There are no nonstop flights to St. Barth’s, which means the journey itself becomes part of the adventure. Eric and I began with a trusty United Airlines flight to St. Maarten before boarding a tiny island hopper operated by Winair Airlines for the short final leg into St. Barthélemy. The plane felt a bit coffin-like, and I joked that I was relieved the airline wasn’t called “Lose-air,” because that might have set the wrong tone for the trip. Instead, the moment we touched down, the island began to work its quiet magic.

Landing in St. Barth’s is always an experience. My heart still skips a beat as the plane makes its steep descent over La Tourmente, but the cure comes quickly the moment you step out into the warm, humid air and feel the island quietly welcome you in. 

The Best Kind of Travel Companion

Eric and I have traveled with Matthew and Phillip before, and they are simply the best kind of travel companions. From time spent at their homes in the Hamptons and Bucks County to two unforgettable visits to our home in Tucson—where we explored the Southwest desert, ventured into Northern Arizona, and even made our way down into the Grand Canyon with my best friend Rick—we knew this trip would become another wonderful chapter together. 

Matthew and Phillip had stayed in our St. Barth’s rental before, and they absolutely lit up whenever they talked about it—a secluded compound perched on the edge of a cliff overlooking the water in a quiet alcove. Their enthusiasm only made me more eager to see it for myself.

A Week in Our Caribbean Sanctuary

When we arrived, it felt like discovering our own private Caribbean hideaway. Two charming bungalows with mint-green shutters and cool, air-conditioned bedrooms were connected by winding garden paths and open views of the sea. At the center sat an open-air kitchen, dining area, bathroom, and living space where the breeze moved freely and evenings stretched gently beneath the trees and shrubs lining the hillside.

For the next week it became our home base and gathering place—an oasis we returned to after days spent hiking, running, and exploring the island’s beaches. And while the island encourages you to forget about the outside world, a few of us still had the occasional responsibility to tend to. So, between swims and sunset cocktails, there were a handful of Zoom calls taken and PowerPoint presentations written—conducted, somewhat improbably, from this breezy perch by the sea. Somehow even work feels a little lighter when your office happens to overlook the Caribbean.

Originally, I imagined we would cook most evenings—grilling fresh fish, lingering over candlelit dinners, and opening bottles of wine as the sun slipped into the sea.

But St. Barth’s had other plans.

That’s not to say we didn’t stock up on essentials at the Super U market—nuts, wine, fruit and vegetables, cheese, croissants, and good coffee to ease us into the mornings. Yet when it came to the serious business of eating, we almost always found ourselves out on the town, exploring the island’s extraordinary restaurants instead.

A Culinary Playground in the Caribbean

The culinary scene on the island is one of its great surprises. Though St. Barth’s itself is small, its restaurants rival those of major European cities, blending the elegance of French cuisine with the bright, sun-washed flavors of the Caribbean. Dining there often feels like a tropical extension of the French Riviera—Michelin-trained chefs cooking with impeccable technique while the sea glimmers just beyond the table.

Phillip and Matthew wisely convinced us to lean into it.

The boys took the reins, securing reservations across the island and sketching out our daily rhythm of beaches, hikes, and meals. Matt may have been responsible for some of the more ambitious running and hiking plans, but once we were all together every outing became a shared adventure.

Restaurants on St. Barth’s are as memorable as the food itself. Some sit in lush tropical gardens or perch above Gustavia Harbor, while others spill directly onto beaches where the soundtrack is the gentle wash of waves. Menus range from elegant tasting dinners to long, sun-drenched lunches at beach clubs where rosé flows freely and the afternoon slowly dissolves into sunset. And while the prices occasionally made us glance twice at the menu—this is St. Barth’s, after all—the beauty of the settings and the quality of the food somehow made it, all feel like part of the experience.

An Evening at Tamarin

Our first evening set the tone for the week. We were joined by Alex Damalas and his partner, Gabriele Tonini—fellow New Yorkers who, like us, appreciate how easily St. Barth’s allows East Coasters to slip away from winter.

