Born Thomas Wesley Pentz, Diplo fell in love with Jamaica about 20 years ago, specifically the parish of Portland on the northeast coast. “I was DJing on a cruise ship and got off at Ocho Rios and I passed through Port Antonio and got to Kingston,” says the 13-time Grammy nominee, who has collaborated with countless musicians, including Dua Lipa, Sturgill Simpson, Snoop Dogg, Shakira and Bad Bunny. “Portland is like Costa Rica, full of jungle and waterfalls. Port Antonio is a quaint little town that I kind of go to as a retreat,” Pentz adds. About eight years ago, he bought farmland and built a house there.
Pentz sees Port Antonio as a quieter option than Ocho Rios and Jamaica's other popular tourist destinations for those who enjoy nature, hiking, waterfalls and, of course, beaches. It also suits those looking for a more authentic experience. “This is a city where you can mingle with locals, and I think that's what's special about it,” Pentz said.
Born in Mississippi and raised in Florida, Pentz has traveled extensively as a DJ on every continent, including Antarctica, and a livestream of his DJ set from the Atlas Ocean Voyages World Voyager helipad was posted to YouTube in January.
Pentz recently became a runner, having run the Los Angeles Marathon and competed in the Malibu Triathlon, but he felt like there was something missing from the experience: a post-run celebration. So he started a 5K run series called Diplo's Run Club. The first ones will be held this fall in Seattle and San Francisco, with an after-party at the finish line that will close with a DJ set by Diplo and friends. When he's not running or traveling for work, he spends his time at his home in Jamaica.
Here are five of his favorite places in and around Port Antonio.
1. Geejam Hotel
When Pentz first came to Port Antonio, he would often hang out and work on music at GeeJam, a boutique hotel set in six acres of rainforest on the edge of the Caribbean Sea. “It was built as a kind of studio place for Kingston artists and singers,” Pentz said, and it still attracts artists, Hollywood stars, and Jamaicans from other parishes who check in for staycations. “You sometimes see Shawn Mendes and other artists recording in the studio,” Pentz said. Facing the white-sand beach of Frenchman's Cove, the hotel includes large villas, cozy cabins tucked away in the jungle, and a main building with 12 rooms. “It has a world-class vibe, but it also has a backpacker vibe at the same time. There's even a mushroom dispensary in the lobby,” Pentz added, noting that hallucinogens 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. Today, locals and tourists alike book rafting adventures that allow them to leisurely soak up the beauty of the island's flora and fauna. “The water isn't very deep, only about waist-deep, and you can swim a little wherever you like,” says Pentz. “What I like about this rafting trip is that along the way, we can stop at the beach and have some local food and Red Stripe for lunch at a great restaurant, Belinda's, and just chill out. Then we hop back on the raft and keep going.”
3. Vinyl Sunday at Natural Mystic Bar & Lounge
Natural Mystic Bar & Lounge is located in Port Antonio's Drapers neighborhood. “One night a week, an Italian guy and his wife and friends play records,” Pentz said of organizer Enrico Vicari. “They bring out old 45s and big speakers and it's like a dance-off, a big party in the street.” Pentz often stops by as a DJ when he's in town. “Portland has a lot of foreign residents, and on Sundays local families, Rastas and European tourists come to dance and listen to old-time reggae music. It goes on from sundown until about 2 a.m.”
“You can't get any more Jamaican than jerk chicken, and Piggy's is the best place in Port Antonio,” says Pentz. Newest Bond actor Daniel Craig would probably agree. During filming of No Time to Die, the cast and crew would often gather at this little restaurant in Market Square in the heart of Port Antonio. When the original restaurant burned down, Craig and his crew raised funds to rebuild. “It's a great place to eat good food and hang out with locals,” says Pentz. “I try to stop in at least once every time I'm in town.”
5. Boston Harbor
Considered the birthplace of the spicy jerk seasoning, Boston Bay is a city with a skate park, a beautiful bay, and one of Jamaica's few surf spots. It's also home to the Boston Jerk Center, a collection of outdoor food stalls specializing in jerk dishes. “There are about eight restaurants, some that do the best jerk pork and jerk chicken, some that do jerk vegetables,” Pentz says. Pentz recommends getting some takeout food and finding a spot to watch the surfers at Boston Beach. “You can also rent boards and take lessons. When I'm in town, I surf here.”
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