The Side Of Jamaica You Need To See (A Travel Diary)

I have nothing against a spontaneous vacation out of left field (pre-midlife crisis, anyone?), but some getaways need to be more than an all-inclusive package reminiscent of college spring break. And, as a quick look at my vacation photos and passport stamps could affirm, I gravitate toward trips riddled with culture and history over sandy beaches. Why? Call me crazy, but I'm always afraid I'll get bored. One trip to the island of Jamaica, though, and I was proved wrong in more ways than one.
If you want to talk about history, Jamaica had the first railway lines opened to traffic outside of Europe and North America, dating back to 1845. And, records indicate, one of the first-ever, piped-water-supply systems for the western hemisphere originated in the town of Falmouth. But even if textbook history isn't your thing, perhaps you'll be interested in the famous people who have been visiting this part of the Caribbean for generations.
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At Round Hill in Montego Bay, I stayed in a stunning villa, previously owned by Oscar Hammerstein II whose claim to fame was writing the lyrics to the Sound of Music along with pal Richard Rodgers. And right down the road from me was the respite where Kennedy penned his presidential acceptance speech — how cool is that? By the time I made it to the other side of the island, I was living the life of a Bond girl at GoldenEye Hotel & Resort, the playground of James Bond author Ian Fleming.
Of course, what better way to get cultured than by local cuisine? In this case, it was jerk-spiced everything. Chicken, pork, fish — I had it all — and maybe with a little rum punch to wash it all down. So click through my travel diary, and check out the side of Jamaica that doesn't exist on a cruise-ship port.
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Around since 1953, Round Hill Hotel and Villas in Montego Bay was the first resort of its kind in the Caribbean, and it's been a playground for the well-to-do (and famous) ever since. Esteemed socialites like Adele Astaire, Lord and Lady Ednam, Clive and Natasha Wilson, and Clive Brook purchased upscale cottages on the property, making Round Hill what it is today.

The 27 villas are individually owned, by folks such as Ralph Lauren, and are rented out when owners aren't enjoying the lap of luxury themselves. There's also a hotel portion, consisting of suites decorated by Lauren himself.

Photo: Courtesy of Round Hill Hotel and Villas
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The stairway to heaven (a.k.a. my cottage, previously owned by Oscar Hammerstein II).

Photo: Courtesy of Rebecca Taras
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First stop: a dip in the private pool!

Photo: Courtesy of Rebecca Taras
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The living room of the villa — a perfect spot for a group of girlfriends or a few couples to hang out. But in this case, I had it all to myself with a good book in hand.

All of the beautiful villas are distinctly decorated, based on their current owner, so every experience at Round Hill is completely different. Another cottage perk? The staff comes and cooks your breakfast of choice in your kitchen!

Photo: Courtesy of Round Hill Hotel and Resort
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Something to get used to: These doors to my bedroom were the only locking doors in the entire cottage. The living-room area (previously pictured) is completely open.

Photo: Courtesy of Rebecca Taras
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An example of one of the hotel rooms designed by Ralph Lauren.

Photo: Courtesy of Round Hill Hotel and Villas
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No commercial resort here. Round Hill is smack dab in the middle of lush vegetation without a swim-up bar or band shell in sight.

Photo: Courtesy of Round Hill Hotel and Villas
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The Spa at Round Hill is located within a restored, 18th-century plantation house. I participated in a small, outdoor yoga class before heading in for a little R&R.

Photo: Courtesy of Round Hill Hotel and Villas
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While these seaside spa rooms were fine for me...

Photo: Courtesy of Round Hill Hotel and Villa
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Outdoor-table options are perfect for couples.

Photo: Courtesy of Round Hill Hotel & Villas
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I preferred this quiet infinity pool looking over Round Hill Bay.

Photo: Courtesy of Round Hill Hotel and Villas
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Round Hill grows its own organic farm, utilizing the herbs, fruits, and veggies for its farm-to-table Grill Restaurant.

Photo: Courtesy of Round Hill Hotel and Villas
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The gorgeous Seaside Terrace is the scene of the nightly manager's cocktail party (I was full before I even ate my dinner), beachside barbecues, and special events.

Photo: Courtesy of Round Hill Hotel and Villas
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Onto the other side of the island! I made a stop at the "famous" Scotchie's, known for having some of the best jerk food in Jamaica. This particular location is in Columbus Park, which got its name from Christopher Columbus, who stopped there many moons ago.

Photo: Courtesy of Rebecca Taras
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The jerk fish takes an additional 20 minutes. All food is made fresh on site.

Photo: Courtesy of Rebecca Taras
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Welcome to GoldenEye in Oracabessa Bay on the north coast of Jamaica. Author Ian Fleming bought the property and built his dream home shortly after World War II. Eventually, he penned his famous 007 stories, which so many of us continue to love to this day.

Today, the luxurious and remote resort is owned by Chris Blackwell (founder of Island Records), who purchased the Fleming estate back in 1976. Since then, he's transformed the original 19-acre property into a 52-acre resort, serving as the flagship for his other luxurious projects under the name, Island Outpost.

Photo: Courtesy of GoldenEye
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The lobby of GoldenEye is studded with James Bond photos and paraphernalia of all sorts.

Photo: Courtesy of GoldenEye
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Ian Fleming's original home is in a secluded part of the resort that's away from the other cottages. And, yes, it's available for rent.

Photo: Courtesy of Christian Horan
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Lagoon, pool, cay, bar...do you really need to know how to get anywhere else?

Photo: Courtesy of GoldenEye
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After a three-hour trip from Montego Bay, I was ready to relax in my cozy, lagoon cottage!

Photo: Courtesy of GoldenEye
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The back of my cottage had direct lagoon access for swimming or kayaking (kayak included!).

Photo: Courtesy of Rebecca Taras
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From glass-bottom boat tours and paddleboarding to sunset yoga and fishing excursions, being bored is simply not an option.

Photo: Courtesy of GoldenEye
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Paradise, found!

Photo: Courtesy of GoldenEye
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What did I say about not being a beach person? And, yes, the beach here at GoldenEye really stays almost this quiet.

Photo: Courtesy of GoldenEye
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A trip to the Field Spa! I opted to walk, but kayaking is another mode of transportation one can take to get there.

Photo: Courtesy of GoldenEye
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The bridge to get over to all the lagoon and beachfront villas.

Photo: Courtesy of GoldenEye
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Gazebo restaurant, where I enjoyed several, seafood-heavy meals.

Photo: Courtesy of GoldenEye
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A nightcap at Bizot Bar? You bet.

Photo: Courtesy of GoldenEye
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