The six of us gathered in the lush garden at Tamarin, where Chef Jean-Claude Dufour’s kitchen truly lives up to what he calls the “Spirit of Culinary Research.” Under the soft glow of lights strung through the trees, plates arrived in perfect rhythm: crisp duck egg rolls, deeply satisfying mushroom and gambas ravioli, and lobster medallions alongside delicate sole that felt almost celebratory. The attentive staff guided us through a thoughtful wine list that elevated every course. 

It was one of those evenings when time slows down, conversation flows easily, and good friends gathered around a table remind you how special travel can be. The only guest who seemed equally delighted by the setting was the island’s mosquito population, who apparently decided Eric was the evening’s special. He left dinner with a constellation of bites to remember the night by—his own little souvenir from Tamarin’s Garden.

The Dinner That Set the Tone for the Week

We were lucky enough to see Alex and Gabriele again later in the week for another memorable dinner—this time at Bonito—just one of several extraordinary meals that made the island feel like a true culinary pilgrimage. If you are so included for after dinner sweets, I’d recommend the Passion Fruit Soufflé, one of the most talked-about desserts on the island. Light, airy, and tangy, it reflects the tropical fruit flavors common in St. Barth’s dining. We actually ordered two, for safe measure.

Over the course of the trip, we savored everything from refined dining at La Case at Cheval Blanc, Esprit, and Eden Rock to relaxed island favorites like Le Select, Shellona, and Manapany. We also enjoyed cocktails overlooking the water at Rosewood Le Guanahani, grabbing a seat at Bar Mélange or at the Beach House along the shore.

It was there that we connected with a couple of Phillip and Matt’s new friends—people they had only recently met through mutual friends who live in the boys’ apartment building in the city. Among them was the gorgeous Aurélie Garreau, proprietor of worldwidebutler.com, which offers exclusive butler services in Saint-Barthélemy, Saint-Tropez, and beyond. Aurélie is not just a professional in the art of hospitality—she’s a partner in transforming every moment into an unforgettable experience. She was joined by her handsome boyfriend, Nicolas Parlier, one of the most accomplished athletes in modern wind-powered board sports. A multiple-time world champion in kite foil racing, Parlier is widely regarded as one of the fastest riders in the sport

We also made our way to a humble hamburger spot—considerably less expensive than the half-dozen other eateries we had been frequenting, yet it brought us just as much joy. After long hikes and sun-soaked afternoons, their gloriously calorie-laden lunches felt entirely justified. The menu ran the gamut from juicy hamburgers and hearty burritos to freshly made ice-cream shakes that tasted like vacation in a glass.

In fact, we enjoyed it so much that we found ourselves going back a second time—strictly for research purposes, of course. 

Some Memories Are Best Shared with Friends

Yet the real highlights of the week were not just the meals—extraordinary as they were. They were the days spent with friends: hiking along sun-washed trails, running the island’s winding roads, and swimming in water so blue it hardly seemed real.

One of the most meaningful moments for Eric and me came when we returned to Gouverneur Beach, a place we had not visited in more than twenty years.
As we rounded the corner and began the descent toward the beach, parking proved scarce. Poor Matthew had to carefully back the car up the hill to find a spot along the road. As we stepped out and looked toward the water, the floodgates of memory opened.

The last time we stood on that stretch of sand, we had been guests of Francis Goelet—a noted philanthropist and music patron whose family once owned the parcel of land at the bottom of the hill. Back then his private home sat quietly behind the trees, and the beach felt like a hidden world.

Standing there again decades later with our friends, the memories felt wonderfully close.

We walked the full length of the beach, slipped into the warm ocean for a long swim, and stretched out under the Caribbean sun. At one point, two baby goats wandered out from the foliage and meandered around us, and several full-sized sea turtles slowly made their way up the sand, passing between our towels as if we were simply part of the landscape. It was one of those rare, perfect afternoons when time seemed to pause for a moment.

Eric and I finally confessed to our travel companions that Gouverneur also held another bit of personal history for us. More than twenty years ago, it was the first beach where we truly embraced the freedom of the island and left our worries—and a few articles of clothing—behind. 

Somewhere in our archives sits a playful over-the-shoulder photograph from that moment. For fun, we recreated it two decades later for posterity. That particular photo will remain safely in the “three-martini stories” category—best enjoyed privately among friends and good memories.

