Jamaica. Exciting, provocative, colorful, unpredictable, and sometimes downright scary. If you habitually avoid the unexpected and seek the sanctuary of American food chains and a buttoned-down culture, then you’re better off in Florida. But if you live for adventure and spicy foods, this could become your favorite tropical getaway.

Jamaica’s rich history runs the gamut from pirates to plantations, from colonialism and slave revolts to proud independence. Today, the tropical island has become the land of relaxation, reggae and Rasta culture. Tourism now accounts for 45% of Jamaica’s (reported) foreign income, and I can see why. Thanks to the island’s warm, crystal blue water, teeming fish and gorgeous reefs, it is the perfect place to learn how to scuba dive or spend a relaxing day snorkeling. The adventurous can also go 4×4 off-roading through the jungle, take a river rafting trip to spot crocodiles, or hike to a secluded waterfall. If you can dream it up, you can do it here. From water skiing to Sea-Dooing to river tubing and horseback riding; it’s all available in Jamaica.

The minimum wage is only about $200 per month for full-time work, making it one of the poorest countries in the Caribbean. You might never notice the poverty if, like most vacationers, you travel directly from the airport to your hotel along the northern roads from Montego Bay to Ochos Rios, as this strip is lined with beautifully manicured golf courses and giant international-style resorts.

If you want to see the real Jamaica, you can rent a SUV (and make sure it has a spare tire, as the roads are filled with tire-popping potholes) at the airport and take a drive through the tropical mountains of central Jamaica, or tour the densely urbanized Kingston area, the resort-cluttered western coast, or the less-traveled lower portion of the island. Be careful, though, when driving at night, as goats and cattle roam not only the fields but also most of the roads, and it’s not uncommon to see animals get hit.

Planning a route in Jamaica is not a question of plugging point A and point B into Google Maps since what looks like a major road on a map is sometimes just a dirt track or, thanks to hurricane damage, doesn’t exist at all. Talk to the staff at your hotel before plotting out your journey.

Along the way, be sure to stop at some of the many roadside produce stands. The fruit they offer is wonderfully fresh and fragrant; there’s a world of difference in the flavour of the bananas and papayas at the supermarket back home and the ones you’ll be lucky enough to try here. Unless you’re a fan of food poisoning, avoid drinking tap water or eating meat and dairy in Jamaica. The jerk chicken or goat sold by roadside vendors is spicy, served with bread, and rolled up in foil, but can result in your vacation being spent in the bathroom, if you’re unlucky.

The Jamaican attitude is the epitome of the laid-back island lifestyle. Bob Marley and reggae rules, while the Rastafarian religion promotes smoking ganja for spiritual purposes.

A wise Jamaican told me the wistful story of a village fisherman who was visited one day by a stranger. The stranger told him that he could help him expand his business, and that in five years he could have ten boats, and in ten years he could sell his business and retire. He would have to work long and hard to build his fishing business into this empire, but its fruits would be plentiful. The fisherman responded simply, “Why would I want to do that, mon? I fish when I want to, sit around all day, smoke ganja and laugh with my friends. I already feel like I’m retired!”

If you’re looking for gorgeous beaches, this may not be the best destination for you, depending on where you’re staying. Jamaica has a culture of littering, and most of the beaches have so much litter that you almost can’t see the sand. No, really.

As you may have heard, for all its beauty and sensual pleasures, Jamaica is not the safest spot in the Caribbean. There are more than 1600 murders per year here, for a population of only 2.9 million. And, according to Amnesty International, more people are killed by police here (per capita) than anywhere else. Although marijuana and cocaine (two major Jamaican exports) are illegal, a great many people you meet in passing are eager to hook you up with your drug of choice. Leave your valuables at home because a quick peruse through TripAdvisor will enlighten you to just how many upscale hotel room robberies happen, and how vulnerable your in-room safe is to theft via master-key.

While most people are friendly and welcoming, it’s still advisable not to wander too far off the beaten path. It’s not unheard of for tourists to be shot at when they stumble upon a hidden marijuana crop. Growers are in a state of constant warfare with local authorities and the U.S. DEA, which operates here as well. We’re anything but shrinking violets, but we got a bit spooked after taking a detour in our rental car down a red dirt road and finding ourselves amid fields of marijuana bordering mansions the likes of which you’d be hard-pressed to match in Palm Beach or Beverly Hills.

Despite all the craziness that is Jamaica, it still tops many tourists’ lists for tropical vacation getaways. That’s thanks in part to the famously hip and exclusive group of Island Outpost resorts. Island Outpost owner Chris Blackwell used to own Island Records (Bob Marley, U2, The Cranberries, etc.), but sold the label to devote his attention to his resorts, which have become a magnet for well-heeled pop prodigies.

Other Essential Jamaican Adventures

While traveling in Jamaica, there are a few adventures that you should try not to miss.

A must-do adventure is the fascinating Jeep Safari Tour. Venture behind waterfalls and into swimming holes so secluded you can only reach them via the tour’s off-roading Range Rover. Lunch is provided, but make sure to request a plant-based meal in advance. You’ll also get to see 18th century ruins of a plantation that was destroyed during the famous slave rebellions.

One of the most popular attractions in the Ochos Rios area is Dunn’s River Falls. For an awesome experience, book a guide and you’ll be able to climb up the 600 feet of cascading waters. It’s not only a place for challenge, but extraordinary beauty. At the top of the falls, you’ll find a small village, food and shopping.

Across the street from Dunn’s River Falls is Dolphin Cove. It is here that you can touch, swim with, or even kiss dolphins. There is also a hair braiding booth and a beach grill. Feel free to interact with the cove’s remarkably friendly birds and explore their jungle haunts. It’s a great place to spend the day, or a couple of hours in nature.

