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Reggae, Roots & Luxury: Caribbean Music Festivals Paired With Plush Accommodations

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I love Caribbean music. No—really, really love it. To the point of fanaticism. And this fanaticism is what launched my travel-writing career. Over a decade ago, while penning pieces about reggae, soca, steelpan and more for a host of publications, I began fielding editorial requests to cover not just the music but the region and its luxury locales. The rest is history—a history that’s led me, blissfully, around the world with a notepad and a pair of perpetually wide-open eyes.

The moral of the story is that for me, culture and travel, art and wanderlust, have long gone hand in hand. So, too, have high-end and down-home. I love luxury just as I love local-ness. I’ve spend years writing about both because my journeys prove that they need not be mutually exclusive. And voila! From that conviction, a blog is born.

I thus launch my ForbesLife.com page with, fittingly, a post about how to enjoy two of my favorite things: Caribbean music and Caribbean luxury . Behold three local music festivals bearing my gold-seal stamp of approval, accompanied by three properties well worth resting your weary head in, after the music has stopped playing and the rum has stopped flowing and you’ve stopped moving your waist to that inexorable Caribbean beat.

WHERE: St. John, U.S. Virgin Islands

WHEN: January

ATTEND: Love City Live

This is the ultimate small-island-but-big-vibes extravaganza: a long weekend featuring a “Reggae Roadblock”—a D.J.’d street party—a sexy all-white beach fete, an all-day powerboat cruise to neighboring Jost Van Dyke and a climactic reggae concert featuring talented Virgin Island musicians. More than a few days of parties, more than a brand-name or a T-shirt slogan—it is all of those things, too—Love City Live is a family of like-minded folks, reuniting year after year in order to, as we say, “indulge in the vibe.” Come join our family. Experiencelovecitylive.com

STAY: Sea Shore Allure

It’s walking distance from Cruz Bay, which is as close to hustle-and-bustle as tiny, tranquil St. John gets. You’d never know it, though; this boutique property—14 one, two and three bedroom suites, each named for a different shell—feels secluded, serene and oh-so-sweetly off the beaten path. The décor is a perfect marriage of wood and stone, complete with Brazilian hardwood detailing, Travertine tiles, majestic four-poster beds and native stonework showcasing exceptional craftsmanship (yes, those are shells embedded in the majestic shower). The stunning penthouse suite has a spiral staircase and 360 views of neighboring St. Thomas, and the rooftop terrace beckons with a private hot tub (hint: it goes well with a glass of local Cruzan rum). Seashoreallure.com

WHERE: Montego Bay, Jamaica

WHEN: July

ATTEND: Reggae Sumfest

I must have lauded this event in over a dozen publications by now; how many more ways can I say that Reggae Sumfest is, quite simply, the be-all-and-end-all of reggae festivals?Since 1992 it’s attracted tens of thousands for stellar performances by the big names in Jamaican music, from Shabba Ranks to Beres Hammond and all the Marley sons. Three nights of shows, staged on an enormous field encircled by food and drink vendors, conclude well after the sun has come up. I mean well after—bring sunscreen for the closing set. By the end of the weekend, you’ll be amazed at your own stamina. And you’ll have earned an unofficial doctorate in reggae music. Reggaesumfest.com

STAY: Round Hill Hotel and Villas

Abovementioned stamina demands a plush place to rest your reggae-fied soul. Round Hill is that place. It’s a 110-acre boutique property featuring 27 luxury villas, 36 oceanfront rooms designed by Ralph Lauren, an infinity pool and pristine beach, exquisite organic dining—dishes like jerk chicken summer rolls, curry goat and butter curry lobster are locally sourced, with ingredients from the hotel’s divine organic garden—and a newly renovated spa whose “smoothie shots” of wheatgrass, spirulina, acai, goji and protein are the perfect antidote to the night before. Given its storied legacy—the onetime sugarcane plantation became a resort in the 1950s, hosting the likes of Sir Noel Coward and Oscar Hammerstein—Round Hill could easily sit back and rest on its laurels. Instead it keeps upgrading; the latest addition is a gleaming 2,300-square-foot fitness center with open courtyards and yoga pavilions. Roundhill.com

WHERE: Anguilla

WHEN: March

ATTEND: Moonsplash Music Festival

This fest is the perfect union of opposites. Upscale Anguilla—a British overseas territory seven miles north of St. Maarten, often considered the British St. Barts—meets intimate roots reggae at the Dune Preserve, which is practically is its own country: a funky beachfront bar intricately crafted from driftwood, open at all hours during Moonsplash. The audience is a motley crew—grown-up American hippies, Rastafarian locals, camera-toting tourists, Anguilla-loving celebrities (John Mayer and Kevin Bacon are fans)—and the shows are by classic reggae acts like the Wailers, Toots and the Maytals and Gregory Isaacs. Presiding over the whole thing is Bankie Banx, owner of the Dune and himself a reggae-rocker a la both famous Bobs: Marley and Dylan.

STAY: Cap Juluca

The first time I visited Anguilla, when the island’s tourism industry was taking off in the early 2000s, I enjoyed an otherworldly stay at Cap Juluca. It was one of the first luxury properties to open on the island, in 1988, and one glimpse of its gleaming white Greco-Moorish arches posing dramatically against the vivid blue sea had me instantly in love. That love has not waned. Maybe it’s the mile-long stretch of flawless beach. Or the 1,800-square-foot pool. Or the divine food options; Spice restaurant, now reopened as a Moroccan-style lounge, boasts plush silk couches, live music by the excellent reggae/soul artist Omalie360, and some of the best Anguillan crayfish I’ve ever consumed. Then again, maybe it’s just the all-around bliss and serenity in the air.Capjuluca.com