Whenever life feels particularly hectic, this is where I escape.
The Japanese-inspired wellness retreat combines beautiful garden studios, restorative hydrotherapy rituals and a deeply seasonal culinary programme.
Faraway – Sag Harbor
Faraway perfectly captures the relaxed elegance of Sag Harbor.Harbour views, complimentary bicycles and an excellent Italian restaurant make it tempting never to leave.
LDV at The Maidstone – East Hampton
A Hamptons classic reimagined with unmistakable Italian flair. Open throughout the year, aperitivo in the garden followed by dinner is one of my favourite ways to spend a warm evening.
Montauk Yacht Club
Set across sixteen waterfront acres overlooking Lake Montauk, the Yacht Club feels more like a resort than a hotel, ideal for families spending long, leisurely days by the water.
Hotel Corduroy – Montauk
For those drawn to Montauk's surf culture, Hotel Corduroy strikes the perfect balance between laid-back style and modern comfort.
The American Hotel – Sag Harbor
If I could bottle the charm of Sag Harbor, it would look something like The American Hotel. Breakfast lingers well into the morning and the famous lobster omelette is almost obligatory.
The Roundtree – Amagansett
Quietly luxurious, The Roundtree is my recommendation for those seeking peace and privacy amongst beautifully landscaped gardens.
Private Home Rental
The Hamptons largely operate on a rental home basis, with most visitors booking a house by the week or month. That said, there is a growing collection of excellent hotels dotted across the region for those who prefer not to rent. If a rental is more your speed, I work closely with Sotheby's Realty in the Hamptons. Between my knowledge and my partners at Sotheby's we can guide you to the best village for what you are after and the best location within it.
Where to Visit
Southampton
A classic first stop, this affluent village appeals for its broad Atlantic beaches, walkable downtown, and genuinely tranquil atmosphere once you step off the main strip.
Bridgehampton
This refined hamlet is known for its manicured estates, summer polo matches, and the prestigious Hampton Classic Horse Show each August.
Water Mill and Sagaponack
Quiet and largely residential, shaped by preserved farmland, vineyard culture, and some of the region's best art and design destinations.
East Hampton
Home to big name shops and famous faces, East Hampton still holds pockets of classic, old world charm if you know where to look.
Sag Harbor
This village charms with its cobblestone streets, working harbor, and a pace that has grown busier over the years without losing its soul.
Amagansett
A quieter, more understated village between East Hampton and Montauk, known for its farm stands and laid back beach town feel.
Montauk
Known as The End for its position at the very tip of Long Island, this bohemian town revels in surf culture, golden hour bonfires, and serious dining.
What to Experience
Things to Do
Spend a sunset Friday at Wölffer Estate's Wine Stand in Sagaponack, with live music and rosé
Wander the sculpture garden and galleries at the Parrish Art Museum in Water Mill
Climb the Montauk Point Lighthouse, commissioned by George Washington himself in 1792
Join the Monday night drum circle at Sagg Main Beach in Sagaponack
Enjoy live music at Stephen Talkhouse in Amagansett
See a match at Polo Hamptons in Bridgehampton each July
Catch a sunset show at The Surf Lodge in Montauk
Learn to surf at Ditch Plains Beach in Montauk
Charter a fishing boat from Montauk, the Sportfishing Capital of the World
Bike the quiet country roads of the Hamptons, passing farm stands, historic homes, vineyards, and scenic landscapes around Bridgehampton, Amagansett, and East Hampton
Visit the farm stands along Montauk Highway, stopping for fresh berries, corn, pies, flowers, and locally grown produce
Best Beaches
Sagg Main Beach in Sagaponack is my personal favorite, wide white sand, dependably good surf, and a wonderfully local feel compared to some of the busier ocean beaches further west. Lifeguards are on duty by day, and there are restrooms, outdoor showers, and a food truck or two for when hunger strikes. What truly sets Sagg Main apart is the Monday evening drum circle that has been drawing crowds for decades, when the beach fills with drummers, dancers, and onlookers as the sun goes down. Bring a chair, arrive early for parking, and let the evening unfold around you.
Cooper's Beach in Southampton is the most photographed beach in the Hamptons and regularly ranks among the best beaches in the country. It comes with proper amenities, a bathhouse, restrooms, a concession stand, and chair and umbrella rentals for those who did not bring their own. Parking is not cheap and fills up fast on a summer weekend, so arrive early or plan to walk or bike over instead.
Where to Eat
Best Lobster Roll
The Lobster Roll ("Lunch") - Amagansett & Southampton
Dinner
Nick and Toni's - East Hampton
Duryea's - Montauk
Tutto il Giorno - Sag Harbor
Le Bilboquet - Sag Harbor
Calissa - Montauk
Alba Spiaggia - Montauk Yacht Club
Sant Ambroeus - East Hampton
The Bird - Montauk
Breakfast and Lunch
Pierre’s - Bridgehampton
Carissa's Bakery - East Hampton
Candy Kitchen - Bridgehampton
Sip 'n Soda - Southampton
SunLife Organics - Bridgehampton
Roadside & Casual Favorites
La Fondita - Amagansett
Fini Pizza - Amagansett
Bostwick's Chowder House - East Hampton
Sweet Treats
BuddhaBerry - Sag Harbor
Sundaes on Main - Bridgehampton
Cocktails & Sunsets
Wölffer Estate Vineyard - Sagaponack
Sunset Beach - Shelter Island
Dopo la Spiaggia - Sag Harbor
Bar Almond - Bridgehampton
Exclusive Lady Stephanie Perks
When you book your escape through me, I make sure you are looked after with these special touches at each property.
✧ Upgrade on arrival, subject to availability
✧ Daily breakfast for up to two guests per bedroom
✧ $100 USD equivalent Resort or Hotel credit to be utilized during stay
✧ Early check-in / Late check-out, subject to availability
Trips to Add On
Shelter Island
A short ferry ride from North Haven or Greenport delivers you to a slower, wilder version of the East End, ideal for a single quiet day away from the crowds.
The North Fork
Long Island's quieter, more agricultural sister across the bay, all vineyards, oyster farms, and small town main streets.
Block Island
A ferry from Montauk or a short flight brings you to this sleepy Rhode Island island, all Victorian farmhouses and bluffs.
New York City
Bookending a Hamptons stay with a night or two in Manhattan on either end is the classic pairing.