From Fantasy to Reality: Experiencing the Hamptons for the First Time
The Hamptons have always been a dream, that far-off place you hear about but never quite touch — like a child imagining the wonder of Disney World, just beyond reach. My fascination began years ago, curled up in my college dorm, lost in the world of Revenge. Emily Thorne, with her carefully laid plans, and Victoria Grayson, who radiated icy elegance, became my personal tour guides to the Hamptons' world of wealth and secrets. Funny thing is, now I often see Victoria Grayson — or rather, her real-life counterpart — in a coffee shop in Santa Monica every Friday. She still has that soul-piercing gaze, the kind that makes you feel like she could unravel your life with just a glance. It’s almost like the Hamptons followed me across the country.
And then there was Gossip Girl. High school, college—those years were shaped by my obsession with the Upper East Side, trying to decipher the allure of New York City and the Hamptons. Chuck Bass was my favorite character on the show, a man whose dark charm and complexity I found myself channeling more often than I’d like to admit. His father, Bartholomew “Bart” Bass, was a billionaire at the helm of Bass Industries, a titan who cast a long shadow over Chuck's life. Yet, it was Bart’s wife, the captivating Lily van der Woodsen, who truly embodied the elegance of that world. She possessed a grace, beauty, and class like no other, effortlessly commanding any room she entered, a perfect complement to the world of power and privilege that surrounded her. Revenge and Gossip Girl were windows into another world—a world of privilege, power, and intrigue. Both shows spun tales of wealth, luxury, and drama, setting the stage for my fascination. To finally experience the Hamptons in real life... it felt like stepping into another dimension entirely, as if I had crossed the threshold from dream to reality, with all its whispers of secrets and opulence.
“My entry into this exclusive world came via the Supper Club, a private members’ club. In under a year, I’d dined at top-tier restaurants, explored Kyoto and Tokyo, and now this—crossing another dream off the list with a trip to the Hamptons. Supper Club had introduced me to an eclectic, fascinating crowd—plastic surgeons, financiers, writers, Ivy Leaguers—all bonded by a love for impeccably curated dinners. And when it came to planning the Hamptons trip, they left no stone unturned.”
And then there was Mad Men. That show was my anchor. Set in the very world I would soon navigate myself—advertising executives, tailored suits, and sharp conversations on Madison Avenue—it was more than a show. It was a glimpse of what my life could be, the path I now find myself on. Don Draper was the character I admired most, a figure who embodied the complexities of ambition, reinvention, and the relentless pursuit of perfection. He was the man who could sell an idea with a single, confident glance, a visionary behind the polished façade of 1960s Madison Avenue. Beneath the sharp suits and carefully crafted image, there was a storm—one that made him unpredictable, enigmatic, and utterly compelling. His charm, his flaws, his ability to create something from nothing—it was all part of the mystique that made him more than just a character, but a force of nature I couldn't help but be drawn to. So when the opportunity to visit the Hamptons arose, I knew I couldn’t pass it up. The suits, the sophistication, the marketing genius I once admired now felt like echoes of my own career.
My entry into this exclusive world came via the Supper Club, a private members’ club. In under a year, I’d dined at top-tier restaurants, explored Kyoto and Tokyo, and now this—crossing another dream off the list with a trip to the Hamptons. Supper Club had introduced me to an eclectic, fascinating crowd—plastic surgeons, financiers, writers, Ivy Leaguers—all bonded by a love for impeccably curated dinners. And when it came to planning the Hamptons trip, they left no stone unturned.
Finally, I was about to experience it firsthand. The Hamptons.
It started in New York City with a prelude to the weekend: dinner at Don Angie in the West Village, a restaurant so exclusive it feels like it exists on another plane. Their Italian menu was divine—sourdough pasta, stuffed flatbread, and cocktails that pushed the boundaries of creativity. And the lasagna—oh, that lasagna. Let’s just say it’s worth every rave review.
