From the misbehaving high school kids of Gossip Girl, to the ambitious career women of Sex And The City, to the scheming families of Revenge, The Hamptons has proven to be an idyllic location to fulfill all these characters’ whims and desires, however extravagant or outrageous.

Away from the boundless energy of The Big Apple, it’s actually a string of towns and hamlets located on New York’s Long Island area – and has been known as one of America’s foremost seaside resorts and historic summer colonies. This is because for the crème de la crème of Manhattan society, New York City is a mere weekday launchpad, enabling them to jet off for weekends of exquisite leisure.

But how exactly do these VIP travelers wine, dine, and party in this secluded corner of New York? Curious to find out for myself, I decided to embark on a little weekend getaway of my own. #JuanderWithUs on my latest travel blog, as I explore the grand estates, charming beaches, and fabulous restaurants of the Hamptons.

Like other city residents, I first travelled to the Hamptons on a Saturday, making my way from the busy streets of New York, to find a calmer respite in its beautifully manicured coastal neighborhoods. Goodbye for now, NYC!

I soon headed to a town called East Hampton, which recently made headlines for being home to one of the most expensive pieces of property in America, up for sale for a whopping US$ 175 million. If this isn’t outrageous enough for you, I don’t know what is. Still, I arrived to what is a much quainter, yet equally stunning home up in the neighborhood. Designed in a classic American style, it’s a place that radiates plenty of charm and serenity – at first sight, I was so ready to rest and relax right away.

It felt great that I could just unpack my bags and explore what this country home has to offer.

All this R&R is making me hungry. Luckily, lunchtime came as fast as a New York subway. For my first Hamptons meal, I went to Lulu Kitchen and Bar on Sag Harbor. The menu here centers on wood-burning cuisine, with everything from their mussels, cowboy rib eyes, and even their salads possessing a distinct smoky taste.

Now that I’m filled up, I’m ready to wander along some more! My first stop – the comfort of my own garden.

It’s like having a little piece of your own rustic paradise.

Exploring the interiors was also an inspiring journey in itself. Walking around, I noticed a mix of classic and historical elements, drawing on the styles and trends of the 1600s – way back when America was still under the British Empire.

Upstairs, the view was even more charming – as if I jumped back in time to a much simpler era. From the warm lighting, to the floral wallpaper, and the abundant use of aged wood, I found it to be a truly charming home worth vacationing in.

Sundown came soon enough. Wanting a little more food, I took a trip to the nearby 1770 House Restaurant and Bar – now considered a gastronomic institution among the locals. Open for more than 250 years, its heritage interiors are contrasted by a contemporary American menu: I highly recommend their blue cheese salad and Himalayan salt and potato-covered New York strip. Both are dishes just about anyone would love.

As night completely fell, I decided to go back home. Arriving, I saw a particularly beautiful sight – the pool was fully illuminated, and all the lights were on amid the autumn darkness. Looks like the perfect place to luxuriate some more! And luxuriate I did.

Still, all became a little spookier once a few lamps were turned off. Thankfully, there weren’t any spirits to vacation with me!

After all this, I soon went to bed – thinking of all the great things left to see in this fabulous corner of New York state. The beach awaits.

As the next day came, I was eager to wake up early to simmer in the cool morning breeze. Walking along the smooth coastline was just wonderful. One could feel a sense of serenity as you see the crashing of the waves, alongside the magnificent views of the beautiful houses nearby.

 

As the beach was conveniently located near home, I walked back to the yard to see an even more pleasant sight. The sun was shining brightly – giving the home and its surrounding greenery a golden glow.

With such a beautiful day ahead, I hurried up and got dressed right before I visited my next stop – the town of Sag Harbor.

In this village, there is a laidback aura – less of the overt glamour of towns opposite the area. Rows of American flags snap smoothly in the wind, its residents proudly displaying their heritage. On the other hand, artisans and designers also take pride in their stunning creations, which range from wicker baskets to jewelry, to even furniture. According to the locals, Sag Harbor is a place where everyone can simply let loose. No need to feel conscious about who you are or how much you have. How refreshing.

Another of The Hamptons’ iconic sights are its shingled windmills, which add a uniquely rural charm to its small towns. With their abundance, you’d sometimes feel that you’re in the Dutch countryside rather than in America.

I’ve also come to love the autumns here in The Hamptons. During my stay (which was on September), the place was in that sweet spot between summer and fall, making for a picturesque contrast between the greens and yellows of the hills, and the browns and reds of the trees. Magical!

The next stop on my journey was another Hamptons icon: the Gurney’s Montauk Resort and Seawater Spa. Located on one of the most pristine stretches of oceanfront real estate on Long Island, it has become one of the most coveted health and leisure venues in all of North America. Where else can you book a healing treatment one hour, and sip on your martini in an ocean-fed seawater pool the next? Best of all, its very own Beach Club offers unrivalled views of the Atlantic, as the only direct beachfront food and beverage experience in the area.

From the beach, I then came across another Hamptons “gem”, the famous Tate’s Bake Shop. Fans have declared its chocolate chip cookies to be “the best ever made”, given that they are sold in some of the most prominent gourmet shops across the country. Still, the charming cottage churns out other sweet treats, including cakes, scones, bread puddings, and pies. With such an irresistible selection, I just had to buy some.

While I didn’t want to leave the bakeshop just yet, it was getting dark, and I felt the urge to get a little rest. Sitting on a bench by the East Hampton Main Beach proved to be the best option.

I then just needed a place to kick my feet up while I enjoyed the remainder of my stay. Some Sunday night television in the living room would do the trick, just before bedtime.

And in what seemed like a quick snap of a finger – it was already Monday. There was still a little time left to stroll around, so I went ahead for one last look at the beach, and the homes of my (temporary) neighbors. I’ll definitely be back for another weekend.

Sadly, my time here at the Hamptons had to be cut short. More things had to wait back at The Big Apple. However, my short but sweet stay in New York’s beach paradise was filled with prominent and even a few unexpected gems.

Beyond its glamorous façade is a place possessing a well-preserved heritage, something that is seen in its grand homes, artisan crafts, and its wonderful restaurants. My verdict: The Hamptons are a must visit for everyone with a taste for the finer and deeper things in life.

Want your own Hamptons weekend escapade? Our #WorldJuanderer travel specialists can help you craft something truly unforgettable – inquire with us now. #WithYouWhileYoureOutThere