One Week in Jamaica

Negril, or the “Capital of Casual” as it’s known in Jamaica, is everyone’s favorite getaway, from locals to the visitors who return year after year. The buzz of activity on Seven Mile Beach’s powdery white sands is tempered by the breathtaking, serene views of the West End’s cliffs towering over the Caribbean. Lots of bars, hotels, and restaurants line Seven Mile Beach, and local eateries and smaller boutique resorts are perched up on the cliffs. While there’s more hustle and bustle and throngs of tourists on this end of Jamaica, the region still offers many secluded spots and unique experiences.

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.

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.

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.

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.)

Bypass the roadside watering holes and take a boat ride to Floyd’s Pelican Bar, instead. This thatched hut stands on stilts out in the water, making it a dreamy spot for an afternoon of swimming and shooting the breeze, solo or with friends. It’s 30 minutes from Treasure Beach (arrange a boat ride through your guesthouse or resort), and you can arrive for lunch and stay until after sundown for the just-caught fish, rum, and chilled Red Stripe on the menu. Inside the tiny shack, the flags of various countries hang and previous customers have left messages scrawled on planks and benches. Sit outside and watch the pelicans flying in formation across the horizon.

If you’ve ever longed for a ride down a river to spot crocodiles—and who among us hasn’t? [editor’s note: me!]—you can do just that on the Black River in southern Jamaica. The river cruises are a popular tourist attraction, but they never feel overrun. Enjoy an hour-long cruise past tall mangroves and ferns, spotting tropical birds and stopping when the guides greet crocodiles. The enormous reptiles swim right up and even open their jaws while passengers cringe and wonder if the guide’s hand is about to disappear. Don’t miss this fun chance to see some of Jamaica’s wildest interior.

Going to dinner at Little Ochie is as fun as it is delicious. Pick your dinner—from a cooler of freshly caught fish—by species and by weight, then pick the style in which you’d like it cooked: jerk, grilled, escoveitch, and more. Pick a side of bammy, a thick round of cassava bread, to go with it. Your next decision is where to eat—head outside and choose a picnic table under one of the thatched huts carved in the shape of a fisherman’s canoe. The combination of beachy atmosphere and great fish makes this relaxed yet lively slice of Jamaica well worth the hour-long drive from Treasure Beach.

Just next door to crowded Doctor’s Cave Beach in Montego Bay is a quiet and spacious stretch known as Cornwall Beach. You won’t see more than a couple of people at a time here during the week. Late afternoons and weekends attract a few locals who come to relax and enjoy the restaurant and bar. A small entry fee—under US$5—covers the on-site facilities, including lounge chairs and snorkel gear. Cornwall Beach occasionally hosts a sunset beach party on Sunday afternoons with a “bottomless” Appleton mug option (that is, all-you-can-drink rum).

Pier 1’s greatest appeal is its setting: The open-air restaurant and nightclub occupies a pier that extends out into the Caribbean in Montego Bay. By day and into the early evening, the restaurant draws visitors and locals interested in a good meal with a stellar water view. At night, regular parties start late and run into the wee hours of the morning. Skip the noisy chain restaurant-bars down the street and try something more Jamaican, instead.

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.

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.

A delightful peach-colored villa set directly on Treasure Beach, this Jamaican-owned guesthouse is a gem, and feels more like a vacation home than a hotel. There are six spacious guest rooms and two larger suites, each with their own patios or balcony with a glorious sea view. The interior is intricately decorated with carefully chosen African-themed paintings and sculptures, and the owner—who returned after many years in the US—takes pride in providing true Jamaican hospitality. There’s a bar and no restaurant on site, but that doesn’t prevent the large kitchen and staff cook from taking your daily orders for breakfast and dinner, dishing out excellent local specialties that are served poolside with the sea in front of you. It’s one of my favorite places to stay and get away from it all.

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.