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DESTINATION GUIDE: THE HAMPTONS, NEW YORK

By 09.07.18. One Comment

Every summer, people from New York and beyond flock to The Hamptons to escape the city and settle into a slower pace for summer. This string of coastal towns located on the South Fork of Long Island is made up of beautiful cedar shake covered homes, blooming hydrangeas, incredible restaurants, the best shopping, and of course, beaches. Whether you want a laid-back getaway or want to hit up the Hamptons social scene, there’s plenty to do for everyone. And while summer is the most popular time to go, visiting in spring and fall can be great, too, with way less crowds. Below, we’re sharing all the best places to stay, eat, shop and things to do on your next trip out East.

PACK

STAY

RENT A HOUSE
Hamptons house.

AIRBNB / OUT EAST

A great option for finding a place to stay in The Hamptons is renting a home. Airbnb is a great place to start with a huge selection of weekend and weekly rentals. I have stayed in this Airbnb rental in Southampton, and couldn’t recommend it more (great location, great host, and that pool!!!). For longer term (monthly or summer long) rentals, check Out East. And please invite me.

BARON’S COVE
Baron's Cove, Sag Harbor

BARON’S COVE | Sag Harbor
31 W. Water St., Sag Harbor, NY 11963

Located on the harbor and just a short walk from Main Street, Baron’s Cove makes a great place to stay to experience Sag Harbor and The Hamptons. The hotel has 67 guest rooms, a restaurant with water views, a saltwater pool, tennis court, fitness room, spa services, and complimentary beach service and transportation. (Image via Baron’s Cove.)

The 1770 House
1770 House East Hampton

THE 1770 HOUSE | East Hampton
143 Main St., East Hampton, NY 11937

This former home was converted to an inn in 1770 and is still serving guests today with six beautiful rooms and a carriage house. The historic colonial property also has two dining options – a main dining room with a seasonal patio with a fine dining menu, and a casual downstairs tavern with traditional pub food. The inn and its restaurants are a celebrity favorite!

THE CROW’S NEST
Crow's Nest Montauk

THE CROW’S NEST | Montauk
4 Old West Lake Dr., Montauk, NY 11954

This hotel and restaurant located on Lake Montauk exudes a casual summer vibe, done by Sean MacPherson, the hotelier behind some of my favorite NYC spots (The Bowery, The Marlton, The Ludlow, etc.). Guests enjoy complimentary bikes, paddle boards, fire pits under string lights, and stunning sunset views over the lake, plus lots of other little details that make this property a favorite.

GURNEY’S MONTAUK
Gurney's Resort and Seawater Spa, Montauk

GURNEY’S | Montauk
290 Old Montauk Hwy, Montauk, NY 11954

Gurney’s Resort and Seawater Spa is Montauk’s only oceanfront resort and it’s open year-round. It features 146 rooms, suites and cottages, all with a sprawling ocean view and just steps to a private beach. Spend the day lounging in one of the beach cabanas, make a stop in the spa, and in the evening, enjoy the Italian fare over panoramic ocean views at the hotel’s restaurant, Scarpetta Beach.

THE MAIDSTONE
The Maidstone

THE MAIDSTONE | East Hampton
207 Main St., East Hampton, NY 11937

The Maidstone feels more like a home than a hotel (in a good way!), but this chic little property just steps from East Hampton Village actually boasts 19 rooms, all individually designed with their own charm. Enjoy your coffee in an adirondack chair on the front lawn or take the bikes for a spin around East Hampton.  When you’re hungry (or thirsty), head to the restaurant for a meal in the sunroom or have drinks out in the garden, bar or lounge.

THE SURF LODGE
The Surf Lodge, Montauk.

THE SURF LODGE | Montauk
183 Edgemere St., Montauk, NY 11954

The Surf Lodge is a happening hotel located on Fort Pond in Montauk. The accommodations are casual and beachy, with hammocks, whitewashed floors and surf-themed decor. Hang out at the beach bar, take the hotel bikes for a ride, or grab a bite to eat in the restaurant. The hotel often has live music and on the weekends there’s sure to be a fun, rowdy day party.

