The Cool Girl Travel Guide: What to do in the Hamptons

There’s a taboo rule amongst NYC natives who plan on spending some time out east for the summer- befriend somebody that has a house out in the Hamptons. Luckily, I can cross that off of my list. A couple of my close friends and I headed out east for the weekend and spent quality time sipping local wine, eating great food, and relaxing. Since there is so much to do, I put together a quintessential itinerary for your next chic Hamptons/Montauk retreat.



The Maidstone Hotel

Swanky, scandi-style boutique hotel right in the heart of the Hamptons.

207 Main St, East Hampton, New York


The Chequit

Offering a sun terrace and views of the sea, it’s no wonder this boutique Inn was rated among the top luxury hotels in New York according to U.S. News & World Report.

23 Grand Ave, Shelter Island Heights, New York


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Wölffer Kitchen Sag Harbor

I made sure I was able to get reservations here because it definitely lives up to the hype. The menu is contemporary American with a fresh and healthy “rosé-inspired” cuisine. Make sure to get the mushroom truffle flatbread and the lobster salad wrap- both to die for.

29 Main St, Sag Harbor, New York


Maison Vivienne

A new French restaurant created by Michelin Star Executive Chef Wolfgang Ban is about to be your new favorite date night. The modern black and white interior features cathetral ceilings and del fresco dining. Order the roasted heritage chicken for 2, carved table-side.


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Wölffer Estate Vineyards

Gorgeous setting resembling a classic Italian style villa. Enjoy a great atmosphere and wine tasting on the patio that overlooks the vineyard. Make sure to order the “summer in a bottle” rosé.

139 Sagg Rd, Sagaponack, New York

Best Social Scene


The Surf Lodge

Best boozy brunch – need I say more?

183 Edgemere St, Montauk, New York



Definitely the go-to summer spot if you’re looking for a sophisticated day party.

290 Old Montauk Hwy, Montauk, New York

Best Brunch


The Topping Rose

We definitely did not just come here for the insta pictures – or did we?

1 Bridgehampton-Sag Harbor Turnpike, Bridgehampton, NY

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