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First, despite what you may have heard, Jamaica isn’t for everyone. For all its natural beauty and laid-back rep as the birthplace of reggae music, the island is an economically beleaguered nation. To the majority of American and European tourists, it can look and feel very much like a so-called third-world country, with the local residents doing what they can to get by. If lushness and uninterrupted beauty are what you’re looking for, Hawaii might be a better bet.
There are two ways of experiencing the tourist destination of Negril: by mingling with the locals, or by signing up for the packaged tour. Sadly, it seems like the second option is the most popular, as the resorts that rule the Negril coastline—all-inclusive, corporate behemoths like Beaches, Sandals and Riu— offer little in terms of genuine out-of-country experiences.
 
The best way to see Negril is to avoid these places altogether, and to seek out spots like the Whistling Bird—a tiny and modest, family-owned-and-operated resort on the northern end of the beach. It’s far enough from the center of town to discourage visits from the pesky salesmen who work the beach—perhaps an odd attribute to point out at first, but an important one.
 
In Jamaica, those in need are generally too proud to beg, so they’ve perfected the art of the beach hustle. I’ve often thought that the jewelry vendors, jet-ski renters and drug dealers dotting the Negril beach could teach the rest of the world a thing or two about sales, and especially persistence. A couple walking the beach will almost always be approached, with each salesman routinely soliciting the man with a handshake before rather quickly getting down to business. Drugs might be the thing most peddled by the pushiest of salespeople, who will indeed get annoying— remember though, don’t lose your cool. Be firm, but not rude.
 
Ganja is everywhere in Jamaica, and its biggest dealers are probably cab drivers, bellhops and groundskeepers. Even though the plant is technically illegal, a huge percentage of people go to Jamaica knowing that they’ll be allowed to smoke in peace. The rule of thumb is to be discreet. Tourist dollars support Negril, so in general, police aren’t going to target spliff-smokers from abroad. Housekeeping staffs will even neatly organize your stash after straightening up your room, so tip accordingly.
 
Naturally, there’s nothing quite like a sumptuous meal and a relaxed atmosphere to accompany some fine herb. Back at the Whistling Bird, the menu offers gourmet dinners (have you ever had gourmet jerk chicken?) that you can order earlier in the day, while bonfires are lit at night on the weekend to set the mood. The fact that the Whistling Bird attracts its own talent is another plus. It’s not uncommon to find a Rasta quietly sitting at the bar with hand-carved cutlery, earrings and necklaces for sale, and they’re always worth the sometimes-high prices asked. By contrast, there’s rarely anything unique among the wares of Negril’s local art merchants, all of whom are generally selling the same stuff.
 
On the far end of the beach, where genuine pirates once roamed, the coast gives way to a cluster of small cliffs. Some of Negril’s best hotels are located here, most notably the Rock House—a rustic, cliff-top hotel with stellar food (go for the coconutcrusted chicken and especially the potatoes). Somewhat pricier than the disappointing hotels offered in Expedia’s Caribbean packages, the Rock House offers a once-in-a-lifetime experience as one of the greatest romantic vacation spots in Jamaica. Some have called it the island’s best hotel, with past guests including Bob Marley, Bob Dylan and the Rolling Stones.
 
Speaking of music, the best time to catch Jamaica’s big names is during the fall and winter, which is generally when the island’s best-known artists stay home and play for a revolving group of tourists. Two spots host the vast majority of live music in Negril: Alfred’s Ocean Palace and Bourbon Beach. The latter is the larger one, and has been the scene of live sets by the likes of Gregory Isaacs for just $10 U.S. Alfred’s offers a more intimate, club-style experience, with a smaller stage that’s frequented by such legends as Toots Hibbert and Yellowman. Both are on the water, giving patrons a chance to watch some of their favorite reggae stars with sand between their toes. Keep in mind that each place has a limited web presence, so you won’t know if someone is playing in town until you actually get to Negril. The colorful hand-painted signs stapled to telephone poles along the main drag of Norman Manley Boulevard will give you all the info you need—and all drivers can take you to either spot.
 
On that note, one of the highlights of any trip to Negril is the 90-minute drive from Sangster Airport in Montego Bay. You can catch a small prop plane that will take minutes, but for most people staying at the big hotels, their only chance to see Jamaica is on this drive. As soon as you pick up your bag, you’ll be accosted by sometimes surly drivers wanting your business. If they’re rude or offensive, ignore it—good times are near. The best thing to do is ask for a bus (not a van) whose windows aren’t tinted. This is the way to travel to Negril, even if it costs you an extra 20 bucks (for a total of about $80). The most reputable company is Kenny’s Tours, and it’s always preferable to contact them in advance to schedule such a trip. (On the down-low: drivers will be happy to make a ganja stop, and they also brake for beer and patties.)
 
Finally, if you arrive in Negril during the rainy season, don’t despair. Day or night, a Jamaican thunderstorm is a fleeting thing of beauty. Finding the best place to see one run its course is an adventure unto itself.
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