As close to heaven as you can get

Every time I visit Jamaica, I fall more in love with the place. The people, the culture, and the breathtaking scenery all come together to make every trip there an unforgettable one.

Of course Jamaica is revered for its sandy beaches and clear blue seas, but it is also well known for its Blue Mountains, where some of the best coffee in the world is grown. 

I took a business trip to Kingston a number of years ago, and was lucky enough to be taken to the Strawberry Hill resort for lunch one day. I confess that I’d had a bit of a late night the evening before, and so it was difficult to appreciate the sheer beauty of it all while nursing a headache. At least that amazing coffee helped. 

I vowed to return one day, and about a month ago, I got the chance. I’d always seen Cayman Airways advertising package deals to Strawberry Hill, but had never found the time to take advantage of them. In October I had a few days free in my calendar, and so my best friend Lynne Firth and I booked a two-night package that included a number of attractive extras. 

Getting there 

Early morning people will appreciate Cayman Airways’ scheduled flights to and from Kingston, as it means you can make the most of your time there, but I must admit that wheels-up at 7 a.m. was a bit brutal for me. Nevertheless, I rallied, and we checked in with time to spare. 

The flight to Kingston is only about 45 minutes, and you get a great bird’s-eye view of the 4,240 square-mile island through the windows before you land. We opted for ground transport booked through Strawberry Hill, which seems pretty expensive at US$90 one-way … until you’re on the route. The journey takes about an hour, and once you’re out of the town and heading up the mountain, you’ll grasp the benefit of having an experienced driver.

There are hundreds of curves, bends and zigzags in the road, with vehicles hurtling towards you at breakneck speed in a flurry of horn honks. I advise you to not check your phone, or try a game on your iPad through this drive. Even the hardiest soul will end up carsick. Besides, the view is so spectacular, you won’t want to miss a minute. 

From the moment we arrived at Strawberry Hill, the air just seemed fresher, cleaner and invigorating, which was a good thing, considering the amount of climbing we had ahead of us. The resort is built on the mountainside, which means lots and lots of stairs and steps. It’s beautiful, but tests your fitness levels. 

As we huffed and puffed behind staff members who almost seemed to skip up some impressive gradients, we felt guilty about those carrying our luggage to our cottage, 50 steps down from the main pathway. That guilt passed as our vision clouded. 

Strawberry Hill 

Strawberry Hill is one of a number of Island Outpost properties in Jamaica, joining GoldenEye, The Fleming Villa and The Caves, as a premier resort that regular features in Top Ten lists. Chris Blackwell, the founder of Island Records and Island Outpost is known to still visit his resorts on a pretty regular basis. He has signed many well-known musical artists to his label over the years, including the late, great Bob Marley, and references to his impressive career in the business can be seen throughout the cottages, main house, library and restaurant of Strawberry Hill. 

There is also a magnificent infinity pool on the property, immaculately kept gardens, perfect for private events, and an Aveda Spa where guests can relax and enjoy a menu of treatments that range from facials to massages and more. 

The resort enjoys the benefit of much cooler temperatures, due to its 3,000-foot elevation, and so none of the cottages are air-conditioned. You can just throw open the windows and enjoy the breezes. In fact, the beds have heaters for those chilly winter months. It’s a welcome break from the 90-plus degrees we swelter through in the summers in Cayman. 

Each cottage, without exception, offers incredible views of Kingston and the sea beyond, or neighboring mountains, and has its own unique name and vibe. We were staying in “Gong” – one of many references to Jamaica’s most famous native son, Bob Marley. Our cottage boasted an outdoor shower with wooden loungers, and a verandah off the main bedroom that looked out over lush vegetation and Kingston beyond. At nighttime, it was fascinating to see lights blanketing the capital, and dotted along the nearby mountainsides. 

We sat on the verandah of the restaurant each morning to have breakfast, including Jamaica’s national dish – ackee and saltfish (I can never get me enough of that stuff) and then worked out what we’d do for the day. Luckily, the package we’d purchased got us a spa treatment each, and a free tour of the Gordon Town Trail, so one day we went to the spa, and the next, we walked the trail. 

The Gordon Town Trail 

Since returning from our trip, I’ve spoken to a number of people who have visited Strawberry Hill, but did not walk the Gordon Town Trail when they were there. After walking it myself, I cannot emphasize enough that if you do nothing else, you need to book this tour. Now the property rated it as low difficulty hike, but I somewhat disagree, unless you have knees like accordions. You definitely need good shoes – sneakers or hiking boots – that can handle rocky, and sometimes slippery, terrain. 

Our tour guide, a rasta man named “Dave,” took us down from the resort to follow the tarmac road for a while, pointing out fruit trees as we gaped at the beautiful scenery of the valley. The air was so fresh and cool, and everyone we passed greeted us with a friendly smile. At that stage, we figured that it was all going to be a piece of cake – a leisurely stroll in the countryside, but on well-paved roads. That all changed as we entered the actual Gordon Town Trail. 

The trail takes about three hours to complete, and takes you along the Hope River, across bridges, and past amazing greenery, waterfalls, and small homes. It follows the old parochial trail, and many villagers of Gordon Town use it every day. When we walked it, we were passing schoolchildren and adults walking home, some with large bags of produce on their heads, as they expertly negotiated the rocky trail. 

It was kind of embarrassing to see us gingerly making our way over some of the more challenging areas, as we were smoothly overtaken by others wearing little more than flip-flops on their feet. Every passerby was cheery, exchanging pleasantries with Dave, and then continuing on their journey. 

I took as many photographs as I could without falling over, but no matter how many I took, I simply couldn’t capture the atmosphere and beauty of that trail. 

We were pretty tired by the end, but I am so glad we made the decision to do the hike. Besides, there was a signature Blackwell cocktail waiting for us back at Strawberry Hill – also included in our package, I might add. 

Final thoughts 

Jamaica is so close by, that many may not think of visiting there, choosing instead to travel to more exotic climes. Honestly, it is a magical place, and Strawberry Hill is somewhere that everyone should visit at least once before they die. We will definitely be returning. 


Following the river as we cross a bridge.


Our tour guide Dave teaches Lynne about coffee beans.


There are lots of small bars along the road, in c
ase the thirst overtakes you. – Photos: Vicki Wheaton


One of many stunningly beautiful vistas along the Gordon Town Trail. – Photo: Vicki Wheaton


A popular local swimming hole.


Strawberry Hill boasts an infinity pool that looks out over the capital of Kingston, 3,000 feet below. – Photos: Vicki Wheaton


The impeccably kept gardens of the Strawberry Hill resort are often used for weddings or yoga retreats.




Strawberry Hill boasts an infinity pool that looks out over the capital of Kingston, 3,000 feet below. – Photo: Joanna Lewis

If you value our service, if you have turned to us in the past few days or weeks for verified, factual updates, if you have watched our live streaming of press conferences or sent an article to a friend... please consider a donation. Quality local journalism was at risk before the coronavirus crisis. It is now deeply threatened. Even a small amount can go a long way to sustaining our mission of informing the public. We need our readers’ financial support now more than ever.