Round Hill Hotel & Villas Jamaica’s Top Resort

You can imagine my surprise when I looked over at the next table, while having lunch on Round Hill’s panoramic seaside terrace, and saw our USA Secretary of the Treasury Janet Yellen and her family. They were laughing and nibbling on fresh salads from the resort’s organic gardens, as a dozen Secret Service agents tried to blend into the foliage. The resort is no stranger to VIPs—I just missed Michael Douglas and Catherine Zeta-Jones, who were here for a wedding the week before. No one does “I do” festivities better than Round Hill.  I accidentally witnessed a glowing couple say their vows with the sea behind them before having a glamorous party on the beach with 100 friends as I was leaving the resort’s world-class spa. If you like yoga, ask for Donavan, and there are delightful masseuses who do reflexology, massage, and perfect mani-pedis.

 A Storied Past

Originally, Round Hill was part of a sugarcane plantation owned by Lord Monson. Round Hill resort was the brainchild of John Pringle, a Jamaican-born entrepreneur whose socialite mother owned a hotel in Montego Bay. Pringle served in the British Army, worked for Elizabeth Arden in New York City, opened a haberdashery, and after marrying and having kids, returned to Jamaica. Round Hill opened in 1953 with Noel Coward as its first shareholder. Today, VIP shareholders include shoe designer Vanessa Noel and Blackstone founder Stephen Schwarzman and his wife, Christine Hearst Schwarzman.

 Meet the Hotelier

In his office at Round Hill, the managing director, Josef Forstmayr, has a glorious letter from Queen Elizabeth II, naming him Jamaica’s honorary Consul General for Austria. Among the many famous guests at Round Hill, Forstmayr is especially fond of Goldie Hawn and Kurt Russell, and Sir Paul McCartney, who has been coming to the resort for many years. “All of Paul McCartney’s children grew up here: Stella, Mary, James, and Heather. They all used to spend every Christmas here, and he’s an incredible person.” Forstmayr currently serves as the director of the Jamaica Tourist Board, the Montego Bay Chamber of Commerce, and he chairs the Montego Bay Arts Council.

 From Astaire to The Sound of Music

Adele Astaire, Fred’s sister and dance partner, owned one of Round Hill’s villas, Number 25, that was later used by JFK. Kennedy actually edited and rehearsed his presidential inauguration speech there, and parts of it are still displayed in the cottage. Oscar Hammerstein owned Villa 12 and met the real-life Maria Von Trapp there. He wrote The Sound of Music, as well as several other musicals, in the three-bedroom property.

More recently, Angela Bassett, Whoopi Goldberg, and Taye Diggs lounged in the private pool while taking in the spectacular hillside views of the Caribbean from Villa 11, the set of the 1998 movie How Stella Got Her Groove Back. A few years later, Diggs and Idina Menzel had their wedding at Round Hill.

Prince Harry & Meghan Markle

 In 2017 Prince Harry brought along his then-girlfriend Meghan Markle for the wedding of his best friend and former wingman Tom “Skippy” Inskip. The visit was important because attending the Round Hill nuptials took their relationship to the next level, since Markle met the prince’s closest friends. Harry served as an usher. Several months later Harry and Meghan announced their engagement. There’s definitely something about the seaside air at Round Hill.

The couple stayed at Cottage 16, the same one in which author Ian Fleming, creator of James Bond, stayed. The glamorous, ultra-private villa has six bedrooms, two pools, and stunning views of the Caribbean, with decor by Ralph Lauren.

Harry and Meghan loved hanging on the beach, and their villa was equipped with a state-of-the-art kitchen where the future Duchess of Sussex could whip up dinner for her prince. That’s if she wanted to cook—Round Hill’s villas come fully staffed with a designated chef, a housekeeper, and a gardener. You really don’t have to lift a finger at this resort, except to raise a flute of champagne to your lips.

High Rock

Ralph Lauren designed the 36 luxurious ocean-view guest rooms at The Pineapple House, the main hotel at Jamaica’s Round Hill Hotel and Villas, but this was no mere interior design gig. It was a labor of love. “The greenness of Jamaica is gorgeous,” pronounced the designer. “The air is very mild. It feels like a paradise. There’s a naturalness and ease of living. It smells like a beautiful place.” Lauren and his wife, Ricky, own two of the 27 villas on the lush 110-acre property. One, called High Rock, sits on the resort’s highest point: “We made the house what it should be,” Lauren said of the place he’s owned for more than thirty years. “It’s in the spirit of Round Hill—very quiet, very elegant.”

