Overall, it’s a series of hamlets and villages on Eastern Long Island that blend upscale Americana, stunning marinas, and sprawling vineyards with quaint farm stands, nature preserves, seafood shacks, and surf beaches. And it all ends with a majestic lighthouse overlooking the Atlantic Ocean.
How I Got There and Where I Stayed:
The main Hamptons towns are Southampton, East Hampton, and Montauk (about 100 miles east of NYC). Surrounding these towns are places like Amagansett and Sag Harbor. And each has its own charm and identity. For instance, you can't drive through the center of East Hampton without viewing one of its iconic landmarks, the famous Hook Windmill.
During my visits, I’ve stayed with friends, but many tourists rent vacation homes for their stay. There are also resorts, boutique hotels, B&Bs and motels for every budget.
I love the pink bicycles and chairs at Maidstone in East Hampton, but I have friends that are loyal to Gurney’s, Ruschmeyer’s, and Sole East in Montauk.
And getting to the Hamptons from New York is easy. Public and private transportation options include car, bus (Hampton Jitney), train (Long Island Railroad), or even helicopter (definitely not in my budget!).
What I wore:
Summertime in the Hamptons is a pleasant mix of Americana couture (picture Ralph Lauren on a yacht in Sag Harbor) and relaxed glamour, including linen sundresses, summer whites, crisp stripes and classic silhouettes.
But the further east you travel, the more you’ll feel the influence of bohemian artists and surfside chill. Sort of like traveling from Manhattan’s Upper East Side to Brooklyn. The vibe gets more casual along the way!
What I did:
I shopped and ate my way through Southampton and East Hampton. And I spent all of my time in boats and on the beach in Montauk.
What I ate/drank:
I’ve made several trips to the Hamptons over the years since it’s just across the Long Island Sound from my home in Westport, Connecticut. Here are a few highlights from my visits (traveling from West to East):
Southampton:
· Rumba (Island cuisine with a great waterfront locale)
· 75 Main (delicious salads for a light lunch before hitting the beach)
· Milkshakes at Sip ‘N Soda (my younger brother Charlie’s favorite)
East Hampton:
Babette’s is my favorite brunch spot. It has lovely outdoor seating and plenty of vegan and vegetarian options. It’s a perfect spot to take a break from shopping on Main Street, and the hibiscus tea and avocado toast are a delicious treat!
But if you’re looking for something a bit more decadent, grab a sweet treat at Dylan’s Candy Bar or donuts at Dreesen’s.
Amagansett:
You haven’t been to the Hamptons if you don’t stop for fresh seafood at Clam Bar and Lunch. The two restaurants are across the highway from one another.
Plan to stop at Lunch on your way to Montauk and at Clam Bar on your way home. You won’t regret it!
Montauk:
Plenty of fresh seafood options, but head to Ditch Plains and grab some beach fare at Ditch Witch. Or indulge in ice cream at John’s Drive-In and end the evening with live music at the Surf Lodge.
Social media musts:
The Hamptons are made for Instagram! You can glam it up with a summer chic dress and designer handbag for brunch in Southampton/East Hampton or throw on a bikini and ride the waves in Montauk.
No matter where you go, there will always be a stunning backdrop!
My travel playlist:
Uptown Girl – Billy Joel (he and ex-wife Christie Brinkley are famous residents of the Hamptons)
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