Off the Beaten Path in Jamaica

Prior to our trip, I had scoured the internet sifting through articles, blog posts, and photos that revealed more about the mysterious Eastern side of Jamaica. Who dared venture past the comforts of an all-inclusive resort in Montego Bay or Negril? Would the other half of the island be as unspoiled as I'd hoped?

I had read that Port Antonio can be challenging to reach. Although the week before Christmas is a less popular time on the island, there was no shortage of locals driving recklessly around hairpin turns. Coupled with storms, road closures, shady Google Maps directions, and driving on the left side of the road, our drive from Montego Bay to Port Antonio was arduous.

It was dark and damp by the time we reached our destination. A collection of villas nestled on a hill overlooking the Blue Lagoon, Tropical Lagoon Resort quietly awaited us with open arms. I knew immediately by the dissonant chorus of frogs and crickets that our trek had been worth it.

Despite being the less-traveled part of Jamaica, there were still endless opportunities to drop a lot of cash quickly. Locals were quick to push excursions like guided tours of the Blue Mountains, rafting down the Rio Grande, snorkeling at Monkey Island, and visits to the areas waterfalls. When surrounded by so much natural beauty, it's easy to become overwhelmed and feel the desire to attempt to see it all.

As enticing as all of these excursions sounded, I was more interested in experiencing Jamaica slowly. Fortunately, Tropical Lagoon Resort included a small private beach with access to the Blue Lagoon. It was simple, quiet, and I spent the good part of our first afternoon bingeing on podcasts from there.


Nothing about navigating the Port Antonio area of Jamaica felt easy. By the end of the second day, our rented Toyota Yaris had seen its share of unpaved roads, steep hills, rocky terrain, and unexpected obstacles (goats! feral dogs! locals on bikes!) Luckily, my boyfriend enjoys these kinds of difficult driving conditions and we were able to explore on our own schedule.


Winnifred Beach, recently featured on Anthony Bordain's Parts Unknown, is one of the area's only remaining free beaches. Its rugged beauty contrasts the idyllic white sand and pristine aquamarine waters of the area's private beaches. Surrounded by jungle, the trees embrace the coastline, sprinkled with brightly colored shacks pushing local eats. Winnifred is where the locals hang out and it's stunning.

We scored some tasty chicken paired with rice and plantains ($10 each) and floated around in the warm waves until dusk. I had heard this beach is generally packed and noisy with families on the weekends, but it was serene on a Wednesday afternoon. Unspoiled, indeed.


The town of Port Antonio was loud and dirty with R&B and reggae blasting from the windows of slowly passing cars. Almost all of the roads were in the process of being repaved and several spots were still caked with mud from the previous day's storms.

By mid-day Saturday, temperatures had swelled into the 80s and vendors were sprinkled throughout every available space of sidewalk or doorstep. We popped into a local cafe and split a banana mango smoothie for $2, rested on the balcony, and surveyed the bustle of the town below.

I had planned on exploring Musgrave Market for some local snacks and possibly last minute Christmas gifts, but we knew it was impossible to peruse without being incessantly hassled. I felt somewhat ashamed of the relief that I felt once we retreated to a quiet pub along the marina. I had mocked the advice that I had received about the “dangers of leaving the resort areas” in Jamaica, and here I was, seeking refuge, comfortably eating a veggie burger by a hotel's poolside bar along the water.

Many Port Antonio vendors were more aggressive than usual this past Saturday, but it wasn't entirely their fault. Port Antonio officials had allowed vendors to operate along the streets this year to make up for their extensive and ongoing roadwork, a project that was cited by many locals as costing them sales. Several sellers had complained about being confined to the market and struggling to even make a day's sale due to the seemingly never-ending construction.


As I mentioned, it's easy to spend money as tourists in Jamaica. Our meals ranged from $15 for delicious burgers and fries at Woody's Low Bridge Place to $150 for a several course meal at the Trident hotel.

