One Month in Jamaica

One month in Jamaica could mean four weeks of endless adventures, from beaches to museums and parties to festivals. Travel from lively Negril to lush Portland via Jamaica’s scenic north coast and fishing villages, before kicking back on the calm black sands of the south. The great thing about spending a whole month in Jamaica is that you have plenty of time to lounge on the beaches and to explore inland, so you get the best of all worlds.

Race Course, Oracabessa, Jamaica
Goldeneye, to be clear, is not an easy place to leave. The land—the former home of Ian Fleming, where he wrote each of the 14 James Bond thrillers that would cement his place in literary and cinematic history—sits next to the tiny town of Oracabessa, on the northern coast. A warm, blue-green lagoon curls from the ocean around a small island and then lets out into a bay. You can look one direction and see a jungle, then turn around and see pristine white sand.

Blackwell bought the property in 1976 as a vacation home and a space to entertain family and friends but later he decided to transform it. In 2016, Goldeneye debuted a jumble of new huts, arranged around a small cove, a short walk from Fleming’s house and the resort’s original villas. The huts vary in height, designed to capture cooling breezes and allow guests to forgo air conditioning. And, crucially, they’re much cheaper to book than the Villas. Which is key because, up until this point, if you wanted to plan a visit to Goldeneye, you needed to either know Blackwell personally or have the excess capital to shell out potentially five figures on a vacation. (Part of the resort’s enduring gravitational pull is that many of the celebrity guests check both boxes.) With the beach huts, Blackwell has expanded, once again, the ambition of his famous resort.
Port Antonio, Jamaica
This tiny hideaway overlooking the sea near Port Antonio originally served as a live-in recording studio for performers such as No Doubt, Alicia Keys, and Amy Winehouse. Although recording sessions still go on, Geejam is now a seven-room hotel, its guests often honeymooning couples acting out fantasies having nothing to do with rock and roll. Geejam’s cabins, especially, are very private, and guests sometimes spend days taking meals on their veranda and splashing in their outdoor Jacuzzi without being seen by anyone but the staff, who appear only when called. Of course, who wants to stay hidden forever when the Bushbar restaurant promises convivial chitchat, an occasional game of pool, and even live music? Not to mention that the hotel beach, in a cove across a road at the bottom of the property, promises four-poster sunbeds and, yes, Wi-Fi.
Negril, Jamaica
A signature experience in Negril is to go on a two-hour glass-bottom boat snorkel trip, toward the cliffside or to the nearby reef around Booby Cay. Truth be told, snorkeling isn’t a must if you’re not up for it—but floating on a small boat amid deep jade and turquoise waters and being able to see marine life 20 feet or more below through the glass is a memorable experience. If you do want to snorkel, the cliffside has stunning limestone formations and underwater caves, while the reef is filled with all sorts of marine life, from stingrays to barracuda. A glass-bottom boat ride shouldn’t cost you more than US$20 per person. Look out for Famous Vincent‘s boat—the best pick—or approach one you see resting along Seven Mile Beach, across any reputable resort. The boats—including Famous Vincent—occasionally ride along the cliffside resorts in the mornings or afternoons, looking for anyone interested in an impromptu adventure.
Norman Manley Blvd, Negril, 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.
Runaway Bay, Jamaica
A stone’s throw from the gated all-inclusive resorts in the Runaway Bay area is a public beach known as “Flavours,” named after the on site restaurant and bar. This beach has a lovely laid back vibe and is perfectly safe. Neighboring residents, families and those on a highway pit stop come here to relax during the day. Beware of the occasional hustler trying to sell you “ganja” and just politely refuse. Aside from a beautiful, long white sand beach, there are picnic benches and shaded seating areas where you can mingle and watch the world go by. Sample some authentic jerk and other local dishes from the restaurant and shoot the breeze while you soak up an authentic Jamaican beach town scene.
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.
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.
Duncans Main Rd, Duncans, Jamaica
Few visitors venture to Duncans Bay, a small town in northern Jamaica, halfway between Montego Bay and Ocho Rios. But its public beach, called Fisherman’s, is one of the best for a local vibe. The scenery is straight out of an old Caribbean postcard: kids play in the distance, colorful fishermen canoes rest on shore, and a ramshackle bar along the wide golden sands attracts the usual neighbors. Show up mid-afternoon, when the grill and some background music get started, while the waves splash and the sun prepares to set. The slow rhythm of this area, away from the resorts, vendors, and tourist trails, will make you want to stay for hours. No problem—there are local guesthouses a stone’s throw away.
Manchioneal, Jamaica
Reach Falls is an off-the-beaten-path delight. Located up in the John Crow Mountains on Jamaica’s east coast, this 30-foot jade-colored cascade tumbles into several pools in the surrounding rain forest. You’ll need a bathing suit and a waterproof camera to capture the natural splendor. Local guides are available to help you make your way across the swimming holes and levels, and show you the best spots. Or you can explore it solo. Because of its distance from tourism spots, there are no crowds, no harassment, just an entrance fee to your very own Garden of Eden. On-site changing rooms are available as you exit by the parking lot. Small fun fact: The falls play a minor role in the 1988 Tom Cruise movie Cocktail.

