Diplo, born Thomas Wesley Pentz, fell in love with Jamaica, particularly its Portland parish on the northeast coast, nearly 20 years ago. “I was D.J.ing on a cruise ship, got off in Ocho Rios, and drove through Port Antonio to get to Kingston,” said the multiple-Grammy nominee and winner who has collaborated with Dua Lipa, Sturgill Simpson, Snoop Dogg, Shakira, Bad Bunny and countless other musicians. “Portland is sort of like Costa Rica, all jungly and waterfalls. And Port Antonio is this quaint little town where I’d go on a sort of retreat, “Mr. Pentz added. About eight years ago he bought some farmland and built a house there.
Mr. Pentz thinks Port Antonio is a calmer option than Ocho Rios or other popular tourist spots on Jamaica for people who enjoy nature, hiking, waterfalls and, of course, beaches. It’s also for those who seek a more authentic experience. “It’s the sort of city where you’re mixing with the locals, and I think that’s what special about it,” he said.
Born in Mississippi and raised in Florida, Mr. Pentz has traveled extensively and D.J.ed on every continent, including Antarctica. A livestream of his D.J. set there, which took place on the helipad of Atlas Ocean Voyages’ World Voyager, was posted on YouTube in January.
Recently, Mr. Pentz has become a runner. He ran the Los Angeles marathon and competed in the Malibu Triathlon, but found that something was missing from the experience: a post-run celebration. So, he launched Diplo’s Run Club, a series of 5K runs — the inaugural events take place this fall in Seattle and San Francisco — culminating in afterparties, with D.J. sets from Diplo and friends, at the finish line. When he’s not running or traveling for work, he spends time at his home in Jamaica.
Here are five of his favorite places in and around Port Antonio.
1. Geejam Hotel
When Mr. Pentz first started coming to Port Antonio, he would often hang out and work on music at Geejam, a boutique hotel set on six acres of tropical rainforest at the edge of the Caribbean. “It was built as a sort of studio for Kingston artists and singers,” he said, and it continues to attract artists and Hollywood types, as well as Jamaicans from other parishes who check in for staycations. “You’ll sometimes see someone like Shawn Mendes or other artists who might be recording in the studio,” he said. The hotel, which has access to Frenchman’s Cove, a white sand beach, has large villas, cozy cabins tucked into the jungle and a main building with a dozen rooms. “It feels 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 the interior of Portland to the coast for export. These days, locals and tourists alike book a rafting adventure for a leisurely way to soak in the beauty of the island’s flora and fauna. “The water’s not very deep, maybe waist high, and you can get out anywhere you want and swim a little,” said Mr. Pentz. “What I love about it is that halfway through the ride you stop at this beach and there’s an amazing restaurant, Belinda’s, where you can get all these local dishes and a Red Stripe for lunch, and just hang out. Then you get back on the raft and keep going.”
3. Vinyl Sundays at Natural Mystic Bar & Lounge
Natural Mystic Bar & Lounge is in a neighborhood of Port Antonio called Drapers. “One night a week this Italian guy and his wife and friends play records,” said Mr. Pentz, referring to the organizer Enrico Vicari. “They bring out their old 45s and their big speakers and it’s like a dance off, a big party in the street.” Mr. Pentz often stops by to D.J. when he’s in town. “A lot of expats live in Portland and on Sundays there’s a nice mix of local families, Rastas and European tourists who go there to dance and listen to old school reggae music. It goes from sunset until around two in the morning.”
“You can’t eat anything more quintessentially Jamaican than jerk chicken — and Piggy’s has the best in Port Antonio,” said Mr. Pentz. Even the most recent 007 himself, the actor Daniel Craig, would probably agree. During the filming of “No Time to Die,” the cast and crew would often hang out at this tiny eatery in Market Square in the center of Port Antonio. When the original restaurant burned in a fire, Mr. Craig and his pals raised funds to help rebuild it. “It’s a great place to eat some delicious food and hang out with the locals,” said Mr. Pentz. “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 pretty bay that is home to one of the only surf spots in Jamaica. It’s also home to Boston Jerk Center, a collection of open-air food stalls that specialize in jerk cooking. “There’s maybe eight different restaurants and some serve the best jerk pork or jerk chicken, some have jerk vegetables,” said Mr. Pentz, who recommends getting your food to go and finding a spot at Boston Beach to watch the surfers. “You can rent a board and take a lesson. When I’m in town, this is where I surf.”
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