White Orchid

The other, White Orchid, which they purchased in 1996, is down the hill, directly on the beach, and was once owned by William and Babe Paley. Lauren decorated this one with a classic feel. “The White Orchid is clean, barefoot, and luxurious,” he said. “It’s like being on a boat.”

Ralph Lauren has put his stamp of approval on Jamaica as a vacation destination, according to Josef Forstmayr, Round Hill’s longtime and popular managing director who worked with the designer on its recent update.  “We go there as often as we can escape,” said Ricky Lauren, who penned a book about Jamaica titled My Island.

Vogue called one of Lauren’s runway shows, complete with wicker chairs, tropical plants, and woven basket patterns, a “love letter to his Round Hill, Jamaica home.” Lauren’s show notes read: “Everyone wishes for a magical place where they can step out of time into the beauty of nature. For Spring, I wanted to share the mood, the light, the blue-and-white freshness of my retreat in Jamaica.”  An unofficial ambassador for the island nation, Lauren was named an Honorary Commander of Jamaica’s Order of Distinction, and his face appeared on a postage stamp, an honor shared by Winston Churchill and Princess Diana.

Justin Bieber, Jacqueline Kennedy & Noel Coward

Round Hill is Jamaica’s most personal, elegant, and private resort, and Lauren was not the first bold-faced name to discover its charms. John and Jacqueline Kennedy honeymooned at a seaside cottage at the resort. James Bond author Ian Fleming, Errol Flynn, and Noel Coward, all visited before later buying their own homes here. During the 1950s and ’60s, Princess Grace Kelly, Claudette Colbert, Clark Gable, Yul Brynner, and Alfred Hitchcock could be found sunning and swimming at Round Hill.  Visitors have also included Paul McCartney and Pierce Brosnan. Justin Bieber, before marrying Hailey Baldwin, was once seen kissing Selena Gomez at the resort, before taking her on a bamboo raft down the island’s Great River with Chukka Caribbean Adventures.  chukka.com 

Ultimate hospitality

Round Hill has its own concierge at Montego Bay’s airport, ready to assist you and arrange private transportation to the resort, about 20 minutes away. Before our trip, they sent us a full, written itinerary for our stay. How perfect!

Our villa included a daily New York Times, afternoon tea, full use of the fitness center with instructor, non-motorized water sports, shuttle to Tryall Golf Club, and supervised activities for kids, if you need it, all at no extra charge.

Dinner on the Beach – with candles and tablecloths

What an unexpected and fun surprise on our first evening! It turns out that Mondays are designated for beach barbecue parties, and longtime general manager Josef Forstmayr continues the tradition in signature Round Hill luxury style. This means tables with red tablecloths, candles, and fine silverware set on the beachfront, while buffet tables with various cuisines are placed under trees. We had fresh corn, chicken, brisket, and sautéed shrimp. Executive Chef Martin Maginley oversees everything, and much of the produce is grown in the resort’s organic gardens.

Cottage 12

On this trip, we ended up in Cottage 12, now owned by shoe designer Vanessa Noel. The cottage is perched high on the hill with magnificent views of both Round Hill Bay and Montego Bay. The charming, secluded villa boasts three ensuite bedrooms, living and dining rooms, and expansive terraces with breathtaking views. We had our very own large pool set in a lush green garden.  The cottage comes with its own staff, a chef, housekeeper, and gardener. Needless to say, everything was always immaculate, and what fun it was to order banana pancakes for breakfast or any time we chose.

In-Villa Dining:

While there are several dining options, the cook in your villa will pamper you. Start your day— whether you’re up with the roosters or sleeping in until midafternoon—with those aforementioned insanely delicious banana pancakes accompanied by freshly brewed Jamaican Blue Mountain coffee on your private patio overlooking the sea. Try the cinnamon French toast, coconut pancakes, fresh tropical fruit plate, or more traditional breakfast dishes like omelets and cereal.

Of course, they serve up authentic Jamaican breakfasts with dishes like ackee, a gorgeous tropical fruit and saltfish, which is cod, or organic callaloo, a leafy green, with boiled ground provisions called yams.

