Winter in the Hamptons

Last winter, in lieu of a trip to a warm beach, we decided to stay within driving distance and head to a different beach—Long Island. We got to see the beautiful coasts of the Sag Harbor and Montauk, which are just as enjoyable in the winter as over the summer. Here’s what we did:

Friday

Our hotel … We arrived in Bridgehampton late afternoon and headed straight to the hotel. We stayed at the beautiful Topping Rose House, which was built as a colonial home in 1842. The hotel touts itself as the only “full-service luxury hotel in the Hamptons,” offering a pool, gym, spa, and a Jean-Georges restaurant. We got two of the last rooms available, located in the main house. The hotel also has cottages, which are more modern and offer more privacy. I had no issues with my room, but given the hotel’s age, my parents noted that the floors are thin, and they were kept up at night by the noise of the people above them. Next time, we would stay in a cottage, or at least on the top floor.

Afternoon … We then headed into Sag Harbor, our favorite Hamptons town, for some pre-dinner shopping. Located on the northern side of Long Island, the town is full of charming shops. Definitely check out Sag Harbor Books, which my mother and I agree is one of our favorite bookshops ever! It is so cute, and they always have great suggestions. You’ll also find lovely home decor stores, clothing boutiques, and apothecary shops.

Dinner … We ate dinner in Sag Harbor at Lulu Kitchen & Bar, which was phenomenal. The restaurant itself is gorgeous, the menu is creative and delicious, and the overall atmosphere might best be defined as elevated and hip. Even the background music is specially curated by the restaurant’s DJ. I had the cauliflower steak, a bit of burrata and mac and cheese on the side, and a chocolate hazelnut tart for dessert. All were amazing. I would definitely come back.

Saturday

Breakfast … We had breakfast at the hotel, which was delicious. My French toast was decadent!

Morning … We then headed even farther east out to Montauk, located at the easternmost tip of Long Island. Even our drive out was pleasant. We passed through the towns of Wainscott, East Hampton, and Amangansett before driving through undeveloped land and beautiful nature.

Our first hike was in Shadmoor State Park, comprising 99 acres in Montauk with beautiful views overlooking the Atlantic Ocean.

We then continued east to Montauk Point State Park, where we walked along the water and out toward Montauk Point Light, a beautiful lighthouse located at the easternmost point of Long Island.

Lunch … For lunch, we decided to try Tillie’s at the famous Gurney’s Montauk. The food was solid, but our overall lunch (which we ate outside) was very nice.

Afternoon … On our way back, we stopped in East Hampton to explore the town, before heading back to Bridgehampton. If you’re looking for a treat, head to Pierre’s for some delicious baked goods!

Dinner … Dinner was at a wonderful Italian restaurant in East Hampton called Dopo La Spiaggia. The restaurant offered some wonderfully done classic Italian dishes, which we greatly enjoyed.

Sunday

Breakfast … We again enjoyed breakfast at our hotel.

Morning … Before driving home, we went for a walk on the beach in Cedar Point County Park. The views of the Long Island Sound were beautiful. We then headed into the town of Sag Harbor once more to see the pier and its famous windmill.

Lunch … Wanting to get back home before rush hour, we picked up sandwiches from Harbor Market and Kitchen for the road. This spot is one of our favorites for a quick, delicious bite.

That concludes our weekend in the Hamptons. Although known primarily as a summer destination, the Hamptons are uniquely wonderful in the winter. We got to enjoy the area’s adorable towns and trails without the crowds. For only a few hour drive, we felt like we got a true mini-vacation.

Stay tuned for more posts about everywhere from Colorado to Ecuador, coming soon!

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