From Bob Marley and the unmistakable sounds of reggae to headline-making Olympians—the 1988 bobsled team and, more recently, Beijing games sprinting star Usain Bolt—Jamaica has earned more publicity for the Caribbean than any other island. For anyone seeking some real living culture along with their tropical beach getaway, Jamaica should be high on the list. The superlatively turquoise waters of the Caribbean may be else-where, at Turks and Caicos or the Caymans, but the seas and sand here are plenty clean for beach bums. Without a doubt, Jamaica has the most interesting and robust local flavor—complete with all the hang-loose, dread-locked Rastafarians you’re imagining—of any island in this fabled sea.
For the majority of visitors, especially first-timers, a trip to Jamaica means Montego Bay, which is fully equipped with glitzy hotels, clubs, and restaurants and even has its own airport, eliminating the need to fly to Kingston (130km/81 miles away by car). The megasize cruise ships spill out thousands of passengers here daily, encouraging touts to roam the beaches with pitches for watersports, reggae clubs, and pub crawls. With all that action, however, comes a citylike vibe: Mo’ Bay can feel a little hectic—not what everyone expects from a Caribbean beach holiday. But no trip to Jamaica is complete without a stop at Time N’ Place in Falmouth (just east of Montego Bay) for a daiquiri. Sure, it’s touristy, but the laid-back beach hut, where you can sip daiquiris and Red Stripes in hammocks, is an unforgettable, “I’m in Jamaica, mon!” experience.
Honeymooners and families often prefer the newer resort area of Negril, on Jamaica’s far western tip, for its romantic 7-Mile Beach and pampering all-inclusive resorts. Ocho Rios, almost due north of Kingston, is another significant resort area that offers a lot of natural beauty; “Ochie” is where you’ll find the famous Dunn’s River Falls, which cascades some 212m (696 ft.) to the sea. Near the eastern end of Jamaica, Port Antonio is more of an elite enclave and a still-untouched part of the island. Rafting trips on the island’s Rio Grande depart from here. For wildlife enthusiasts, boat “safaris” on the Black River (east of Negril, on the south coast) put you face to face with American crocodiles and one of the richest swamp ecosystems in the Caribbean.
Jamaica is a big island (11,396 sq. km/4,400 sq miles), and getting around it takes some time; so pick your base wisely depending on what sort of vibe you’re after. But no matter which area you choose, you’ll be surrounded by mellow Jamaican music and smiling locals bedecked in the green, red, and yellow of the country’s flag, and have no trouble finding fantastic little places to eat the delicious island cuisine. Jamaica’s well-established tourist infrastructure also means activities galore, from horseback riding on the beach to zip-lining in the forest to swimming with dolphins. Coffee beans are grown in the mist-shrouded mountains of eastern Jamaica; the famous brand Blue Mountain welcomes the public at its Mavis Bank facility for plantation visits and factory tours.
Venture away from the established resort spots, and you’ll discover Jamaica’s more authentic nooks and crannies, not all of which are savory: Poverty and crime are a problem on many parts of the island, and it pays to be a savvy traveler when visiting these areas. Kingston, for instance, on the southern coast and toward the eastern end of Jamaica, several hours from Montego Bay and Negril, is a vibrant city of 750,000 that may tempt you with its cultural offerings, but it’s best to keep your touring there to daytime hours and to go in a group. The South Coast of Jamaica remains largely undeveloped for tourism and offers plenty in the way of hidden treasures, but don’t expect it all to be well-scrubbed and hospitable. For better or worse, going off the beaten track is always going to involve some sketchiness, and that’s part of why you come—to see the real Jamaica, away from the resort bubble.