Travel Guide: The Hamptons

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I was so lucky to spend a bit of time in the Hamptons this summer. I visited family and friends who spend their summers there as an escape from New York City. Perhaps my favorite part of the vacation was driving along Montauk Highway and stopping off in each town. They all have different things to offer.

Rhyme & Reason's Hamptons Travel Guide

I stayed in Sag Harbor, which, I admit, is my favorite town in the Hamptons. It is the quintessential American harbor town. The main drag, properly named Main Street, is lined with light posts adorned with hanging flower baskets and American flags. At the end of Main Street, your eyes grow wide as you see all the boats docked in the beautiful harbor.


In Sag Harbor, be sure to eat at Dockside Bar & Grill. The restaurant sits across from the water, boasts a view of Billy Joel’s house, and serves an incredible lobster roll. For Italian food and delicious rose, head over to the newly opened Doppio (the mushroom pappardelle is heavenly). Be sure to walk off your meals along Main Street by popping your head into Fishers Home Furnishings for nautical interior decor and Life’style boutique for lines including Rag & Bone and Sundry. Finally, indulge your sweet tooth at Buddha Berry Frozen Yogurt or Big Olaf Ice Cream. I went to both! You want more food recommendations!? Stop by Harlow East, LT Burger, Sen, Pepalajefa, and The Juicy Naam.


The trip also brought window shopping in East Hampton (hello Jack Rogers, Lilly Pulitzer, The Monogram Shop, Ralph Lauren, Zimmermann, and Calypso) as well as stopping at farm stands in Amagansett. I tried a Physique 57 barre class in Bridgehampton and ventured all the way up to the easternmost most point of the Hamptons to climb the historic Montauk Point Lighthouse.


Don’t forget to pop into the Serena and Lily store (one of only two stores)… it is fabulous!


If you are going to the Hamptons soon (it’s not too late to book Labor Day!), here is a list of things to do, restaurants to go to, stores to shop at, and places to stay:


  • Eat:
    • Calm Bar: for roadside seafood consisting of fried clams, lobster rolls, and clam chowder
    • Amagansett Farmer’s Market: for local produce and baked goods (everyday except Tuesday and Wednesday)
    • The Lobster Roll: for “the best lobster roll in the Hamptons”


  • Go out:

East Hampton:

  • Eat:
    • Bay Kitchen Bar: for a to die for raw bar and views of the water at sunset
    • Mary’s Marvelous: for sandwiches and snacks (perfect for picking up on the way to Main Beach!)
    • Nick & Toni’s: for local seafood and a Mediterranean/Italian inspired menu
  • Shop:
    • Shop along the two main shopping streets – Main Street and Newtown Lane


Enjoy the longest post ever and the Hamptons!

Rhyme & Reason's Hamptons Travel Guide

My mom and me not wanting to leave…

…Be sure to follow me on Instagram for all travel photos!

Rhyme & Reason's Hamptons Travel Guide

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