On the three and a half hour drive from Montego Bay to Portland parish in Jamaica, I had no idea what to expect. It was supposed to be lush - it is, after all, the countryside. It was supposed to be the most beautiful parish in all of Jamaica. I know what the Caribbean countryside looks like, and I know what people meant when they used the word "beautiful" to describe anywhere in the Caribbean - clear water in some shade of blue, soft sand in some shade of beige or black or pink or white, between one and a billion palm trees. Basically, anywhere in the Caribbean is considered beautiful with this standard of beauty - people simply describe the beach.
It was a last minute trip - a family issue brought me back to North America when I was supposed to be in Asia and afterwards, on a whim, I went to Jamaica for the long weekend. I hadn't done much research. I emailed three hotels to see if they had any availability, booked one, and sent a text message to a friend who has family in Port Antonio, Jamaica. That was it.
I especially did not expect that the community in Portland would be a big, extended family, and that the moment our driver picked us up at the airport, we would join that family. He became something of a big brother or older cousin to us - especially as he, half annoyed, waited an hour for us to get jerk chicken and steamed vegetables at Scotchies in Montego Bay before beginning the long journey to Portland. Upon arrival at Wilks Bay Resort, I still hadn't realized that I was part of a family. The owners, James and Mary, are gracious hosts. They welcomed us warmly and introduced us to our cook and housekeeper, and let us enjoy one last dinner in 2015 alone. They invited us to join a bonfire on the beach to bring in the New Year. We did not attend - instead electing to spend a quiet evening in the villa, drinking champagne and watching fireworks from the window.
But the next day, James and Mary became an aunt and uncle and the Portland ambassadors we didn't realize we would need throughout the duration of our trip. The hotels in Portland are private with large, unwelcoming gates and security that makes them difficult to see from the road and impossible to enter without a reservation. With the number of celebrities that travel to Portland, this obsession with privacy makes sense. Twice, we went to the Trident Hotel for drinks, which would have been impossible had James not escorted us. During the day, we were given the name of a knowledgeable guide to request for our hike through Reach Falls. Another night, we received a personal tour of the music studio at GeeJam and spent the evening with creatives of varying degree of celebrity. This too would have been impossible without an introduction from James.
The one thing we did outside of James' close watch was go to Boston, a neighboring town, for jerk fish and lobster. Afterwards, when we were told that our mediocre meal would cost more than every other meal we had in Jamaica combined, we knew we had been ripped off. We told James. We should have told him, he said. There was a jerk hut just two doors down from the one we went to with better jerk at better prices. We won't make that mistake again. As we packed our things to go after four days in Jamaica, James, Mary and a host of resort staff stood outside the villa waiting to send us off. We collapsed into five minutes of hugs and well wishes as they put pillows in the van for us to nap on the return trip to Montego Bay.
More tips and tricks are available on Portland Itinerary.