“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, celebrity-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 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 welcoming 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.
MK: First, let me ask who Round Hill caters to. Who do you feel is your target or ideal clientele?
JF: Round Hill has a legacy of creating lifelong guests and we continually strive to serve as a haven for our guests to return to time and time again. Given the intimacy of our facilities and the privacy that our villas and other accommodations provide, our ideal clientele consists of guests and families that are looking for the solitude and creature comforts of a home away from home. We appeal to couples, groups of friends and multigenerational families who seek luxury seclusion, while our staff provides a welcoming charm that makes guests feel as if they are part of the Round Hill family. Rather than “one and done” experiences, we want our guests to create a tradition of frequenting Round Hill and passing that down for generations to come.
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, Ian Fleming, 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: The pandemic obviously presented its fair share of challenges for everyone in the travel and tourism sector. How will Round Hill continue to navigate associated difficulties?
JF: Round Hill was built with privacy and seclusion in mind, so our pristine villas and discrete facilities naturally lend themselves to notions of social and physical distancing that were spurred by the pandemic. So, we’re already perfectly designed and positioned for guests who are desiring the ability to limit interactions with others and practice physical distancing … not just in-room, but across our expansive property. Additionally, we’ve continued to adhere to the health and safety protocols our team introduced at the height of the pandemic to ensure both our guests’ and staff health and safety, while also adapting to changing government guidelines and regulations to ensure utmost compliance.
To help assure guest health and safety up ahead, and confidence related thereto, we will continue to put an emphasis on privacy and seclusion, which have always been part of our property’s value proposition, as well as following our own rigorous health and safety programming and protocols. Additionally, relative to points of service, Round Hill continues to offer guests the convenience and privacy of on-site COVID-19 testing led by an area physician to help them align with any ongoing global travel requirements, and we have isolation protocols at-the-ready on-property for any guests who may test positive.
Especially in a post pandemic world, we want to emphasize secluded luxury; the privacy our property affords to guests in combination with our staff’s exceptional dedication and attention to detail that, all combined, provides a seamless and exclusive guest experience.
MK: An increasing amount of attention is being paid to “socially responsible travel” and I know Round Hill is mindful of this. Can you share a bit about Round Hill’s own practices?
JF: The property’s dedication to social and environmental responsibility is something that the resort has always been committed to, but it is not always something guests see when they stay with us. Round Hill has many eco-friendly initiatives in-place to reduce the property’s carbon footprint and preserve the surrounding nature and wildlife. Key priorities include waste reduction energy efficiency, farm-to-table consumption and localized purchasing. For example. our culinary team uses many herbs, vegetables and fruits that are grown in the property’s very own organic garden without using harsh pesticides. Other vegetables, like kale and arugula, are purchased directly from local schools, which grow them with the help of the local One Love Foundation’s School Yard Garden Project. The property also works closely with Seascape Caribbean, which helps preserve the local coral reefs. The organization helps train local fisherman to become coral gardeners, helping to rebuild those ecosystems, which are so vital to the island.
Other examples of our “green” practices include the use of photocells and CFL’s where appropriate; use of natural ventilation and ceiling fans rather than relying upon energy-intensive air conditioning; timers on all pool pumps to reduce utilization of electricity; reduced use of paper napkins, straws and coasters to eliminate unnecessary waste; a linen re-use program at the discretion of our guests; and utilization of our own wastewater treatment plant to collect all waste on our property.
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 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.
This 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 departure 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.
Forbes Business Council, Newsweek Expert Forum and Rolling Stone Culture Council Member Merilee Kern, MBA is an internationally-regarded brand strategist and analyst who reports on cultural shifts and trends as well as noteworthy industry change makers, movers, shakers and innovators across all categories, both B2C and B2B. This includes field experts and thought leaders, brands, products, services, destinations and events. Merilee is Founder, Executive Editor and Producer of “The Luxe List” as well as Host of the “Savvy Living” lifestyle TV show that airs in New York, Los Angeles, San Francisco, Miami, Atlanta and other major markets on CBS, FOX and other top networks; as well as the “Savvy Ventures” business TV show that airs nationally on FOX Business TV and Bloomberg TV. As a prolific lifestyle, travel, dining and leisure industry voice of authority and tastemaker, Merilee keeps her finger on the pulse of the marketplace in search of new and innovative must-haves and exemplary experiences at all price points, from the affordable to the extreme. Her work reaches multi-millions worldwide via broadcast TV (her own shows and copious others on which she appears) as well as a myriad of print and online publications. Connect with her at www.TheLuxeList.com and www.SavvyLiving.tv / Instagram www.Instagram.com/LuxeListReports / Twitter www.Twitter.com/LuxeListReports / Facebook www.Facebook.com/LuxeListReports / LinkedIN www.LinkedIn.com/in/MerileeKern.
Some or all of the accommodations(s), experience(s), item(s) and/or service(s) detailed above may have been provided or arranged at no cost to accommodate if this is review editorial, but all opinions expressed are entirely those of Merilee Kern and have not been influenced in any way.
All images Courtesy of Round Hill Hotels & Villas