TOPPING ROSE HOUSE

TOPPING ROSE HOUSE | Bridgehampton
One Bridgehampton – Sag Harbour Turnpike, Bridgehampton, NY

This beautiful 22-room inn located in Bridgehampton is open year round and offers a farm-to-table Jean-Georges restaurant, spa services, a complimentary shuttle to the beach, a heated outdoor pool and house vehicles by Lexus. Book through The Hollyday to receive VIP amenities and upgrades at this partner property! (Image via Virtuoso.)

EAT + DRINK

COWFISH
Cowfish Hampton Bays

COWFISH | Hampton Bays
258 E Montauk Hwy, Hampton Bays, NY 11946

Cowfish is located on the water in Hampton Bays which you’ll pass through as you drive into The Hamptons. It’s right off the highway and is a perfect spot to stop for lunch or dinner as your driving in. It’s a casual vibe and they have a great outside bar. It’s also a great place to catch the sunset. There’s lots to choose from on the menu but I love the fish sandwich and their sushi. It’s a reasonable distance from Southampton or Watermill so add it to your list of dinner spots if you’re staying in one of those nearby areas.

THE CROW’S NEST
The Crow's Nest, Montauk

THE CROW’S NEST | Montauk
4 Old West Lake Dr., Montauk, NY 

The restaurant at The Crow’s Nest is probably my favorite restaurant out East and that’s saying a lot because there are so many… it’s hard to choose! Definitely plan for a dinner here one night. The atmosphere is upscale but rustic and the New American/Mediterranean inspired menu is delicious. (I recommend the seafood pasta.) They don’t take reservations, so get there early, put your name on the list and head down to the bar by the water to get a cocktail while you wait.

DURYEA’S LOBSTER DECK
Duryea's Lobster Deck

DURYEA’S LOBSTER DECK | Montauk
65 Tuthill Road, Montauk, NY 11954

Duryea’s looks more like something you’d find in the Mediterranean, rather than Montauk. It’s beach-club chic atmosphere combined with its stellar location right on Fort Pond Bay makes it the perfect setting for a delectable, upscale seafood lunch or dinner. Enjoy the lobster roll, fresh oysters or crab legs and their huge family style size salads.

GEORGE’S LIGHTHOUSE CAFE
Montauk Point Lighthouse

GEORGE’S LIGHTHOUSE CAFE | Montauk
1999 Montauk Point State Parkway, Montauk, NY 11954

Don’t miss a trip out to the very end of Long Island to see the lighthouse, and while you’re out there, stop by George’s – a casual, lodge type spot located adjacent from the lighthouse with stunning views of the Block Island Sound. There are TVs, a big fireplace, a welcoming bar and a sprawling patio with games and things to entertain you for an hour or two while you soak in the views.

LE BILBOQUET
Le Bilboquet Sag Harbor

LE BILBOQUET | Sag Harbor
1 Long Wharf, Sag Harbor, NY 11963

The beautiful waterside outpost of this NYC, Dallas and Atlanta french bistro draws a fancy crowd. Go for lunch or an upscale dinner and sit outside overlooking the wharf. Take a break from seafood and order the cajun chicken, their signature dish.

THE LOBSTER ROLL
The Lobster Roll restaurant.

THE LOBSTER ROLL | Amagansett
1980 Montauk Highway, Amagansett, NY 11930

The Lobster Roll Restaurant sits on the side of the highway and usually has a line at the door before it even opens. The iconic sign says “LUNCH” even though it serves dinner, too. So no matter what time of day, you can satisfy your lobster roll craving at this Hamptons favorite.

