Round Hill 12.24

Tropical Traditions: A Home Away from Home

There is something surreal about trading snowflakes for sea salt (or Charleston’s mild winter), but this past Christmas, our family did exactly that. We spent the 2024 Christmas holiday at the iconic Round Hill Hotel & Villas in Montego Bay. Beyond the stunning views, Round Hill holds a piece of our family’s history. For Taylor, this isn’t just a vacation spot; it’s where he grew up. He’s been coming here since he was a toddler, and the Jamaican community at Round Hill—many of whom have been there for decades—is truly his second family. It’s the place where we celebrated one of our biggest milestones, getting engaged in the hilltop garden on New Year’s Eve in 2018. Over the years, we’ve loved sharing this "hidden gem" with our closest friends, but this Christmas felt particularly full. For the first time, we brought the entire legacy together: my parents, our kids, and the familiar faces at the villa who have known Taylor since he was the age our children are now. Seeing our kids run through the same gardens their dad did thirty years ago made this trip more than just a holiday—it felt like a homecoming.

The Aesthetic: Ralph Lauren Meets the Caribbean

As someone who spends my days thinking about interior design, Round Hill is a dream. The resort feels like a curated time capsule of 1950s glamour. We stayed in Cottage 23, where the rooms—designed by Taylor’s Aunt—feature crisp white linens, dark mahogany four-poster beds, and classic checkered floors.

Holiday Magic, Island Style

With the kids being 5 and 3 at the time, the Pineapple Kids Club was a lifesaver. Meanwhile, we managed to sneak in some time at the spa and a few rounds of tennis. Our daily ritual of Afternoon Tea in the cocktail lounge—a nod to the resort’s storied history.

Leaving Round Hill felt like leaving a family home. Between the warm "welcome home" from the staff and the slow, rhythmic pace of the island, it was the perfect reset before heading back to the hustle of Charleston.

If you’re looking for a holiday that prioritizes connection over commercialism, put Round Hill on your 2027 list.