I Embarrassed Myself in Jamaica

Since Oyster staff is on a COVID-19 travel hiatus for the time-being, we thought it would be fun to look back at some of the ways big and small that we've embarrassed ourselves on trips over the years. Sure, we're professional hotel reviewers, photographers, and travel writers -- but we're also human and sometimes we make travel mistakes along the way. Here's how I embarrassed myself in Jamaica.

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View from Round Hill Hotel & Villas
View from Round Hill Hotel & Villas/Oyster

Driving on the Left in Jamaica

When I was assigned to review two luxury hotels in Jamaica, I was pretty excited. I’d never been to the Caribbean island before, and was eager to experience the local culture, swim in the warm sea, and catch stunning sunsets in between photoshoots and tours.

My Jamaica itinerary included a few nights at Jamaica Inn, on the beach in Ocho Rios, followed by two nights at the Round Hill Hotel and Villas on the outskirts of Montego Bay. The hotels are about a two-and-a-half hour drive apart, so I decided renting a car on arrival at the Montego Bay International Airport would be the easiest and most affordable way to get around.

Reader, this where it gets embarrassing.

Jamaica is part of Great Britain’s commonwealth, so I knew that the islanders drive on the left-hand side of the road. No big deal, I thought. I’d confidently driven myself around Costa Rica’s volcanos, Santorini’s cliffs, Cabos’ motos, Paraguay’s donkey carts, and New York City’s cab drivers — perhaps the diciest driving test of them all. But as I pulled my rented sedan out of the airport parking lot and on to the left side of the airport road, I panicked. Every instinct and brain cell was screaming that I was Driving. On. The. Wrong. Side. Of. The. Road.

It’s here that I should mention Sean, the otherwise very friendly car rental agent, was not happy with the idea of renting me a car in the first place. He explained that he’d never rented a car to a single woman, and suggested I wait until he finish his shift so that he could personally drive me the hour to Ocho Rios. I politely declined. I couldn’t tell if Sean was hitting on me, sexist, or truly worried for my safety. To appease him, I gave him the phone number of the hotel so that he could call later and check on me, and he begrudgingly handed over the keys.

Back to the left-hand side of the road. I briefly considered driving the five minutes to Jimmy Buffett’s Margaritaville and admitting defeat with a super-size margarita, but instead I pulled myself together and came up with a game plan. The drive from the airport to Ocho Rios is mostly a straight shot with a few roundabouts, so If I just followed the car ahead of me, my mammalian brain could feel like part of the herd and I’d be able to drive safely. This plan went swimmingly. I even managed to admire the gorgeous coast and sprawling all-inclusive resorts that make Jamaica one of the most popular Caribbean islands. Then, I hit my first hard turn on a roundabout traffic circle and embarrassed myself completely.

Instead of turning right into the left-hand lane, which would essentially be suicide in America, I panicked and couldn’t turn at all. I flipped off my turn signal, realized it was actually the windshield wipers, and just kept driving in circles around the roundabout. Luckily, the traffic was minimal, and I was driving slow (albeit still with the windshield wipers going). I couldn’t make myself turn into the opposite lane. So what did I do? I turned off on the wrong exit, away from my hotel. How embarrassing.

Trying to Use GPS in Jamaica

Remember Sean, the overly-friendly car rental employee? Along with the sedan, he also rented me a dashboard GPS, with a warning me that it probably wouldn’t work, since Jamaica’s 3G signal is spotty. I had a smartphone and Google maps, but encountered the same “no signal” problems. Thankfully, Sean provided me with an illustrated tourist map, and circled a few landmarks so that I would know I was headed in the right direction. I’d smiled and breathed a sigh of relief as I passed Runaway Bay and the sign for Dunn’s River Falls and Park. The GPS was silent and my phone had no service, but the map was doing me right. I’d be at the hotel in no time.

Until I took the wrong turn. Instead of turning onto a quaint touristy road filled with shops and jerk shacks, I got on Highway 2000. Which…would take me straight through the center of Jamaica and towards Kingston — not where I wanted to go. And now I was off of the tourist map entirely, and without a GPS signal. Thankfully, I only drove a few miles before there was an exit that allowed me to turn around and get back on track. The fear of almost driving myself to Kingston overrode the fear of making a hard turn, and I almost kissed the ground when I saw the sign for Jamaica Inn. If you’re wondering, Sean did call to ensure my safe arrival.

Not Knowing What Jerk Chicken Is

This is embarrassing, but before I went to Jamaica I didn’t really know what jerk chicken was. Sure, I had heard of jerk chicken, but I wrongly (and to my embarrassment) assumed it was dried meat — like beef jerky. Luckily, the waiter at The Terrace at Jamaica Inn lovingly set me straight. He explained that jerk is a traditional and celebrated style of cooking and spices used to season chicken, and it can also be used to add Jamaican flavor to fish, seafood, pork, and beef. The meat is coated in hot peppers and spices and then slow-cooked over a grill of green pimento wood; the resulting smoke is the key to Jamaican jerk flavor.

Jerk chicken is way better than any jerky I’ve tried, and jerk is easy to find all across Jamaica. Locals love to eat it with a cold bottle of Red Stripe at casual jerk stands near the beach. We’re talking a few benches and tables in front of an open-fire levels of casual here. Jerk is also served as an elevated art form at fine-dining restaurants in all-inclusive hotels, usually with multiple vegetable sides and beans and rice. One of the most popular place’s to try jerk is at 3 Dives Restaurant and Cliff Bar in Negril. Expect weekly live music and nightly bonfires. Don’t tell anyone you thought jerk chicken was dried meat.