You literally do not need to leave your villa. You can eat all your meals there in total privacy. Lunch offerings include a variety of soups with local flavors, including pumpkin chicken and vegetable pepper pot, organic salads, wraps, fresh fish, and fried chicken.

Among the in-villa dinner dishes, you’ll find fresh steamed Caribbean fish, shrimp or vegetable curry, pastas with local vegetables, and chicken prepared in various ways, including barbecue and jerk. I’m getting hungry just thinking about it. If you want to go to the dining room, consider Jamaican night, an expansive buffet with all the local specialties, including oxtail, fish escovitch, and red pea soup.   

Alligator Park

After breakfast it’s fun to go exploring; be sure to check out the alligator farm and zoo at Jamaica Swamp Safari Village that’s close to Round Hill.  Here you will see a variety of indigenous animals, including snakes, parrots, other birds, monkeys, raccoons, and even a boar. If you ask and tip a little bit, the guide will get some big hunks of beef to feed Sammy B. the one-thousand-pound alligator that lives in his own pond. The James Bond movie Live and Let Die was filmed here, notably the scene where Roger Moore escapes over the backs of several alligators. It’s fun to Google the video on your phone while you are there.  my-island-jamaica.com

Rose Hall, Haunted House

If you like history, definitely go to Rose Hall, a Georgian-style 18^th-Century plantation “Great House,” probably the most famous in Jamaica. Completely restored in the 1960s and furnished with antiques, the historic house and extensive grounds are open for tours and located near Round Hill.

According to legend, Rose Hall is haunted by Annie Palmer, a “white witch” who murdered three of her husbands. Married to John Palmer, who owned the plantation until Annie murdered him, she is also said to have offed her two subsequent spouses, as well as some of the plantation’s residents. The legend goes that one of the residents later murdered Annie.

Johnny Cash recorded a song called “The Ballad of Annie Palmer,” with the lyrics: “Where’s your husband, Annie, where’s number two and three

Are they sleeping ’neath the palms beside the Caribbean Sea?

At night I hear you ridin’, and I hear your lover’s call

And still can feel your presence round the great house at Rose Hall.”

It is claimed that she still walks the property, and so strong is her curse that no one has dared sleep there since the 1980s, when a couple got scared off by the ghost. Annie is buried there, and by the ocean under three palm trees lie her three murdered husbands. Rose Hall even offers haunted night tours, not recommended for children under ten. rosehall.com

Restaurants – Farm-to-Table

The Grill

By now you’ve probably worked up an appetite. The Grill is Round Hill’s rooftop dining spot, where you can enjoy the balmy ocean breezes while taking in the panoramic views. The food here is “modern Caribbean,” much of it locally produced, with snapper, grouper, and local lobster straight from the sea. Ingredients are organic and sustainably grown.

Seaside Terrace, Barefoot Elegance

This stone terrace overlooking the sea serves lunch as well as other themed meals, including a Caribbean curry night on Wednesdays, and authentic Jamaican food on Fridays with a popular live show appropriate for all ages. Highlights on the Jamaican menu include “firecracker” coleslaw, gazpacho shooters, jerk chicken, braised oxtail, and crispy fried conch, plus terrific vegetarian options. Desserts are homemade, and there’s a flambé station with Jamaican rum. Tip: the à la carte menu is always available as well, so you can join in the seaside fun, and you won’t go hungry if the day’s cuisine is not to your taste.

The draw here is an informal and fun lunch and dinner, but with elegant touches like candlelight and tablecloths. “Barefoot elegance” best describes the ambience. The menu here highlights James Beard Award-winning chef Martin Maginley’s clean Caribbean cuisine, updating classic dishes from the 1950s, when the resort was founded, including lemongrass lobster bisque, grilled tuna filet, beef Wellington, and his signature Scotch bonnet ice cream.

Afternoon Tea

Round Hill’s ultimate experience is Teatime. It is served daily at 4:00 p.m. in the lounge, perfect for a break from the sun or to meet friends old and new.  The tea fare is traditional, with perfect cucumber sandwiches, fruit, and pastries. Try the chocolate chip cookie and the tiny brownies, a decadent delight. Check out the black-and-white photographs of famous guests—such as the McCartney family and Ralph Lauren—from the past dotting the walls of the Round Hill’s Cocktail Bar, the perfect place for pre- or post-dinner cocktails, with sunset views and a musician tickling the ivories. Round Hill is Heaven.  roundhill.com