Top Caribbean Summer Festivals

Slap on the sunscreen and shimmy into your skimpiest swimwear for this Memorial Day Weekend bash, which bounces between the “happy island’s” Moomba Beach and the Renaissance Aruba resort’s pool. Headliners at the celebration of soul music, now in its 14th year, include Mr. Blurred Lines himself, Robin Thicke, Babyface, Ashanti, and old-school girl group SWV. Events kick off as early as 6 a.m. with live radio broadcasts; there are wet and wild beach parties and evening performances at the Soul Beach amphitheater, and the hijinx continue into the wee hours at various nightclubs. So come prepared to party.
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You’ll be tempted to stay put on one of this luxe but laid-back isle’s 33 spotless beaches, but Anguilla’s third annual “literary jollification” merits missing some shore time. Bookworms and budding writers gather for three days of reading, discussion and advice from a diverse group of authors, including 2014 Pulitzer Prize nominee Bob Shacochis (The Woman Who Lost Her Soul) and Richard Williams, father of tennis legends Venus and Serena and author of Black and White: The Way I See It. Magazine and book publishers will also be on hand to drop knowledge on fledgling scribes, and the schedule includes enough cocktail parties and sunset soirees to satisfy sociable scholars.
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Crowds descend upon Jamaica’s north coast, but Calabash offers a unique opportunity not only to mingle with such literary giants as Jamaica Kincaid, Salman Rushdie and Zadie Smith, but also to experience a cool, culturally authentic and little visited part of the island. Staged for a decade at Treasure Beach's boho-chic resort Jake’s, the “globalishus” gathering includes intimate author one-on-ones, open mike events and nightly jam sessions with local bands. Best of all: “Passion is the only price of entry.”
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Sample a wide musical spectrum on tiny St. Kitts, where this longstanding festival (18 years and counting) has featured soca, jazz, R&B, gospel and reggae. The lineup this year promises to be equally eclectic, with Trinidadian soca star Machel Montano, Chicago’s Bill Champlin, legendary reggae singer Freddie McGregor and merengue fusion artist Elvis Crespo already confirmed. Performances are in the evening, but savvy festivalgoers rock up to the stadium early, spread a blanket on the lawn and make a picnic of the tasty fare from the clutch of local food vendors.
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Make sure you bring or buy a “reggae bed” (a flattened cardboard box), because you’re gonna need to take a load off during Jamaica’s legendary reggae festival, known for late night revelry that continues way past sunrise. Now in its 21st year, the bass-driven Montego Bay bashment traditionally features local reggae and dancehall artists (Rohan Marley, Sean Paul, Buju Banton) alongside international stars (Mary J. Blige, Usher, Jay-Z), and this year The Voice season five winner Tessanne Chin will grace the stage in front of her home crowd.
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If it’s big names you want, it’s big names you’ll get at the fifth installment of this Dutch island’s soul, jazz, hip-hop and R&B festival, which will include acts such as Bruno Mars, Chaka Khan, Dianne Reeves, Nile Rodgers and Chic, and Juan Luis Guerra on three stages. This is one of the Caribbean’s priciest music fests, but with such star wattage, Sea Jazz offers plenty of bang for your buck. Just remember to pace yourself, as Curaçao’s crowds are famously gregarious, and the rollicking after parties and late night food truck pilgrimages are an essential part of the experience.
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“Little England’s” most popular festival dates from the 18th century, when the sugarcane plantations’ final harvest of the season would be heralded with music and merriment. Today the colonial-era celebration is a thoroughly modern mashup of raucous rum-fueled parties, craft markets and a children’s parade, culminating in a rollicking “road march” by scantily clad revelers through the streets of the capital, Bridgetown, on Kadooment Day (this year, August 4). With a similarly joyous vibe and equal amounts of soca and calypso, this is the summertime alternative to Trinidad’s carnival (the undisputed king of Caribbean fests).
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You’ve probably never heard of zouk, soukous, bouyon or cadence-lypso, but that can easily be remedied. For 18 years Dominica — a tiny and lush eastern Caribbean gem that’s not to be confused with the vastly different Dominican Republic — has been home to this celebration of music by Dominicans and other Creole-speaking folks that attracts standing-room-only stadium crowds. Go for the three-day event, but be sure to include extra time to enjoy the natural attractions (waterfalls, rivers, rain forest) and outdoorsy activities (hiking and diving) that are the island’s claim to fame.
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Fans of the meaty gastropod should book their tickets now to the TCI; the world’s only conch festival, fittingly, takes place on Providenciales, home to the world’s only commercial conch farm. “Conch-etitions” include spirited taste-offs between local and international chefs for the best conch chowder and conch salad, as well as conch-blowing and conch-knocking contests that are open to all. After sampling the fare, diehard conch cravers head to Da Conch Shack in the Blue Hills neighborhood to wash it all down with the beachfront bar and restaurant’s signature shot, called (what else?) the Conch Knocker.
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This fest arguably started the whole Caribbean trend when it launched 22 years ago. Back then it was limited to jazz performances in the capital, Castries. Now it has evolved into a dozen-day islandwide celebration of local culture, fashion, art and all genres of music, headlined earlier this month by R&B crooners Maxwell and KEM, and Caribbean soca stars Alison Hinds and Kerwin Dubois. The main stage venue at Pigeon Island National Park, with shimmering water, a centuries-old fort and a cloudless sky as the backdrop, is one of the Caribbean’s best. Plane seats, hotel rooms and event tickets go fast, so mark your calendar now for next year.
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