I hadn’t visited Puerto Rico since I was a teenager. I had come on a school trip as an Immaculate High student and didn’t remember much about the place. It was a short 2.5 hour flight from Fort Lauderdale (short because I’m blessed with the gift of being able to sleep through any flight), and though a hurricane had recently devastated a part of the island, the area I visited seemed fine. Tourism is the lifeblood of many of our islands, so while recovery efforts are important, so are the efforts to reinfuse commerce and industry.

American Black Film Festival

This trip was a media outing. I’m covering the Caribbean Hotel and Tourism Association (CHTA) Marketplace, where our Caribbean islands, their hotels, as well as various tour operators and service providers meet each other to solicit business and promote their destinations. 

On the drive from the airport to the hotel, the Hilton Caribe — literally the birthplace of the Pina Colada — I began to understand the personality of the island. Like the USVI, Puerto Rico is both part of the Caribbean and part of the United States. Like other Caribbean countries, it calls itself a rum capital. (We’ll enjoy the spoils while they figure out among themselves who actually holds titles). 

In San Juan, history meets modern, old meets new. I passed old buildings and forts situated beside towering high-rise buildings, all comfortably creating a textured backdrop of bustling Latin-Caribbean life. 

Diary of a Jamaican in Puerto Rico: Day 1
Modern structures of the city sit behind the ruins of an old fort in San Juan, Puerto Rico.

The surprising squawk of two large parrots greeted me in the palatial lobby of the Hilton Caribe Hotel. I was checked in and was off to my room in minutes. I walked by food and beverage options including old faithful, Starbucks, as well as an Italian spot. I could take a few steps down toward the pool and stop in the modern “Caribar,” where a custom metal sculpture sporting sinewy strands interwoven among themselves hung over the service area as its stunning centerpiece. Through the locked doors, I could see what seemed to be an infinity pool carrying my eyes across to the ocean beyond.

The decor was modern, with touches of sea shells and tropical colors here and there. The room was appointed similarly, with modern decor, stone counters, and a cool sliding barn door to the bathroom. From my sixth floor balcony overlooking the Caribbean Sea, I could see an old fort to my left. I had noticed another off the opposite side of the building when I alighted the elevator minutes before.

I’ve already made mental plans to go down and see if there are any canons I can visit before I leave. In the background, the ads playing between my YouTube videos are suddenly speaking to me en espanol, reminding me that I’m really not on home territory any more. I could have forgotten, since the view and the sound of the ocean so remind me of Jamaica.

I hopped on a shuttle over to a swooping, majestic convention Center with stunning architecture. In multiple spots, the “I heart PR” branding convinced me that I, too, loved Puerto Rico. 

After collecting my credentials and heading back to the hotel for a quick change, I came to what is known as the T-Mobile District, (Distrito T-Mobile), where a few hundred acquaintances danced, ate and drank as the red carpet was rolled out for delegates, exhibitors and media. Live entertainment, including choreographed dancers, singers and cultural ambassadors dressed in traditional attire put on a show to remember, welcoming us to the beautiful island of Puerto Rico. 

Diary of a Jamaican in Puerto Rico: Day 1
Distrito T-Mobile hosted the 3-day event’s welcoming gathering.

If this is day one, I’m really looking forward to what happens next!


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