THIS CARIBBEAN ISLAND RESORT HAS HOSTED ROYALTY,
THE KENNEDYS AND HOLLYWOOD'S A-LIST ELITE
Photos Courtesy of Round Hill Hotels & Villas
Out of Many One People.” This is Jamaica’s multiracial roots-driven national motto that is represented on the country’s Coat of Arms. It is this spirit of togetherness—of
united “oneness” irrespective of race, class, religion age or gender—that has helped Jamaica endure as a revered tourism destination decade after decade. Indeed, this hugely hospitable 4,411 square mile Caribbean Island attracts throngs of visitors to its cities, coasts, rivers and mountain ranges each year.
One of my personal favorite regions attracting tropics-oriented travelers the world over is Montego Bay. As Jamaica’s second largest city, this revered destination has evolved into a tourism beacon reportedly boasting the country’s largest number of hotel rooms. This, in addition to a spectacularly wide range of sports activities, attractions, restaurants, shopping and entertainment options. This city, the capital of Saint James Parish on Jamaica’s north coast, also serves as a major cruise ship port and boasts numerous beach resorts and private villas.
While prolific with hotel, resort and villa accommodations, one luxury area property stands in a class of its own: Round Hill Hotel and Villas. Situated on a lush 110-acre peninsula just west of Montego Bay, this storied boutique resort boasts a historical, celeb- rity-laden pedigree upheld only by the best-in-class. Having recently experienced my own private villa getaway at the destination, I learned first-hand why Hollywood, sports and political A-listers from around the globe flock to this private oasis—one offering guests a secluded, service-focused experience in luxurious island accommodations mere steps away from some of the most beautiful beaches in the Caribbean.
In addition to the 36 Ralph Lauren-designed oceanfront guest rooms in the “Pineapple House” section of the property, Round Hill also notably boasts a selection of 26 private two-to-six-bedroom Villas—most with private pools. Each comes equipped with its own dedicated staff that will prepare daily breakfast and cater to other guest needs.
I had the decidedly good fortune of staying in Villa 16—a spectacularly appointed, sprawling private accommodation with a breathtaking panoramic view of the sea and mountains beyond. This premium luxury villa is one of the largest on property, featuring six of Round Hill’s largest and most expansive suites that, all combined, accommodate up to 14 people quite comfortably.
This private island paradise, replete with landscaped tropical gardens, is the epitome of indoor/outdoor living whether wining and dining, lounging or slumbering. Its expansive pool and surrounding deck is outfitted in classic blue and white lounge chairs, umbrellas and a gazebo. Other favorite features among the various rooms are two lower level bedrooms with see-through windows that peek into the pool; an open-air game room with pool table, ping pong table and wet bar; my own upper floor private master suite with a central balcony proffering magnificent sunset views; and a
MK: What are a few aspects of the property that set it apart from other comparable private villa and luxury resort options in the area?
JF: For one, the legacy and heritage of our villas through the decades sets them apart from other seemingly similar options on the island. Round Hill and its villas stand alone
for having hosted countless icons, such as John F. Kennedy and Jackie Kennedy, Sir Noel Coward, Errol Flynn and Ian Fleming to name a few—and even royalty. Each villa has so many rich stories to tell, which guests are able to connect with during their stay and become a part of that rich and storied history. Second, our staff goes out of their way to not only provide premium levels of service, but also forge meaningful interpersonal connections with guests. I’ve been told time and again that the staff’s gracious hospitality and warm spirits are a major reason that guests continually return to Round Hill. Also, our resort’s familial spirit and culture of “togetherness” truly sets Round Hill apart, which is the culmination of
many unique factors: The history that founders John and Liz Pringle forged since the 1950s; the countless icons that have frequented the resort; our conscientious staff; our majestic surroundings; and more. When guests stay at Round Hill, they are not just staying at a luxury resort but one that allows them to embrace and immerse themselves in a deep and meaningful cultural experience.
MK: Any interesting or unexpected facts about the property?
JF: Well, there are many, but one fun fact that people might not know is that the famed movie “How Stella Got Her
detached guesthouse with its own private infinity plunge pool. Lavish appointments like four poster beds, marble bathrooms and thoughtfully curated art further the multi-sensory experience.
So utterly spellbound by the Round Hill surroundings and staff, I endeavored to connect with Josef Forstmayr—the property’s Managing Director, who, in this role, has been wel- coming guests to the property since 1989. Forstmayr was kind enough to share a bit of his own perspective on what makes this property unique and enduringly beloved by so many.
Groove Back” starring Angela Bassett, Taye Diggs, Whoopi Goldberg and Regina King, among other A-listers, was filmed at Round Hill. Our spectacular Villa 11 served as the backdrop for part of the film. Famed American fashion designer, philanthropist and billionaire businessman Ralph Lauren, who owns multiple of our villas, not only designed the Cocktail Bar but also the décor of our collection of hotel rooms.
Relative to the property’s origin, it was originally a part
of Lord Monson’s Round Hill Estate, which was a sugarcane plantation. The plantation grew coconuts and pimento before Jamaica-born entrepreneur John Pringle turned the property into his dream boutique resort. This it has become for throngs of others since. And, while Round Hill will always maintain its historical iconic pillar, we are in the process of updating and refreshing our collateral materials and website with
an exciting new photo shoot. Our brand new website to be launched this year.
MK: Having served as Round Hill’s Managing Director since 1989, what is your own personal favorite aspect of the property?
JF: The people. It may be cliché to say, but the people truly make Round Hill what it is. The staff consistently upholds the resort’s standard of luxury, while having fun and creating an unmatched atmosphere of excitement and happiness. Round Hill’s guests come with an open-minded attitude looking to experience everything the resort has
to offer; especially different cultural offerings, and to feel wholly taken care of. Without our world-class staff and distinctive brand of island hospitality, Round Hill would not be the iconic destination it is.
his caliber of award-winning service is not by accident. Rather, our property team—even those who have been with
the resort for many years—not only receives ongoing training from our own property leaders, but also from a number of other companies we bring in to reinforce training on how to exceed guest expectations. Round Hill has always been known as a resort with warm and friendly staff who go above and beyond for our guests, which is why our repeat guest factor is so high.
As well, we are always finding ways to incorporate the latest technology into the guest experience in an organic way to add and elevate convenience. We recently launched a new mobile app, for instance, that allows for a more seamless arrival and on-property experience, where guests can complete a mobile check-in, make pre-arrival requests and learn more about
on-property programming both before and during their stay. We are also continually evolving our amenities to cater to
changing guest demands. For example, given the rise in requests for pickleball, we recently decided to convert two of our tennis courts into pickleball courts to provide an extra activity that our guests can enjoy on-property.
We also look for new ways to enhance the arrival and depar- ture experience for travelers. As one case in point, guests staying in one of our “Signature” or “Estate” Villas also enjoy access to the Club Mobay VIP airport service, whereby a representative will expedite them through the airport upon arrival and departure for a stress-free experience. Club Mobay also provides guests with access to a VIP lounge equipped with snacks and refreshments.
In my own personal experience on-site, I can say that Round Hill’s accommodations, décor and amenities blend timeless comfort with state-of-the-art convenience. This, combined with an unrivaled service standard, allows guests to settle into a resort that genuinely feels like their own home-away-from-home—whether vacationing for pleasure or visiting for remote working needs. One stay of your own and it’ll surely become crystal clear why this dreamy destination has endured for decades as the crème-de-la-crème of a luxury Caribbean Island vacation.
