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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.

Watching the sun set on Jamaica‘s west coast is a bona fide activity. The island’s red skies are a sight to behold. I have yet to experience a better Caribbean sunset than in Jamaica. From Montego Bay all the way to Negril--famous for having the best--to Whitehouse, get your camera and Red Stripe ready for the last hours of daylight. You won’t lack for choice of seafront bars or scenic spots--from the trendy Pier One in Montego Bay to the wooden shack watering holes along Negril’s West End cliffs. Wherever you end up, there’s a very good chance you’ll get hooked on this daily sunset viewing routine.

An often overlooked fishing village located just 10 miles south of Negril, Little Bay’s small, crescent-shaped shores and white sands will tug at your inner beach bum. There are a couple of local guesthouse options in these parts, and not much else happening within walking distance—except a slice of daily Jamaican life and some sea activities such as kayaking and snorkeling off the nearby reef. Bob Marley loved Little Bay so much, he had a house here and wrote lyrics from this beach. It’s an easy day trip from Negril and a nice spot for shutterbugs.

The Caves, just west of Negril, is aptly named. While the 12 cottages and one villa sit atop honeycombed cliffs, the Blackwell Rum Bar, a private dining venue, and the massage table of the hotel’s Aveda Concept Spa are actually in underground grottos open to the sea. The setup is very Treasure Island, and the flicker of candlelight and the echo of waves off cave walls make it uniquely romantic. Each of the thatch-roofed cottages is as colorful as a paint box, and each gives a sense of being alone at the end of the land. This is one of music mogul Chris Blackwell’s Island Outpost properties, so the vibe at the Jacuzzi, sauna, or salt-water swimming pool is hip but relaxed. Although famed Seven Mile Beach begins almost where the cliffs end, the hotel itself has no beach, which is why a tradition at the Caves is to begin the day by jumping from the cliffs into the usually calm Caribbean below—or at least thinking about it.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

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.

Dining at one of Negril’s excellent cliffside restaurants is highly recommended, and the gorgeous setting of Ivan’s Bar & Restaurant at Catcha Falling Star makes it a very nice option. The longtime favorite has one of the best views along the coast and serves lobster dinners and classic Jamaican cuisine with a bit of a modern twist. Guests are seated under an open-sided thatched roof or out under the stars at private tables on a patio near the cliff’s edge. Another favorite choice for romantic cliffside dining is the restaurant at Rockhouse Hotel. (If you want more cocktails post-dinner, walk down to LTU Pub and mingle with the locals. Casual eateries and cliff bars along West End Road include 3 Dives and Sips & Bites.)

The hike up the Mayfield River to the waterfall nicknamed the Washing Machine requires walking in the river itself at times, and at one point, swimming through a tunnel. Along the way, you’ll be surrounded by lush fern trees and bamboo. You’ll need water shoes, a swimsuit, and a sense of adventure to take part in this, one of the best ways to see Jamaica‘s verdant interior. The trailhed is an hour’s drive from from Negril, and you’ll find lockers and a small restaurant there. Guides are always on hand to show you the way—you won’t make it without them, they know all the right places to place your foot. (Be generous with your tips—they may be having a great time, but this is their job.) The reward at the end of your hike? Two waterfalls. Swim underneath and feel the refreshing force of nature.

There’s a reason Blue Cave Castle (affectionately dubbed “BCC” by return visitors) has a following. Designed in the shape of a castle, it’s impossible to miss this dominating blue structure on Negril’s cliff side. Tower rooms offer dramatic views 50 feet above the sea, and yet surprisingly, rates start at $50 night and go up to only $120 for a stunning 2-floor “penthouse” suite on the top floor. Blue Cave is one of the West End’s best-kept secrets. Going to sleep in a castle to the immediate sound of crashing waves is a unique experience. Even if you don’t get to stay here, be sure to stop by the on-site Hideaway Eatery, owned and run by Chef Teddy, for a delicious lobster dinner.

Chill out from the sun at the Blue Hole Mineral Spring, a 50-foot deep turquoise natural pool sitting 20 feet below a cave opening. Jump off the cliff edge like the Jamaican divers on site, if you’re feeling brave. Otherwise, head down slowly on the ladder and let go from a closer distance (like I did). There’s a small entrance fee to this park--located about a half-hour drive south of Negril in the town of Brighton--which includes access to an on site bar and restaurant, as well as an outdoor traditional swimming pool. But my guess is you’ll be too tempted by the underground shimmering and therapeutic fresh water.

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.

Looking for some peace and quiet? No need to stay in the heart of Seven Mile. Keep walking all the way north of the beach--or hop in a taxi--and end up at Long Bay Beach Park. Past the hotel belt, this stretch offers respite from the chaotic tourist scene. There are picnic benches and changing rooms on site. Adjacent is an excellent beach restaurant, Cosmo’s, in case you have the munchies. Few folks venture here and you’ll be relieved to know that vendors stick to the busier, crowded stretch of Seven Mile. If you’re looking for even more quiet, take a taxi ride to Half Moon Beach, just 10 minutes away--a private, stunning crescent shaped stretch where you can swim and spend the day as long as you’re buying lunch at their excellent, casual on site restaurant serving the fresh catch of the day.

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.

Swimming and snorkeling around Xtabi (pronounced “X-tah-bee”) Resort’s underwater caves are a unique experience and a well-kept secret from first-timers. While it’s a great place to stay, overshadowed by places like Rockhouse Hotel, you don’t have to be a guest to enjoy this “meeting place of the Gods” as the name describes. You’ll want to have lunch at the casual, outdoor restaurant first--choices are excellent and include club sandwiches to jerk chicken (even if a tad pricier than from the street grills). After lunch and a rest, change into your swimwear and make your way carefully down the steps until you reach a sandy cove entrance into the sea, beside caves and jutting rocks. Splash in and come out on the front side of the cliffs, where there are ladders to exit or enter as well, if you’re feeling a bit timid. A laid back environment, gorgeous waters--just a tad more jade-colored on this end, for some reason--and underground caves ideal for photo ops make Xtabi a great spot to spend the afternoon. When you tire, climb back up to sip on a Dirty Banana and sunbathe on one of the platforms beside splashing waves.

See Jamaica’s natural beauty, from waterfalls to bioluminescent lagoons, enjoy spa treatments, and savor local cuisine with this five-day itinerary.