Diplo, born Thomas Wesley Pentz, fell in love with Jamaica, particularly the Diocese of Portland on the northeast coast, almost 20 years ago. “I was DJing on a cruise ship, and after getting off at Ocho Rios, I went to Port Antonio and then on to Kingston.” The Grammy Award nominee and winner has collaborated with Dua Lipa, Sturgil Simpson, Snoop Dogg, Shakira, Bad Bunny, and countless other musicians. “Portland is similar to Costa Rica. It’s all jungle and waterfalls. And Port Antonio is a quaint little town that I would love to go to for some sort of getaway. Pentz has been added. About eight years ago he bought farmland and built a house there.
Mr. Pentz believes Port Antonio is a quieter choice than Ocho Rios or other popular tourist attractions in Jamaica for those who enjoy nature, hiking, waterfalls and beaches. It’s also for those who want a more authentic experience. “This is 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 and worked as a DJ on every continent, including Antarctica. A live stream of his DJ set from Atlas Ocean Voyages’ World Voyager heliport was posted to YouTube in January.
Mr. Pentz recently became a runner. He ran the Los Angeles Marathon and competed in the Malibu Triathlon, but realized there was something missing from those experiences. It was a celebration right after the run. So he started Diplo’s Run Club, a 5K running series. The first events will take place this fall in Seattle and San Francisco and will conclude with an after-party featuring a DJ set from Diplo and friends at the finish line. When I’m not running or traveling for work, I spend my time at home in Jamaica.
Here are five of his favorite places in and around Port Antonio.
1. Jizam Hotel
When Mr. Pentz first started coming to Port Antonio, he would often hang out and work on music at the Geejam, a boutique hotel located on six acres of rainforest on the edge of the Caribbean Sea. “It was built as a kind of studio for Kingston artists and singers,” he said. It continues to attract artists and Hollywood types, as well as Jamaicans from other parishes who check in for a staycation. “Sometimes you’ll see someone like Shawn Mendes or another artist recording in the studio,” he said. Open to the white sand beach of Frenchman’s Cove, the hotel features large villas, cozy cabins nestled in the jungle and a 12-room main building. “It has a world-class feel, but it also has a backpacker vibe. “There is also a mushroom vendor in the lobby,” he added, noting that hallucinogenic drugs are not illegal on the island.
2. Rio Grande River rafting
Jamaica’s longest river, the Rio Grande, once used bamboo rafts to transport bananas for export from inland Portland to the coast. Nowadays, both locals and tourists are booking rafting adventures as a leisurely way to enjoy the beauty of the island’s flora and fauna. “The water isn’t that deep, it’s about waist high, and you can go out and swim wherever you want,” Mr. Pentz said. “What I like is that you can take the bus and stop by this beach halfway through, stop by Belinda’s, a great restaurant, and try local cuisine and Red Stripe for lunch and just hang out. Then get back on the raft and keep going.”
3. Vinyl Sunday at Natural Mystic Bar & Lounge
Natural Mystic Bar & Lounge is located in a Port Antonio neighborhood called Drapers. “One night a week, this Italian guy and his wife and friends play records,” Pentz said, referring to organizer Enrico Vicari. “It seemed like they were having a big party on the street, dancing around with old 45s and big speakers.” When Mr. Pentz is in town, he often stops by to DJ. “A lot of expats live in Portland, and on Sundays local families, Rastas and European tourists go there to dance and listen to old-time reggae music. “From sunset until about 2 a.m.”
“You can’t get more quintessentially Jamaican food than jerk chicken. And Piggy’s is the best in Port Antonio,” Mr. Pentz said. Daniel Craig, the most recent 007 actor, would probably agree. While filming ‘No Time to Die,’ the cast and crew would often hang out at this small restaurant on Market Square in central Port Antonio. When the original restaurant burned down, Mr. Craig and his friends raised funds to help rebuild. “It’s a great place to eat good food and mingle with locals,” said Pentz. “I always stop by at least once every time I go to town.”
5. Boston Bay
Boston Bay, considered the birthplace of spicy jerk seasoning, is a city with a beautiful bay that is home to a skate park and one of Jamaica’s only surfing spots. There’s also the Boston Jerk Center, a collection of outdoor food stands specializing in jerk cuisine. “There are probably eight restaurants, and some serve the best jerk pork or jerk chicken, and some serve jerk vegetables,” Mr. Pentz said. Pentz recommends packing food and heading to Boston Beach to find a spot to watch the surfers. He said, “You can rent a board and take lessons. “I surf here when I’m in town.”
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