A First-Time Visit to Long Island & The Hamptons

A first-time visit to Long Island and the Hamptons in June including a weekend at the Manhattan Waldorf Astoria, a drive through the Hamptons to the Lighthouse at the tip of Montauk, followed by another scenic drive through the northeastern wine country to Greenport.

Montauk lighthouse hamptons long island travel

I visited Long Island and the Hamptons in June for the first time and also managed to squeeze in a weekend at the Waldorf Astoria in Manhattan. The standout moment of this trip though was the drive through the Hamptons to the Lighthouse at the tip of Montauk, followed by another scenic drive through the northeastern wine country to Greenport.

Our stay in Long Island was a strange mish-mash of work-related activities and for me, hanging about the Melville Marriott Hotel enjoying the indoor heated pool and the balcony bar in the afternoon.

One night, after some Italian food with a couple of co-workers/friends, we found our not-so-deeply-buried inner child at the nearby Dave and Buster’s—the more tickets we won, the more martinis we had.

A Weekend at the Waldorf-Astoria

Waldorf astoria new york
“[On looking at the Waldorf on Park Avenue] I suddenly realized that I was seeing a dream, a wild, all but impossible dream, fulfilled – and that can’t help but fill a man with awe.” | Conrad Hilton

Staying at the Waldorf Astoria was a history lesson. Wandering about the lobby exhibits revealed the various celebrities and political figures who had stayed there, and the layers of time and events that had occurred during the hotel’s storied lifespan. We were given a corner room, large and open. 

The Tony Awards were taking place on Sunday, and we briefly considered getting a ticket, but we opted for letting the city itself entertain us. 

I did have the best cheesecake of my life thus far that weekend, and I can’t even remember the whole-in-the-wall’s name. But isn’t that always the way? I wasn’t even hungry, and I rarely eat desserts, but every last morsel of that thick, golden, creamy, crustless cheesecake was scraped from the plate. 

We randomly got tickets for Once: A New Musical at the TKTS booth in Times Square, and scored 2nd-row center seats. A richly entertaining show with hauntingly beautiful music and an intriguing storyline. 

The next time we’re in New York and find ourselves near the Waldorf, we plan on ducking into the Peacock Alley lobby bar where, hopefully, the stoic yet charming bartender will still be there, ready to slide me more samples of any cocktails he overhears me say sound delicious. 

The Gold Coast: Long Island and the Hamptons

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Driving through the Gold Coast and along the coastal highways of Long Island and the Hamptons was really the best way to experience the diversity of the people, lifestyles, and architecture of the island. 

With no particular sights to see, we drove towards the Montauk Lighthouse, and other than that, the open road and our inclinations were our only guides. 

Long island travel road taken to

The weather went from a warm, moist thickness to transparent coolness when the sun went down behind the misty clouds, where water and sky melded into one pastel hue. 

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On our way back from the Montauk Lighthouse, we suddenly realized how hungry we had become and looked up restaurants nearby. 

While there weren’t that many options to choose from considering we were fairly far afield at that point, one restaurant caught our eye called Navy Beach

Long island travel road taken to
Navy Beach

But, to get there took driving along deserted white, sandy shale roads that slowly zigzagged down to the water’s edge. Then, there it was. 

A low building with dark rafters, fresh seafood, the sounds of lapping water, and ice-cold Moscow Mules. A quiet, low-key place where everyone slowly went about their business with zero traces of the frenzied Manhattan vibe.

I remember talking to a local girl from Montauk who said that she had lived in Long Island all her life and had only visited Manhattan two maybe three times–primarily for field trips in school. 

At the time, I thought it was strange, but proximity doesn’t really mean anything, does it? 

Just because you live next door to a gym, park, or even one of the most exciting cities in the world doesn’t necessarily mean you visit them. 

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“How happy is the blameless vestal’s lot! The world forgetting, by the world forgot. Eternal sunshine of the spotless mind! Each pray’r accepted, and each wish resign’d” ― Alexander Pope, Eloisa to Abelard

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