Horseback riding on the beach at sunset
Sunset horseback riding; Austin Neill/Unsplash

Horseback Riding in the Water

I didn’t have a lot of time or money budgeted for excursions on my Jamaica trip. My plan was to spend any free time walking on the beach, swimming in the pools, and sipping rum punch at the outdoor bars. But. Before I left, I has seen so many gorgeous Instagram photos of tourists horseback riding in the water that I had to try it for myself. The front desk staff booked me a spot for the following day and I was instructed to wear a bathing suit underneath a pair of shorts and a shirt, plus a pair of water sandals or shoes. No flip-flops. I was excited to meet my horse and have the once-in-a-lifetime experience of riding on a swimming horse in the Caribbean.

Of course, this didn’t come off picture-perfect either. First, I was the only single person on the excursion. I was surrounded by honeymooners and families, and no one had much interest in talking to me. I felt awkward and suddenly very silly to be in Jamaica by myself (even though I was there to review hotels for work). Second, before we got to the swimming part, we took the horses on a long trail ride through scrub pastures. The scenery was pretty, with the Blue Mountains in the distance, but it was uncomfortable to ride a horse in shorts (don’t try it) and the sun was insanely hot. When we got to the scenic part of the ride where the horses could run on the beach and in the surf, I realized that the horses also use this part of the ride to relieve themselves. Like, in the water…where the evidence floated and accumulated. Some of the honeymooners were lifting their legs to dodge floating horse poo.

When it came time for the main reason we all spent $200 on this excursion, the free-range ocean horse swim, all the riders had to put on embarrassingly ugly and old life jackets. It was super cool to feel a horse swimming in the ocean underneath me, and I’d never ridden bareback before — but riding bareback with a lifejacket just ruins the whole vibe. I did not want photographic evidence. Though I was suddenly very popular amongst the other tourists who originally ignored me, but now realized I was widely available to take photos of them holding hands on top of their horses. I wonder if any of them look back at their honeymoon pictures and wonder what I was doing in Jamaica by myself.

Skipping a Sunset Catamaran Cruise

Had I planned my trip more thoughtfully, I would have chosen to take a sunset catamaran cruise instead of the horseback swim excursion. The catamaran cruises have a fun party atmosphere that’s way more singles-friendly. Along with unlimited rum drinks, conch snacks, and a crew trained to party and flirt, the catamaran cruises offer a chance to swim, snorkel, and take in Jamaica’s gorgeous sunsets from the Caribbean. And, there isn’t any mammal fecal matter in the water.

Aerial view of a road in Jamaica
Road in Jamaica/Oyster

Returning Too Early to the Airport

Once I checked out of Jamaica Inn, I had to brave the left-handed drive back through Montego Bay to get to the Round Hill hotel and Villas, which is isolated from the main drag and has its own private beach. I was no longer worried about driving on the left-hand side of the road. Now I was worried about getting lost and driving myself to the Bahamas (impossible, I know). Of course, I got lost again. This time, instead of panicking, I humbled myself and smartly pulled up to the security checkpoint at Secrets St. James Montego Bay. I knew the guard would be a safe person to talk to, and used to dealing with American tourists. I was right. He gave me very clear directions to the Round Hill and I was on my way, only a touch embarrassed.

After two nights enjoying Round Hill (I think I only embarrassed myself once by assuming a young woman was an older gentleman’s daughter at the bar — she was his wife), it was time to return the car and fly back home to Los Angeles. I was looking forward to seeing Sean again and telling him he’d been kind of right about me driving, but also wrong, because I got everywhere safe and sound (just a little delayed). But to my embarrassment, I got to the airport super early (I’d budgeted in way too much extra time for getting lost, which didn’t happen at long last) and the car rental agency wasn’t yet open. I had to leave the car keys in a mail slot, which made me a bit nervous, since car rentals are notorious for claiming damage and I would have felt better speaking with an employee.

I worried for no reason. The car was properly returned, and Sean friended me on Facebook a few days after I got back to the states.

Our Jamaica Hotel Pick: Round Hill Hotel and Villas

Pool at the Round Hill Hotel & Villas
Pool at the Round Hill Hotel & Villas/Oyster

When it’s safe to travel again, Round Hill Hotel and Villas is worth embarrassing yourself for a visit. It’s a phenomenal luxury property with a gorgeous private beach, about a 30-minute drive from the airport in Montego Bay (organize a hotel transfer service, trust me). Visitors stay in charming ocean-view rooms designed by Ralph Lauren. Each has a four-poster bed, coffeemaker, air-conditioning, and locally made toiletries. For more privacy, 27 individually-owned villas feature living spaces, classic decor, and pools in most. Expansive grounds house a truly stunning infinity pool, lovely spa with an outdoor pool and adjacent fitness center (there’s a dedicated trainer who is happy to critique your form), lawns with daybeds, a kids’ club, and TV room with games and movies. Dining is excellent, and I particularly liked the beach barbecues (hello again, jerk chicken) and free afternoon tea with snacks. Some of the guests I encountered have been traveling to the hotel for decades to enjoy the beach, food, and excellent Caribbean vacation ambience. I wonder how many times they’ve embarrassed themselves in Jamaica.

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