Rediscovering the Magic of Grand Cayman

Fifteen years of family traditions, a twelve-year absence, and what I found when I finally went back.

Seven Mile Beach. Photograph courtesy of The Westin Grand Cayman Seven Mile Beach Resort & Spa.

I still remember sitting on the living room floor by the Christmas tree, holding a mysterious envelope. My brother and I were puzzled when a brochure for a property in Grand Cayman tumbled out. We knew our parents had traveled there a few weeks earlier — but we had no idea they’d just bought a timeshare. That Christmas morning began a fifteen-year love affair with the island, the backdrop for my family’s most cherished traditions.

Six months later, I stepped off the plane into that familiar, brilliant Cayman sunshine. Back then the airport was essentially open-air; I still remember the observation deck where we’d stand waiting for arrivals. I was quickly introduced to “Cayman Time” — the local rhythm that moved just a little slower than I was used to. My mother grabbed the rental car, and our week-long adventure began.

For the next fifteen years, the East End was our sanctuary. We rarely ventured into George Town or Seven Mile Beach. We learned that the grocery stores closed on Sundays, and after navigating the harrowing roundabouts just outside the airport, we’d cruise along the main road toward the quiet, far end of the island. My brother and I brought our fiancés; my grandmother joined us for a few trips; and eventually, we brought our own children. Those days were filled with sun, laughter, favorite restaurants, and the kind of long, lazy beach naps that defined my youth. But as life happens, the trips eventually stopped — and I found myself on an unplanned twelve-year hiatus from my favorite place.

Earlier this year, I finally had the chance to return. The island had changed, but it certainly didn’t disappoint. My father and brother are gone now, so my mother and I made the journey together. My first impression? Wow — this place has evolved. The plane door still opened into that glorious sunshine, but the open-air airport I remembered was gone, replaced by a sleek, air-conditioned facility with modern security. As our taxi drove toward Seven Mile Beach, I couldn’t believe the transformation — the traffic, the sophisticated shopping centers, the proliferation of roundabouts.

Yet as we chatted with our taxi driver, the memories came rushing back — centered on the most important part of the island: the people. Their warmth remains undiminished. They have a deep, palpable love for their home, and they’re as eager as ever to welcome visitors and share their culture.

The warmth continued at our hotel. Check-in might have been a little more relaxed than what we’re used to in the U.S., but it was noticeably more efficient than the “Cayman Time” of my youth. Across our stay at two different resorts, we were greeted with the same genuine hospitality that defined my childhood memories.

The evolved Seven Mile Beach coastline. Photograph courtesy of Grand Cayman Marriott Resort.

Where I stayed

The Grand Cayman Marriott Resort. My journey began here — a hotel that holds a special place in my family’s history, since it was the reason my parents discovered our timeshare in the first place. My father had famously misread a map, convinced he needed a “Marriott” on the other side of the island (spoiler: it didn’t exist — just a property with a similar name). While the years have shifted the beach in front of the hotel due to storm activity, the soul of the resort remains. The service and culinary offerings are as stellar as ever, and it’s still home to Red Sail Sports, a legendary island fixture. If you’re looking to get out on the water — windsurfing, snorkeling, or world-class scuba — they remain the gold standard.

The Grand Cayman Marriott Resort. Photograph courtesy of Grand Cayman Marriott Resort.

The Westin Grand Cayman Seven Mile Beach Resort & Spa. For the second half of my trip, I moved here — a true full-service resort, offering everything from casual coffee shops and fresh sushi to refined fine dining. The beachfront is spectacular; it’s my top recommendation if your goal is to spend your days with your toes firmly in the sand. One highlight was an intimate dinner at the resort’s signature restaurant, Beach House — the perfect setting for a special evening under the stars.

An evening at Beach House. Photograph courtesy of The Westin Grand Cayman Seven Mile Beach Resort & Spa.

Some landmarks of my youth have faded — the beloved Lighthouse restaurant, the quiet roads of the East End, the raw beauty of the Blow Holes. But as I explored, I realized the modern Grand Cayman has held onto the charm of the island I grew up with. It has evolved, matured, and polished its offerings — but the heart of the island remains unchanged. As it turns out, I love this new chapter just as much as the first.

Dreaming of your own island chapter?

Tell me a little about your travelers and your hopes, and I’ll personally be in touch.