I longed to experience the places where locals ate, but these places weren't always easy to find. For the second time, I felt a twinge of guilt for enjoying a decadent meal with other tourists, atop a hill overlooking the harbor at the Hotel Mockingbird Hill, high above everything that seemed to be The Real Jamaica.



We spent a lazy final day in Port Antonio at Boston Beach, snacking on grilled jerk chicken (not pictured), fried dumplings, bread fruit, and sweet potatoes ($24.50 for two meals). Lively with local surfers, children playing soccer, and warm air from the waves, I read until the sun sunk too low to continue seeing the words.


Ready for the numbers?

Flight – $111.70 (free flight on Southwest Airlines – paid taxes only)
Lodging – $585.00
Rental Car – $129.54
Rental Car Insurance – $42.00
Gas – $20.00 (estimate)
Food / Drinks / Entertainment / Miscellaneous – $336.25
Less: Barclay Points – $267.17 (estimate)

Estimated Total: $957.32


Clearly, we splurged on food and drinks. While it isn't necessary to dine at high-end places like the Trident Hotel, Bushbar at the Geejam, and Milles Fleurs at the Hotel Mockingbird Hill, I wouldn't necessarily expect to save much at your hotel restaurant. One breakfast at our hotel set us back $35 for a couple of omelets. After that, we picked up some fruit, coffee, and snacks from a local market for future breakfasts.

Even local spots charge tourist prices and renting a place to stay with a kitchen is pricey. We saved by avoiding all excursions and renting a car instead of hiring a driver. Plus, I didn't buy any souvenirs.

Readers: Do you enjoy visiting less touristy destinations? Where are your go-to vacation spots?

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Discussions — 9 Responses

  • Tonya@Budget and the Beach December 22, 2014 on 8:25 am

    Look like a lovely time and I enjoyed the pictures! I almost never skimp on food when I travel. It’s one of my favorite parts, but as far as staying in the not touristy versus touristy. I’m about 50/50. Just depends.

  • NZ Muse December 22, 2014 on 5:46 pm

    I know that feeling – like you can’t crack the surface and find those ‘local’ spots! Most memorably, in Prague perhaps.

  • Kassandra December 23, 2014 on 9:28 am

    I definitely love to visit places that most people wouldn’t immediately call to mind. I have yet to visit Jamaica (on my travel list). DH has been there many times and has seen the reality of the country (outside of the resort areas) and still finds it a beautiful place.

  • Melissa @ Sunburnt Saver December 23, 2014 on 8:21 pm

    I love your pictures!! What a totally awesome trip – Jamaica for less than $1000?? Awesome! And it sounds like you really enjoyed yourselves. I have to say, I can’t think of any off-the-beaten path trips I’ve taken recently. I’ve generally been so crunched for time, I stay in the cities and do the traditional ‘tourist stuff.’ In the past, when I had more time to plan, I did go on some pretty awesome off-the-beaten path trips. The Irish and Spanish countrysides were my favorite trips!

  • Amos December 23, 2014 on 10:39 pm

    Looks like you enjoyed your trip. Its fantastic that you were able to spend moderately in that trip. I am also in the mood of travelling off the town.

  • Alexis December 23, 2014 on 11:10 pm

    I’ve never been to Jamaica but I am loving these photos!

  • Myles Money December 24, 2014 on 2:50 pm

    It looks amazing and together with the free flights and cash-back points, it’s hard to imagine a better value dream holiday.

  • Allan December 26, 2014 on 3:29 pm

    Wow! Great pictures. 🙂 Here in Canada we have cold wind, dirty snow,grey sky and below zero temperature… oh well… I guess it’s time to shop around for a good deal in an all inclusive resort! 🙂

  • Michelle December 29, 2014 on 4:15 am

    Anthony Bourdain is my food and travel mentor. Love the pictures and I think we would be fantastic travel buddies!!


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