Somerset Falls, P.O.,, Hope Bay, Jamaica
There’s no shortage of refreshing waterfalls in eastern Jamaica. But after Reach Falls, I’d say Somerset—also located on the east coast—is a close second in natural beauty. Somerset Falls’ cascades can be reached by hiking or by canoe ride along the river. Either way, it’s a stunning, still relatively verdant area teeming with bird life—resident parrots—and caves to explore. It’s easy to find too, ideal for a day trip from either Port Antonio or Ocho Rios. Look out for a billboard right off the paved northern highway, about an hour and a half north of Ocho Rios.
Salt Spring Junction, Jamaica
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.
Calabash Bay P A, Treasure Beach, St Elizabeth 00000, Jamaica
Green might be a buzzword for some, but it’s the rootstock of Jake’s, the 49-room Bohemian hideaway on Jamaica’s Treasure Beach. Sprung from the fertile imagination of owner-artist Sally Henzell and established as a restaurant in 1991, Jake’s has gradually expanded. Now you can spend the night in quirky cottages where seashell-and-rock walls assure privacy in outdoor showers, recycled bottles simulate stained glass, and twig awnings provide shade. Henzell and her family have always been good neighbors, contributing to the construction of local classrooms and establishing a sports park. Now, monthly full-moon harvest dinners bring guests to a nearby family farm for locavore meals in the most delicious expression of the resort’s community values. From $95. (877) 526-2428, jakeshotel.com. This story appeared in the November/December 2011 issue.
Black River, Jamaica
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.
Frenchman's Cove beach, Jamaica
Frenchman’s Cove is more than a beach. It’s an idyllic escape. After paying a small entrance fee—used to preserve the grounds—you’ll hike about five minutes through verdant gardens flanked by an emerald river stream, before the views open onto a glorious beach and the Caribbean Sea. This cove was once a favorite romantic escape for Elizabeth Taylor and Burt Reynolds, and it’s not hard to see why. When you tire of the beach and waves, hop over to the river and swing from the vines into the fresh water. It’s an ideal spot to spend the day, for couples or for families.
A3, Ocho Rios, Jamaica
One of the most romantic drives in Jamaica takes you just outside Ocho Rios and onto the A3 highway, through “Fern Gully": a stunning three-mile gorge surrounded by sky-scraping, 30-foot fern trees. You’ll feel as if you’re on a completely different island as you pass through this natural, green tunnel, once a riverbed. Pull off to the side where possible to stop and take in the views, and even a walk. Because this is a road often taken by visitors and is one of Jamaica’s natural wonders, there are vendors lining up the road, but not so many that it spoils the view. Keep an eye on the road at all times—there might be a man on leaf-adorned stilts appearing before you. Never a dull moment in Jamaica.
Discovery Bay, Jamaica
Directly off the northern highway is Columbus Park, overlooking the scenic harbor at Discovery Bay, where Columbus was thought to have first anchored—although recent indications are that he sailed there from St. Ann’s Bay. The park is the only open-air museum in Jamaica, displaying artifacts dating back to Arawak times. Take in the glorious views, ideal for a photo op, and step back into a slice of Jamaica’s history.
Few venture this far east in Jamaica, but those who do will find one of the most authentic sides of the island, and the most secluded of getaways. A charming fishing village about thirty minutes past Port Antonio, Long Bay is as peaceful and scenic as it gets, with just a handful of affordable, casual guesthouses perched atop dramatic cliffs and overlooking a long stretch of deserted beach. No frills here, just nature and culture. The fresh ocean air, the roadside fresh seafood shacks and friendly locals will have you staying longer than you planned. Be sure to drive along the coastal highway and head as far as Manchioneal, another stunning fishing village that feels thousands of miles away from the touristy side of Jamaica.
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.
Negril, 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.

Fairy Hill, Jamaica
Located along a stretch of coastline that’s sometimes called the birthplace of jerk cuisine, the Boston Bay Jerk Center is hard to miss. Various meats are cook on open pits using a technique that may explain why jerk never tastes so good at home: Uncured pimento logs are placed over a bed of hot coals, and the meat is laid directly on the green logs. The whole operation is then covered up by a sheet of corrugated zinc and cooked until it’s black on the outside and tender underneath. You can place your order by the quarter, half, or full pound. Don’t forget to add jerk sauce, which you can also buy by the bottle as a souvenir.
Blue Mountains, Jamaica
Lush source of the mellow, world-famous Blue Mountain coffee, Jamaica’s longest mountain range is nature at its best, seemingly a world away from nearby bustling, noisy Kingston. In these mountains 7,400 feet above sea level, the air is cool, the views—of villages and falls across the mountains—are magnificent, and, yes, the peaks look blue. The winding narrow roads, though occasionally nerve-racking, add to the overall mystical atmosphere. A handful of hotels and cabins, including the prestigious Strawberry Hill, provide lodging. Staying in the mountains overnight is highly recommended so you can take the famous sunrise summit hike.
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