Diplo, born Thomas Wesley Pentz, fell in love with Jamaica, specifically its Portland parish on the northeast coast, nearly 20 years ago. “I DJed on a cruise ship, got off in Ocho Rios, and drove to Port Antonio to get to Kingston,” said multiple-Grammy nominee and winner who has collaborated with Dua Lipa, Sturgil Simpson, Snoop Dogg, Shakira, Bad Bunny and countless other musicians. “Portland is like Costa Rica, all jungle and waterfalls. And Port Antonio was this quaint little town where I would go on a sort of retreat, “Mr. added Pentz. About eight years ago he bought a farm and built a house there.
Mr. thinks Pentz, Port Antonio is a more relaxed option than Ocho Rios or other popular tourist spots in Jamaica for people who enjoy nature, hiking, waterfalls and, of course, beaches. It’s also for those looking for a more authentic experience. “It’s the kind of city where you mix with the locals, and I think that’s what’s special about it,” he said.
Born in Mississippi and raised in Florida, Mr. Pentz has traveled extensively and DJed on every continent, including Antarctica. A livestream his DJ set there, which took place on the helipad of Atlas Ocean Voyages’ World Voyager, was posted on YouTube in January.
Recently, Mr. Pentz became a runner. He ran the Los Angeles marathon and competed in the Malibu Triathlon, but found something missing from the experience: a post-run celebration. So, he launched Diplo’s Run Club, a series of 5K runs — the inaugural events will take place this fall in Seattle and San Francisco — culminating in afterparties, with DJ sets from Diplo and friends, at the finish line. When he is not running or traveling for work, he spends time at his home in Jamaica.
Here are five of his favorite spots in and around Port Antonio.
1. Geejam Hotel
When Mr. first arrived Pentz in Port Antonio, he often hangs out and works on music at Geez, a boutique hotel set on six acres of tropical rainforest on the edge of the Caribbean. “It was built as a kind of studio for Kingston artists and singers,” he says, and it continues to attract artists and Hollywood types, as well as Jamaicans from other parishes who checked in for staycations. “Sometimes you’ll see someone like Shawn Mendes or other artists who might be recording in the studio,” he said. The hotel, with access to Frenchman’s Cove, a white sand beach, has large villas, cozy cabins hidden in the jungle and a main building with a dozen rooms. “It’s like world class but has a backpacker vibe at the same time. There’s even a mushroom dispensary in the lobby,” he added, pointing out that psychedelics are not illegal on the island.
2. Rafting on the Rio Grande
On Jamaica’s longest river, the Rio Grande, bamboo rafts were once used to transport bananas from inland Portland to the coast for export. These days, locals and tourists book a rafting adventure for a fun way to soak up the beauty of the island’s flora and fauna. “The water is not very deep, it can be waist high, and you can go out wherever you want and swim a little bit,” Mr. Pentz said. “What I like about it is that halfway through the trip you stop at this beach and there’s an amazing restaurant, to Belinda, where you can get all the local food and a Red Stripe for lunch, and just hang out. Then get back on the raft and continue.”
3. Vinyl Sunday at Natural Mystic Bar & Lounge
Natural Mystic Bar & Lounge is in a neighborhood of Port Antonio called Drapers. “One night a week this Italian man and his wife and friends play records,” Mr. Pentz said, referring to organizer Enrico Vicari. “They brought out their old 45s and their big speakers and it was like a dance, a big street party.” Mr. often passes by. Pentz to DJ when he’s in town. “Many expats live in Portland and every Sunday there is a good mix of local families, Rastas and European tourists who come there to dance and listen to old school reggae music. It is from sunset to two in the morning.”
“You can’t eat anything more quintessentially Jamaican than jerk chicken — and to Piggy there is the best in Port Antonio,” said Mr. Pentz. Even the ultimate 007 himself, actor Daniel Craig, would probably agree. During the filming of “No Time to Die,” the cast and crew often hung out at this little eatery on Market Square in the heart of Port Antonio. When the original restaurant was destroyed in a fire, Mr. Craig and his friends raised funds to help rebuild this. “It’s a great place to eat some good food and hang out with the locals,” Mr. Pentz said. “I make sure to stop by at least once every time I’m in town.”
5. Boston Bay
Considered the birthplace of spicy jerk seasoning, Boston Bay is a town with a skate park and beautiful bay that is home to one of the only surf spots in Jamaica. It’s also a house Boston Jerk Center, a collection of open-air food stalls specializing in jerk cooking. “There are eight different restaurants and some serve the best jerk pork or jerk chicken, some have jerk vegetables,” said Mr. Pentz, who recommends grabbing your food and finding a spot on Boston Beach to watch the surfers. “You can rent a board and take a lesson. When I’m in town, I surf here.”
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