LT BURGER
LT Burger Sag Harbor

LT BURGER | Sag Harbor
62 Main Street, Sag Harbor, NY 11963

This is a family favorite in Sag Harbor – the Hamptons version of a good old fashioned burger joint. Top your order off with some fried pickles, or choose from an assortment of french fry styles (skinny fries, waffle fries, sweet potato fries!) and wash it down with a “Rated R” shake made with your choice of liqueur.

NAVY BEACH
Navy Beach

NAVY BEACH | Montauk
16 Navy Road, Montauk, NY 11954

Location doesn’t get much better than this restaurant that sits on 200 feet of private beach in Montauk. Reserve a table outside by the water, or dine inside the nautical themed restaurant with a sprawling antique wooden bar. It’s open for both lunch and dinner, and a great place to watch the sunset.

THE RESTAURANT AT THE MAIDSTONE
The Restaurant at The Maidstone

THE RESTAURANT AT THE MAIDSTONE | East Hampton
207 Main Street, East Hampton, NY 11937

Enjoy breakfast, lunch, dinner or even a late-night snack at the Restaurant in the Maidstone hotel. I suggest having a cocktail in the lobby lounge and then enjoy your meal in the sunroom overlooking the pond our out back in the garden.

RUSCHMEYER’S
Ruschmeyers

RUSCHMEYERS | Montauk
161 2nd House Road, Montauk, NY 11954

Ruschmeyers is a Hamptons favorite and a great place for a casual summer dinner or weekend brunch. Sit outside at a picnic table under the string lights, and if you’re lucky it might be movie night! There’s also a firepit, ping pong tables and other yard games. A great spot for kids and adults alike.

SANT AMBROEUS
Sant Ambroeus Southampton

SANT AMBROEUS | Southampton
30 Main Street, Southampton, NY 11968

If you know this delicious little Italian spot for its locations in NYC or Palm Beach, this one is no different. Coffee, cocktails, pasta and gelato – you’ll find it all here. If you’re sitting down for a meal, ask for a table in the charming little side courtyard.

SCARPETTA BEACH
Scarpetta Beach, Montauk NY

SCARPETTA BEACH | Montauk
290 Old Montauk Highway, Montauk, NY 11954

For a delicious Italian meal overlooking the ocean in Montauk, head to Scarpetta Beach at Gurney’s and order the classic dish they’re known for – spaghetti tomato and basil. Start your evening with cocktails outside around the fire pit on the deck before heading to your table for dinner.

SOUTHAMPTON PUBLICK HOUSE
Southampton Publick House

SOUTHAMPTON PUBLICK HOUSE | Southampton
62 Jobs Lane, Southampton, NY 11968

Publick House is a local brewery and a great spot to grab a house made beer and catch a sports game on tv, with seating both inside and out. Stop by for happy hour after shopping in Southampton or check out their live music lineup here. (Image via @southamptonpublickhouse.)

THE SURF LODGE
The Surf Lodge, Montauk

THE SURF LODGE | Montauk
183 Edgemere Street, Montauk, NY 11954

The restaurant at The Surf Lodge is definitely a Hamptons hotspot with it’s open air setting inside, the lively deck with water views and live music. It’s the perfect casual spot to enjoy some fresh seafood and live music. And on the weekends it gets rowdy with concerts on the deck, so check the schedule here and plan accordingly.

TUTTO IL GIORNO
Tutto Il Giorno, Southampton

TUTTO IL GIORNO | Southampton
56 Nugent Street, Southampton, NY 11968

For an upscale, Hamponts-chic Italian dinner, book a table at Tutto Il Giorno in Southampton (or its original location in Sag Harbor). The restaurants were designed by Donna Karan’s daughter, Gabby Karan De Felice. The interior is stunning, but if the weather’s nice, request a table outside under the string lights. The Southampton location is also open for lunch.

