When I enter the gates of Round Hill, there’s a big piece of my heart that smiles. That piece of me, or my heart, from that moment forward feels like a kid again. Not just any kid, but one who grew up in Jamaica and remembers only the very best of her Island home. Even if you hadn’t grown up on this gorgeous island, there’s that childhood memory that tugs at you and has so imbued the person you are today that you could never shake it. To say that Round Hill captures the essence of that wonderful childhood would be an understatement. To say that it embodies the perfection of my fondest memories of my island home would also not suffice. Experiencing this resort is like being given and all access pass to the most surreal Island fairytale one could imagine. Now, that all sounds like high praise and farcical talk until you actually experience a week (or two) at Round Hill. Full disclosure, I have stayed at Round Hill close to a dozen times and the fact that it doesn’t change is one of the major reasons that I, and many others, are loyal repeat guests.
As I said in the opening of this story, it really is like going home. Things at home are typically what we expect and as we remember them. Home is as comfortable and reliable as our fondest memories make the out to be. The place that we slip into as easily and comfortably as a familiar set of house-slippers. My normal home-away-from-home here at Round Hill Hotel and Villas is cottage 18, now under massive renovation. Knowing this, I could not pass on the opportunity to visit one of my favorite properties in Jamaica and one of my top five picks anywhere in the world, for that matter. I decided that a stay at the hotel component, known as the Pineapple House, was going to be my choice this time around. These accommodations are white-on-white with dark wood furnishings and just the right amount of splashes of blue. The stark white contrast of the room and it’s warm décor stand very little chance of holding one’s attention once the doors to the terrace or windows to the room are flung open, which they will be. What lies beneath these rooms, decorated by the famous designer, Ralph Lauren, is the expansive infinity-edge pool and the softly undulating, Caribbean Sea. The foliage surrounding the Pineapple House adds just enough tropical lushness to give sunbathers and hotel guests, the privacy one seeks at such an elegant establishment.
From its very beginnings, back in 1952
There was never any doubt as to the direction of this property. I wasn’t privy to this knowledge as a first-hand observer, but the grandparents were and they have told the tales of British and American celebrities, royalty, and the very affluent who vacationed at Round Hill. This was to be the hideaway of the rich and famous; the well-heeled who sought nothing but the very best. The youthful iron of a young resort, some 70 years ago, has been forged into the splendor that is Round Hill, today. Through its curated growth– all inside its 100-acre expanse, the resort’s mettle had to have been tested, but like any home, nurtured by family, which here happens to be the staff, it never lost sight of the core values and its long-standing reputation. Day in and day out, they welcomed guests and return guests by name. They learned little details, without ever having a checklist or notepad on hand. They genuinely cared, day after day. To quote Hemingway’s For Whom the Bell Tolls, “Today is only one day in all the days that will ever be. But what will happen in all the other days that ever come can depend on what you do today.” What the Round Hill family does, effortlessly, is care about the experience of each of its guests. The staff genuinely cares and there is such a connection to the property that in over 20 years, I can’t recall much turnover of staff. Each member exudes a welcoming presence enveloped in luxury and class. From day one, Round Hill knew that loyalty from its guests wasn’t going to be earned by shallow hospitable greetings or service, but from a deep rooted desire to serve and nurture any guest who entered its gate. And so it has been for 66 years.
You’ll come and bump into Josef, Omar, Jackie, Mark, Kingsley, Stewart, David, and Junior…just to name a few of the Round Hill family members. Josef being the Managing Director is as down-to-earth as is his entire team. This is why you feel at home. There is no separation or visible hierarchy amongst the team, and that bond spills over to each guest. I know you think you won’t need a warm blanket at a beach resort, but you’ll feel comfy and cozy as the overall experience of Round Hill envelopes you in one. The live authentic variety of nightly entertainment, and impeccable seaside dining service punctuates te end of each fabulous day spent at the resort. This is the best of Jamaica as Jamaica was meant to be. The place is timeless and I could go on and on about it, but would rather you get your agendas out and make a plans for your trip to experience all that I am writing about. You can be as chill as you want to be or as active as your body allows. There are water sports to fill your day, from boat rides to water skiing and everything in between. When I wasn’t on a stand up paddle board, I was over at the Welcome Wharf collecting sea glass on the soft white rocks of the beach below the lawn of the spa. This adults only tranquility area is my sanctuary. The two beaches at Round Hill offer me all that I need. One has the gently rounded white stones and the other is my Caribbean sandy beach with water that never seems to go deeper than five feet. Things are so reliable here that even the Caribbean Sea complies. There’s the Beach BBQ night, that kicks off with a welcome rum punch and a stroll past the donkey laden with freshly cut flowers in its basket as the Bantu band plays island classics. Settle in for a real Jamaican feast as later in the evening, your meal will be set to the tunes of a Steelpan band as guests dine on the sand while waves gently creep up to the side of their tables. Looking back across the bay to the Welcome Wharf, the fitness center can be seen. As night falls, it is Illuminated and from this beach, across the bay, it appears to stand sentry, letting you know that all the calories are easily dissolved and all food sins absolved by a short stroll to its open doors.
This is a glimpse of the Round Hill experience. It’s a classic for a reason. Some things never change…Thankfully.