And perhaps that is the real gift of travel. Places change. Time moves forward. But when you return with people you love, the past and present have a beautiful way of meeting each other again.

Another Island, Another Adventure

After Matthew and Phillip departed, Eric and I enjoyed one final quiet lunch at Eden Rock before continuing our journey to St. Thomas for a few days. Neither of us had spent meaningful time on the island before, and curiosity got the better of us. We wanted to see the beaches, explore a few hiking trails, and, of course, sample the local cuisine.

St. Thomas greeted us with that unmistakable Caribbean rhythm—warm breezes, turquoise water, and hills that seem to drop straight into the sea.

We spent our days wandering along powdery beaches, hiking winding trails that revealed sweeping views of neighboring islands, and enjoying relaxed island meals filled with fresh seafood and local flavor. 

There’s no real need to mention the hotel we chose, as there’s nothing to be gained from sharing negative news. Let’s just say that although we booked through American Express and expected a certain standard from the collection it belonged to, the initial experience didn’t quite live up to those expectations.

Suffice it to say that by the time we moved to our second room—the one without the stained and torn bedspread—things improved considerably, and we were finally able to settle into the island rhythm.

Fortunately, the beauty of St. Thomas quickly took center stage. Between the beaches, the hikes, and the flavors of the island, the days unfolded exactly as we had hoped—slow, sun-soaked, and full of discovery.

The food was delicious everywhere we went, and every person who served us made us feel genuinely at home. The service felt first class in that warm, easy island way—attentive without ever feeling formal. And for those who enjoy a bit of sparkle in their glass, we were delighted to discover that Whispering Angel rosé was about $50 a bottle on St. Thomas, compared with the nearly $200 we had grown accustomed to seeing in St. Barth’s. I suppose that’s where the phrase “Bring Your Own Wine” might come from—because once you’ve seen the St. Barth’s wine list, you start thinking about creative solutions.

A Day Trip to St. John

Our favorite hike during the second part of our holiday took us to nearby St. John.

The fastest and most popular way to get there from St. Thomas is by passenger ferry from Red Hook, a short fifteen-to-twenty-minute ride that arrives in Cruz Bay and runs regularly throughout the day. 

Once we stepped off the boat, we wandered into the Friends of the Park Store located inside the Virgin Islands National Park Visitor Center.

The small shop offers a thoughtful selection of souvenirs and mementos that directly support the park’s conservation efforts. It’s a natural stop for visitors looking for educational materials, locally inspired gifts, and official park merchandise.

More importantly, it sits just steps away from the network of hiking trails that weave through the park. 

From there we set out on the Lind Point Trail, a roughly one-mile tropical path that winds through lush vegetation above the sea. The hike takes about twenty to thirty minutes and is relatively easy, though parts of the terrain can be rocky, steep, or muddy depending on recent rain. 

At the end of the trail the reward reveals itself: Honeymoon Beach, where the turquoise water seems to glow against the pale sand.

Standing there, looking out across the bay, it felt like the perfect exhale at the end of a wonderful journey.

The Real Luxury

Standing there on Honeymoon Beach, looking out across the quiet bay, it felt like the perfect exhale at the end of a wonderful journey. 

Travel has a way of reminding you what matters most. Yes, the islands were beautiful. The meals were extraordinary. The hikes, the beaches, and the turquoise water delivered everything we hoped for when we first boarded that tiny plane bound for St. Barth’s.

But the truth is, the real highlights of the trip were never just the places themselves.

They were the moments shared along the way—the laughter over long dinners, the miles of winding roads we ran together, the quiet swims in irrepressibly blue water, and the stories that resurfaced when we returned to places that had quietly held pieces of our past.

Travel changes as the years pass. Destinations evolve. Restaurants come and go. Hotels improve—or occasionally require a room change.  But the magic of a journey endures when you experience it with the right people.  And perhaps that is the greatest luxury of all—not the view from a cliffside bungalow or a table at a remarkable restaurant with a flambé dessert, but the privilege of sharing those moments with friends and loved ones who make every mile of the journey meaningful.  Because in the end, the places we visit may remain behind us—but the memories we create together are the ones we carry home.

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