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  • Jamaica
    You haven’t quite experienced the most authentic Reggae concert in Jamaica until you’ve been to Rebel Salute. While Sumfest gets all the press and is more commercialized, Rebel Salute—held every January—is Jamaica’s largest strictly-Reggae all-night show, headlining every single big Reggae music name you can think of. Now held on the north coast, on the picturesque grounds of Grizzly’s Plantation Cove, this well organized, alcohol-free event welcomes everyone from families to couples. Camp out by bringing your lawn chairs and blankets to indulge in the best of Reggae all night long, under the starry nights of the south. Food and soft drink vendors are present, of course, as are souvenir sellers. Tour operators do arrange group round trips to the event—inquire with Clive’s Transport--and hotels near the venue offer deals.
  • Carretetera Al Naval
    Buda Bar, on the other side of the Havana tunnel in Cabaña, is a meditation center by day and a bumping party by night. Go after 10PM from Friday to Sunday to hear anything but reggaeton, play domino, or get your future told by an Osho card reader underneath the trees. Ask a young local for directions, as the spot is somewhat secret!
  • Negril, Jamaica
    Bourbon Beach, a popular beachfront music venue on Negril’s Seven Mile Beach, hosts local bands, reggae artists, or themed parties on an almost-nightly basis, to the delight of tourists and locals. People-watching at Bourbon Beach is great, the drinks stiff, and you get to dance in the sand to live reggae in Jamaica. The music starts up around 10 p.m. and continues until 2 a.m. Upstairs, a wide-open deck is open for stargazing or getting away from the crowd. Cover charges are only collected on nights when a recording artist performs. Alfred’s, nearby, is another longstanding option, offering live local acts three times a week for a US$5 cover.
  • Belmont, Jamaica
    Peter Tosh, the reggae artist and cofounder of the Wailers, was born in the scenic coastal village of Belmont, and it’s here you’ll also find his tomb and memorial. Fans can visit Tosh’s burial site on sprawling property maintained by his surviving family as the Peter Tosh Estate. Stop by the grounds and chat with family members, who will tell you about the life of Tosh, one of the most popular Rastafarians in the world, and let you visit his grave in exchange for a donation. Die-hard reggae fans will want to include this stop on the way around the western coast.
  • Part dive bar under the palms, part reggae dance hall, and part DJ club. This is the place to come for a great night out with friends. All Pura Vida!
  • Norman Manley Boulevard, Negril, Jamaica
    The west coast of Jamaica doesn’t sleep. If it isn’t some daytime live tunes on the beach, or a street party in the wee hours, it’s the evening live Reggae available in multiple seafront venues. At night, the island takes on a different energy and everyone comes out to enjoy the fresh air and the tunes. Almost every other Jamaican seems to have a natural talent for music. It’s no wonder, then, that there are plenty of local acts to go around, often performing covers of Bob Marley, from MoBay to Negril. Recording artists also show up regularly--from Beenie Man to Beres Hammond. Along the highways and neighborhoods streets are the latest posters, flyers or billboards announcing upcoming live Reggae shows. When in doubt, head to Pier One in Montego Bay, or Alfred’s, Bourbon Beach and Jungle Nightclub in Negril. Better yet, ask the locals, who love their music. The sound of Reggae is never too far off.
  • B11, Jamaica
    Jamaica Jazz and Blues, held just outside Montego Bay, is one of the Caribbean’s most well-known festivals. It hosts some of Reggae’s top stars alongside a host of well known American artists--past performers include the likes of Gladys Knight, Celine Dion and Maroon 5. The three-night concert is not a strictly jazz affair, but it’s a great time and one of the most fabulous international events in Jamaica. The large stadium accommodates several VIP tents for those who pay to receive all-star treatment, hopping from one all-inclusive food and drink tent to another, sampling local dishes from top chefs during or after performances. Part of the festival also includes a shopping village, showcasing some of the best art and other handmade Jamaican crafts. The large space and manicured lawn makes it ideal for strolls while the music plays on.
  • Guavate, a section of Cayey better known as the Ruta del Lechon (“Pork Highway”), bursts into a rush of food-infused ecstasy every Friday and Saturday. People from all parts of the island come to watch someone roast a whole pig over the open fire before chopping it with a machete. Side dishes abound. I recommend sorrullos (corn sticks), bacalaitos (cod fritters), alcapurrias (fritters made of plantain dough and stuffed with meat), and rice with different types of beans. The blood sausage is not for me, but my father and boyfriend devour it every chance they get. Here in the mountains, shacks of all sizes let you pick your poison—beer, piña colada, or mojito (made from lime, mint leaves, rum, and sugar)—and drink to the beat of salsa and reggateon music. This creates the euphoric atmosphere for which Puerto Ricans are so famous. The cherry on top of the piña colada: Guavate lets you absorb the laughter, music, and food for a reasonable price. If you want the pig, but not the rambunctiousness, take your food to El Yunque National Forest and eat it by a waterfall (see my “Swimming Under a Hidden Waterfall” highlight). To find it, get on Luis A. Ferre Expressway, take the exit toward PR-184, and follow the signs for Guavate. You’ll start seeing pork soon after you take PR-184, but wait about fifteen minutes (until you’re around km 27) before you stop to get all the real action.