The next morning, it was time to head to the Hamptons. Most took a helicopter via Blade, while others drove or caught the Hampton Jitney. I opted for the Hampton Jitney, eager to soak in more of the city’s charm, but I missed the first bus by a breath. The silver lining? The pickup spot was at a steakhouse, so I treated myself to a branzino and a couple of glasses of Sauvignon Blanc while waiting for the next bus. When the next Hampton Jitney arrived, I was feeling the kind of relaxed you can only achieve through a perfect mix of good food, wine, and anticipation. The three-hour ride took us through Bridgehampton, East Hampton, Amagansett, and Montauk, with my stop conveniently in front of my first hotel for the night, the cozy Huntting Inn, where luxury met small-town charm.
From the moment I stepped off the Hampton Jitney, it was like walking into the pages of a Ralph Lauren catalog. The surrounding shops—Chanel, Polo Ralph Lauren, Prada, and J.Crew—were a delightful surprise, tucked away in quaint storefronts.
“That evening, cocktails awaited us at the Maidstone Hotel in East Hampton, where I’d be staying the next two nights. It was like stepping into a Gatsby novel—cocktails flowed, appetizers were divine, and the company was even better. Dinner was a feast of Wagyu steak, Dover sole, cacio e pepe, and more, each dish crafted with meticulous care. Seated among Miami elites, NYC socialites, and even a few prominent political figures (yes, I shared a bathroom line with a former U.S. Speaker of the House), I felt as though I’d been let into a secret, elegant club. Casual, right? I ended up chatting with him and his security detail by the bathroom. The night? Spectacular.”
That evening, cocktails awaited us at the Maidstone Hotel in East Hampton, where I’d be staying the next two nights. It was like stepping into a Gatsby novel—cocktails flowed, appetizers were divine, and the company was even better. Dinner was a feast of Wagyu steak, Dover sole, cacio e pepe, and more, each dish crafted with meticulous care. Seated among Miami elites, NYC socialites, and even a few prominent political figures (yes, I shared a bathroom line with a former U.S. Speaker of the House), I felt as though I’d been let into a secret, elegant club. Casual, right? I ended up chatting with him and his security detail by the bathroom. The night? Spectacular.
The next morning, I checked into the Maidstone Hotel, feeling a little worse for wear from the previous night’s indulgence. While waiting for my room, I perched at the bar, reflecting on the surrealness of it all. Later that afternoon, we gathered at our new friend Robb’s home for a reggae-filled backyard party. Homemade pizza, grilled chicken, cocktails—it was one of those perfect summer days, the music and laughter mingling as the sun began to set. By evening, we found ourselves at Murf’s in Sag Harbor, a local dive where we spent hours playing bar games, laughing, and soaking up the unpretentious charm of the Hamptons.
The next day’s brunch at Le Bilboquet in Sag Harbor felt like the perfect curtain call to an unforgettable weekend—a ritual I now couldn’t imagine skipping. Sunlight glistened off the harbor’s boats, while bees flitted around us like tiny, unexpected guests at the table. Lobster and steak graced the table, each bite a reminder of the Hamptons’ indulgent charm, as if the weekend wasn’t quite ready to let us go.
Later, as if the Hamptons wasn’t quite done with us, some of us made our way to Amagansett for a round of bar hopping. In true Hamptons fashion, what began as casual drinks quickly escalated into arm-wrestling with locals, and before I knew it, we were swaying to reggaeton in a seaside dive. The unexpected presence of reggae in the Hamptons was a revelation, a rhythm that pulsed through the weekend, blending with the waves in a way that felt perfectly, and delightfully, out of place.
As I reflect on the weekend, I can say, without hesitation, that it was one of the most enchanting experiences of my life. The meals, so decadent they felt like art; the homes, standing like monuments to a world of quiet luxury; the people, effortlessly elegant in every way—it was as though I had stepped into a scene from a Ralph Lauren ad, where time itself seemed to slow down under the flutter of American flags, rippling against the backdrop of glittering estates.
What had once been a distant, wistful dream is now a vibrant, undeniable reality, richer and more luxurious than I ever could have imagined. The Hamptons, with all its breathtaking splendor and undeniable charm, was no longer just a fantasy. The dream had come to life, more beautiful, more magical than I ever dared to hope. It was a moment where everything aligned—where dreams transformed into something real, and let me tell you, it was more than worth the wait.
Follow me on Instagram (@mr.antoniodspears) to catch all the photo threads from my Hamptons getaway. Don’t miss the Hamptons highlight reel!
