We started with a quick overnight at S Hotel Kingston where we indulged in a few too many Red Stripes (Jamaica’s local beer) while listening to live music at the rooftop restaurant at our hotel. We hit the sack early to be ready for the first leg of our road trip the following day.

We rented our car from Garmack Car Rentals, just a few minutes from our hotel. The owner is a friend of a friend, and he made sure we were ready to go with the correct route and driving tips.

Off we went, ~3 hours to our destination, Jakes in Treasure Beach.

Driving in Jamaica is an adventure, but it is doable – just keep the following tips in mind!

• Depending on where you’re driving, roads can be narrow, windy, and very bumpy. Take your time, pay attention, and do your best to avoid driving straight into a pothole. It almost feels like you’re playing a real-life video game, weaving around the holes in the road while navigating the twists and turns.
• Don’t worry if you hear someone honking at you from the opposite direction. They are just giving you a heads-up that they’re coming. Many of the narrowest roads are actually 2 lanes, so it is considered courtesy to hit the horn for a second and let people know you’re there.
• Because there aren’t a ton of highways, the narrow, back-roads serve as the main transportation route for many larger trucks. You will, no doubt, get stuck behind a few here and there, which can seriously slow you down. It’s completely fine to pass them, but make sure you wait for a relatively straight road that gives you a clear view of oncoming traffic.

We were thrilled when we arrived at Jakes – it is a treat! Its accommodations vary by proximity to the ocean and price, but they are all designed with joyful colors and patterns. We splurged on an oceanfront bungalow at the edge of the ocean, featuring floor-to-ceiling views, a private outdoor shower, and a roof deck perfect for stargazing.

Jakes has a couple of beach options for those who enjoy a chill beach day, a restaurant serving authentic Jamaican cuisine, pools, and of course, a bar making the freshest pina coladas.

We also indulged at Jack Sprat Restaurant & Bar for dinner one evening, a short walk from Jakes.

I’ve read a lot about Jamaica over the years, and one place I’ve always dreamed of going was Floyd’s Pelican Bar. Sure, some may call it a bit touristy, but it’s a very cool and very well-executed concept – it’s a bar, built on stilts and only accessible by boat, located about 3/4th of a mile off the coast of Jamaica.

It was started by a local fisherman in 2001 and has gained popularity over the years as a remote spot to drink a Red Stripe and swim in the perfect blue waters of the Caribbean Sea.

Getting there and back is a fun adventure! We walked a few minutes down the road from Jakes to a beautiful beach filled with local boat operators who are extremely skilled at navigating the choppy waters to Floyd’s. Our ride was a no frills, motorized wooden boat that happened to be a striking teal color. The ride to Floyd’s was relatively smooth, but the ride back – not so much. We were bouncing up and down, side to side, with water ferociously spraying us in the face. It was a blast.

Our next drive was ~2.5 hours to Villas Sur Mer in Negril. I was up at the wheel. I think my husband and our friends were more terrified than I was, but after some stunning coastal driving (and maybe hitting a few too many potholes), we made it there in one piece.

We planned this trip a bit late so, unfortunately, all oceanfront accommodations were booked, but Villas Sur Mer did not disappoint! We stayed in a spacious villa surrounded by lush vegetation with a serene pool and bar located in the back of the property. Although we weren’t directly oceanside, the property has a unique tunnel built under the road that opens up to the majestic rocky cliffs and blue water of Negril.

Culinary highlights:

• Patsy’s Coffeeshop serving yummy breakfast (American or Jamaican) with quite the view
• Pushcart Jerk Center & Rum Bar is Rockhouse Hotel’s more laid-back restaurant serving all the Jamaican classics.
• Woodstock Lobster Shack, directly on the beach with nice food
• Right next to our hotel and with gorgeous views rivaling those at the famous Rick’s Cafe but without the chaos, LTU Cliff Bar and Restaurant fed us on numerous occasions.

Other fun highlights:

• Although, I don’t find sitting on a beach all day overly exciting, we posted up at Seven Mile Beach (specifically, Alfred’s Ocean Palace) to accommodate our beach-loving friend. I’m not going to complain about splashing around in the most pristine water with a pina colada in hand.
• A night at “The Jungle,” Negril’s popular nightclub that draws a nice mix of locals and tourists… We drank, we danced, and we met some interesting people.
• If you know anything about tourism in Jamaica, you’ve probably heard about Rick’s Cafe. It’s a chaotic, loud, bustling spot, but it is positioned beautifully to view Jamaica’s world-renowned sunsets. It also has a 35-foot cliff jump that is terrifying. I’m afraid of heights, which I tried to overcome while skydiving in Queenstown, New Zealand (read about that here), but for some reason, I still have trouble with cliff jumping. My friend and I had a grand time watching our husbands jump, and next time, I am determined to do it!

Another highlight from our time in Negril was the Rastafari ATV tour. We got picked up from our hotel and shuttled deep into the jungle where we learned how the locals live, imbibed in some delicious rum drinks, swam in mineral pools, drove ATVs, and were served a traditional vegetarian lunch.

When it was time to depart, we drove ~2 hours to Montego Bay, one of Jamaica’s busiest tourist hubs. We didn’t stick around because it mostly consists of resorts and Margaritavilles.

Before boarding our flight, we sat in the airport drinking our final Red Stripes and soaking in the chill, friendly vibes that we had experienced all week and promising that we would try to channel those as we returned to our chaotic lives in NYC.