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Port Antonio: The Coolest Spot in Jamaica Right Now

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TravelPort Antonio: The Coolest Spot in Jamaica Right Now

While we heartily recommend soundtracking your whole summer with reggae, there's one thing music alone can't replicate: a pilgrimage to Jamaica. Port Antonio, to be specific, where you're worlds away from the cheesy resorts, and right in the thick of pristine private beaches and a decadent castle called The Trident.

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Jacket $1,750 by Bottega Veneta | Swim trunks, $275, by Isaia | Hat, $750, by Berluti | Sunglasses, $599, by Mykita | Necklace by Degs & Sal | Bracelet by Miansai

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Her dress by Nili Lotan | Necklaces throughout Dolce & Gabbana Fine Jewelry (cross) A.P.C. (octagon) | Bracelet by Hermès

When you announce a trip to Jamaica, the standard response is: Negril or Mo Bay? Here's your answer: neither.

Port Antonio, where Errol Flynn once hosted glamorous postwar bacchanalia for Hollywood starlets and the playboys who loved them, is a pristine swath of North Coast that couldn't be farther from the island's beer-chugging spring-break scene.

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Swim trunks, $220, Charlie by Matthew Zink | Her bathing suit by Peter Pilotto

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Left: Swim trunks, $255, by Isaia | Her bathing suit by Dolce & Gabbana

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There are a few legit spots to stay, but we like the Trident Hotel and the castle next door, which channels the nearby Flynn estate's bygone old-world grandeur. It's within striking distance of town, where you have to eat at least one lunch at Piggy's Jerk Centre, famous for the all-the-way-authentic jerk chicken. It's also a short drive from the epic private beach you see here, Frenchman's Cove ($10 entry fee). We promise no one there will try to sell you a damn Rasta Mon beanie.

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The evening is all about cocktails on the hotel veranda followed by sunset on the sweeping steps a couple of hundred yards downhill at the castle. For dinner, hit up Mike's Supper Club, where somebody will likely be playing jazz on the Ferrari red 1917 Steinway. For your Jamaican-music fix, check out Cristal Night Club, where the biggest records from Kingston get rewinds alongside Drake and Rihanna's dancehall homage “Work”; the Red Stripe, Guinness, and Red Bull are all flowing…and hey, if you can't find any good ganja, well, maybe you're on the wrong island.

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Shirt (blue) $580, by Gucci | Vintage jeans Levi’s | Sandals Barbara Shaum
Hat, vintage

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Starting Top Left: T-shirt, $195, by Burberry | Shorts, $510, by Louis Vuitton / Robe, hotel’s own / Her bathing suit by Dolce & Gabbana / Polo shirt $420 and suit (jacket in bag) $1,495, by Boglioli | Espadrilles, $195, by Ralph Lauren | Bag by Bottega Veneta | Watch by Piaget | Sunglasses by Mykita | Her top, pants, and belt Hermès Heels by Mansur Gavriel | Hat, vintage / White Shirt Louis Vuitton | Vintage jeans Levi’s / Her orange top Edun | Skirt
Adam Selman | Heels Mansur Gavriel

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Left: Blouse by Dries Van Noten | Hat by Berluti | Sunglasses by Mykita

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