  • 1212 18th St NW, Washington, DC 20036, USA
    Once the home of Teddy Roosevelt, this two-story lounge has featured local and world-renowned DJs spinning house, electronic, and trip-hop since 1995, as well as live bands playing jazz, hip-hop, reggae, funk, samba, and Latin. Along with the beats, enjoy the chill, living-room-like ambience, stylish crowd, and strong drinks in a variety of spaces—the Deck Bar is a favorite summertime hangout.
  • PR-458, Aguadilla Pueblo, Aguadilla 00603, Puerto Rico
    One of my favorite dive sites on the west coast of Puerto Rico is Crashboat in Aguadilla. This shore dive is easily accessible for all levels of diving, and you’re guaranteed to see something amazing on this artificial structure. Crashboat is named for this once Air Force based marina, where the “crashboats” would deploy to retrieve the crashed planes from training sessions of Air Force pilots. It was later abandoned and turned into a recreational area for locals and dive enthusiasts. Scout the pilings for seahorses, frogfish, octopi, and lionfish. At maximum depth of 30 feet, find a sunken base where bigger fish like to hide. Bring your flashlight to scope out the interior. Not a diver? No problem. Enjoy the sandy beaches, reggaeton music, and aromas of delicious Puerto Rican food all day long. One entire side of this recreational park is lined with street vendors selling food, handicrafts, and drinks. Want that true Puerto Rican vibe? Want to see how the locals relax on a weekend? Crashboat is your place. But if you’re not interested in the crowds, come here in the morning on a weekday. I dive here regularly, and I avoid crowds by diving early. Enjoy!
  • A4, Bull Bay, Jamaica
    If you’re staying on the east coast or close to Kingston, Wickie Wackie Live! is the place to be for some live reggae on the beach. For just a small entry fee, you’ll get to enjoy excellent local performances seaside—often held on Saturday evenings, 8 p.m. until midnight. There are onsite food and trinket vendors, as always, and the atmosphere is one fit for a wide audience, including families. Wickie Wackie is one of only a few live venues in Jamaica where up and coming artists get to show off their skills. Many made their debut here before rising to stardom.
  • Whithorn, Jamaica
    Aqua Nature Park, a well-maintained and verdant retreat 40 miles east of Negril, offers visitors a chance to take a dip and cool off in the Venture River. The river, which flows through a swimming hole on the property, has small, colorful fish and a cascade. Owner Steven delights in conducting walking tours of his family’s property, and can teach you quite a bit about the Jamaican plants and fruits he grows. (Don’t miss seeing the enormous cotton tree.) A casual restaurant and bar, with some reggae playing in the background, rounds this experience out into a lovely, low-key afternoon escape for couples, families, or anyone looking for a taste of real Jamaica.
  • 6, 56 Hope Rd, Kingston, Jamaica
    Though few tourists venture to Kingston, the capital and hub on the eastern coast of Jamaica, music fans should make the day trip to visit Bob Marley’s former home, now a museum dedicated to Marley’s life and impact on the world. A guided tour of this museum takes about an hour and a half and includes a 20-minute video presentation. Even devoted reggae fans will likely learn more about Bob than they ever knew. Exhibits include multiple awards, guitars, and his bed with an engraved headboard depicting a lion.
  • West End Road, Negril
    Rick’s is probably the most touristy spot in all of Jamaica, but there’s a reason it’s listed in 1,000 Places to See Before You Die, so don’t miss experiencing it at least once. Get there around 4 p.m. to avoid the crush of tour bus traffic that happens closer to sunset, then order a couple of cocktails—Rick’s serves up a myriad of options—and stake your claim on a prime viewing spot for the sunset and cliff-diving. Local divers swing from trees and drop into the surf or plummet from the surrounding cliffs, some of which rise more than 30 feet above the sea. Even the occasional tourist will brave the jump into the water below. A reggae band adds to the animated vibe. Lest you feel like just another tourist sheep at the sunset very-happy hour, console yourself in knowing that locals enjoy it almost as much as visitors do.

  • No visit to Antigua is complete without taking in the sunset atop Shirley Heights Lookout at its weekly Sunday sundowner party. The view from Shirley Heights is without a doubt the most famous, most photographed, most celebrated vista gracing Antigua. Immediately below, English and Falmouth Harbours clutch their bays. On clear days you can see Guadeloupe to the south and Montserrat with it’s still active volcano to the south west. It does get busy, so expect a crowd and while there might be a couple locals sprinkled in here and there, it’s mostly visitors. Around 7ish, the tunes crank up with either some reggae classics, some pumping soca, or even live a steelpan band. Smoke from a collection of barbecues compete with the music to fill the air and stimulate your senses. Expect chicken and ribs slathered in local flavors, plus burgers for the less adventurous. I did have some trouble getting grilled fish on my last visit, but once I found some, it was charred to perfection.