Diplo, born Thomas Wesley Pentz, fell in love with Jamaica, particularly the parish of Portland on the northeast coast, nearly 20 years ago. “I DJed on a cruise ship, went down to Ocho Rios and drove to Port Antonio to get to Kingston,” said the 13-time Grammy nominee who has worked 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 is this quaint little town where I would sort of retreat, “Mr. Pence added. About eight years ago he bought some fields and built a house there.
Mr. Pentz believes Port Antonio is a quieter 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 town 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 DJ’d on every continent, including Antarctica. A live stream of his DJ set there, which took place on the helipad of Atlas Ocean Voyages’ World Voyager, was posted on YouTube in January.
Recently Mr. Pence became a runner. She ran the Los Angeles Marathon and participated 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 take place this fall in Seattle and San Francisco — culminating in afterparties, featuring DJ sets by 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 places in and around Port Antonio.
1. Hotel Geejam
When Mr. Pentz first started coming to Port Antonio, he often hung out and worked on music at Geejam, a boutique hotel set on six acres of rainforest on the edge of the Caribbean. “It was built as a kind 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 stays. “Sometimes you’ll 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 hidden in the jungle and a main building with twelve 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, noting that psychedelics are not illegal on the island.
2. Rafting 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 leisurely way to enjoy the beauty of the island’s flora and fauna. “The water’s not too deep, maybe in the middle and you can go out wherever you want and swim a bit,” Mr Pence said. “What I love is that halfway through 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 located in a Port Antonio neighborhood called Drapers. “One night a week this Italian with his wife and friends play records,” Mr. Pentz said, referring to organizer Enrico Vicari. “They bring out their old 45s and their big speakers and it’s like a dance, a big street party.” Mr. Pentz often DJs 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 get anything more quintessentially Jamaican than chicken – and Piggy’s has the best in Port Antonio,” Mr. Pence said. Even the most recent 007 himself, actor Daniel Craig, would probably agree. While filming No Time to Die, the cast and crew often hung out at this tiny restaurant on Market Square in downtown Port Antonio. When the original restaurant burned down in a fire, Mr. Craig and his friends raised money to help rebuild it. “It’s a great place to eat delicious food and hang out with the locals,” Mr Pence said. “I make sure to stop by at least once every time I’m in town.”
5. Boston Bay
Considered the birthplace of spicy spices, Boston Bay is a city with a skate park and a beautiful bay that is home to one of the only surfing spots in Jamaica. It’s also home to the Boston Jerk Centre, a collection of outdoor food stands specializing in jerk cooking. “There are maybe eight different restaurants, and some serve the best pork or chicken, some have vegetables,” said Mr. Pence, who recommends getting 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, this is where I surf.”
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