WOLFFER ESTATE VINEYARD
Wolffer Estate Vineyard

WOLFFER ESTATE VINEYARD | Sagaponack
139 Sagg Road, Sagaponack, NY 11962

Definitely stop by the beautiful Wolffer Estate during your visit to the Hamptons for a taste of their wines. You can reserve a table inside or overlooking the vineyard to sit and enjoy a glass of wine and small plates, or schedule a full tour and tasting. If you don’t have time to visit the winery, you can stop by their Wine Stand (located at 3312 Montauk Highway; open daily) which still has views of the vineyard (and live music) to enjoy a quick glass or get some vino to-go.

SHOP

LoveShackFancy Sag Harbor
R.R.L. & Co.

SOUTHAMPTON

In the little downtown of Southampton, you’ll find shops like Homenature, Blue & Cream, Club Monaco and One Kings Lane. Don’t miss Tate’s Bake Shop, where you can pick up some of those freshly baked thin chocolate chip cookies.

EAST HAMPTON

On Main Street in the village of East Hampton, hit up Obligato, RRL & Co., Reformation Beach House, Intermix, Aerin, Zimmermann, Book Hampton and more.

SAG HARBOR

In Sag Harbor, stop by LoveShackFancy for feminine, flowy dresses, Jayson Home for unique interiors and the Goop pop-up.

SEE + DO

Sag Harbor, NY
Coopers Beach
Hampton Bays Marina
Montauk Lighthouse

MONTAUK LIGHTHOUSE

Take a drive out to the end of the island to Montauk Point State Park to see the Lighthouse, a national historic landmark. The views are stunning and you can take a trail down the beach for a great photo-op. There’s also a museum at the lighthouse if you want to learn a little about it’s history.

GO TO THE BEACH

There are multiple public beaches to choose from, but check out Coopers Beach in Southampton (voted one of America’s most beautiful in 2017); Two Mile Hollow Beach in East Hampton usually less crowded than the main beach nearby), or Kirk Park Beach in Montauk (free parking!).

GOLF

There are lots of golf courses out on the East End, but many of them are members only. Check out this website for a list of courses open to the public.

HORSEBACK RIDING

Equestrian life is huge in The Hamptons, with stables and immaculately kept horse farms everywhere. Check out Deep Hollow Ranch in Montauk which offers trail rides along the beautiful coastline.

HOUSE HUNTING

Driving around looking at the beautiful homes of The Hamptons is an activity in and of itself! Take a drive down Gin Lane and Meadow Lane in Southampton (where you’ll pass the house from “Something’s Gotta Give”) and Ocean Road in Bridgehampton for a look at some of the area’s most sensational properties.

KNOW

The Hamptons

WHEN TO GO

Obviously, summer is the most popular time to visit this string of beachside towns, but visiting in fall and spring can be great, too! It may not be bathing-suit weather, but you can expect way less crowds and a more relaxed vibe.

HOW TO GET THERE

There are plenty of ways to get out to The Hamptons.

One of the easiest ways is to fly into one of the NYC area airports and rent a car. The drive from Manhattan to Southampton is 87 miles, about 2.5 hours (depending on traffic). From Manhattan to Montauk, the eastern top of the island, is about 120 miles, or 3 hours. It can be nice having a car out there because everything is so spread out.

If you want to forgo the rental car, hop on The Hampton Jitney, a motor coach bus that runs from Manhattan to Montauk throughout the summer for about $30 bucks.

There are a few small airports in The Hamptons if you are flying in private, including East Hampton Airport, Montauk Airport, and Westhampton Beach Airport.

If you want to helicopter (or sea plane) out from NYC, check out Blade, which runs back and forth from The Hamptons to the city all summer. You can buy one seat, crowdsource a flight, or charter a private trip whenever you want. Basically Uber with helicopters (and a much heftier price tag), but it beats the traffic and your trip starts out in their cushy lounge.

HOW TO GET AROUND

The Hamptons are really spread out, so you’ll definitely need a mode of transportation other than walking or biking if you don’t have your own car there. Thankfully, Uber and Lyft are now available Hamptons-wide, after being unavailable in East Hampton for a couple years.

Contact The Hollyday here to get started planning your trip to The Hamptons!

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