If you enjoy Reggae music, don’t miss the Zion Bus Line Tour, complete with dreadlocked driver. This adventure will take you to the birth and final resting place of Bob Marley in the village of Nine Miles, as your guide shares stories about the area and how young Bob grew up.

If you like cycling, then check out the Blue Mountain Bicycle Tour, and take a ride through lush tropical rainforest and coffee plantations. Catch the trails on horseback with Chukka Cove Adventure Tours. Bring your bathing suit, sun block, and a towel and be prepared to ride your horses in the ocean. The ride is three hours and you’ll have the time of your life–we promise!

Good-to-know: Chikungunya fever (commonly known as Chik V) is a mosquito-borne virus on the rise throughout much of the Caribbean, including Jamaica. Though the effects are not deadly (fever, rash, joint soreness), they aren’t pleasant. Most hotel rooms should have mosquito nets, but not all do. So bring your own mosquito repellant, and apply liberally!

Next up: Reviews of Island Outpost’s three resorts, a scary situation, and the location where 007 was created.

James Bond is Alive at Goldeneye Resort in Jamaica

On a sandy hillock overlooking Jamaica’s northern coast, is a single-story white bungalow. Through its wide open windows you can feel the warm Caribbean breeze and hear the crystal blue water lapping at the shore. It is this 15-acre waterfront property now named ‘Goldeneye’, that inspired Ian Fleming to create his famous James Bond character.

Goldeneye is nothing if not inspiring. Its secluded beaches and private villas make you feel as though you’ve stumbled upon your own private paradise. No one could possibly dampen the blissful buzz that is created by the tropical greenery, plush surroundings, incredible cuisine and friendly people.

Although the property now has several villa areas, you can also opt to bring friends and stay in the “Fleming Villa“, the now-plush white bungalow where Ian Fleming wrote all thirteen James Bond novels–and where Sting wrote ‘Every Breath You Take’.

It’s surrounded by dense tropical vegetation and is completely private, which is perhaps part of the reason it has become a favorite of the likes of Johnny Depp, Jim Carrey, Harrison Ford, and Pierce Brosnan, not to mention supermodels Cindy Crawford, Kate Moss, Christy Turlington and Naomi Campbell.

It wasn’t always this way, though. In 1946, the consummate theatrical personality of his time, Noel Coward, was the first paying guest to stay at the property. He described it as being “a perfectly ghastly house, no hot water, pictures of snakes plastered all over the bedroom wall.” He referred to the place as “Golden eye, nose and throat”, but despite that called his stay “the happiest two months I ever spent.” Soon after, he built his own house just 10 miles away.

In the years since, Goldeneye has seen many of the most talented people of our time pass through its gates. Evelyn Waugh and Lucien Freud were frequent guests of Fleming’s wife Ann Rothermere; Donald Sutherland, Michael Caine, Katherine Hepburn, Errol Flynn, Sir Lawrence Olivier, Cecil Beaton, Sir John Gielgud, Mary Martin, and many other celebrities were all guests while the Flemings owned the property.

The day Truman Capote visited, Fleming exclaimed, “Can you imagine a more incongruous playmate for me?” British Prime Minister Sir Anthony Eden chilled here for three weeks, in the wake of the Suez crisis. He later wrote to Fleming, “I do not think that there is any other place anywhere that could have given me the rest I have to have. The bathing, the beach, the seclusion, the size of the grounds were all just perfect to enjoy and be concealed.”

Twelve years after Fleming’s death, Island Records founder Chris Blackwell talked Bob Marley into buying the property. “But then he got cold feet, said it was too posh, so the next year, when I was flush again, I bought it myself. The original for sale document said Bob Marley and we crossed that out and wrote in Chris Blackwell,” says Chris. It was Ian Fleming who recommended Chris for the job of location scout for the first James Bond movie, Dr. No in 1961, giving him his first job in the entertainment industry.

Island Records’ artist roster included U2, Bob Marley, Melissa Etheridge, Steve Winwood, Roxy Music, Robert Palmer, Grace Jones, and the Cranberries. Chris sold the label in 1989 to focus on his growing Island Outpost resort business, but the rock-star ethos is evident in all the properties, especially Goldeneye.

With outdoor showers, private media rooms stocked with James Bond boxed sets, and more premium booze than you could drink in ten vacations, each grouping of villas is the ultimate in tasteful hedonism.

Goldeneye’s main beach so private that we saw not another soul during our entire stay (and we visited the beach often). Its soft white sand and warm crystal waters are simply incomparable. If you’ve ever dreamt of the perfect beach-absolute privacy and serenity-but thought that it couldn’t exist in the real world, think again.

If the main beach is private, the villa areas are even more so. We stayed in our own private, gated area comprised of five cabanas and several large patio areas. Through the open doors and windows of each cabana is a breathtaking view of a private lagoon and sandy white beach. We could sleep in any of three bedrooms, raid our fully stocked kitchen, or hang out in the privacy of our posh media room / lounge villa, complete with big-screen TV and DVDs. We also had the choice of several inviting indoor and outdoor tubs and showers, stocked with locally-made fruit- and coconut-scented amenities.

Villa areas are connected by a series of narrow stone walkways, lush with tropical vegetation. They’ll also lead you to the white dining hut and patio, where the dining experience is as much like having a private chef as you’re likely to experience outside a rock star’s mansion or a prime minister’s official residence. The food is wonderfully fresh and tasty-and completely customisable, no matter what your dietary habits.

The dining patio has a fully stocked bar hut which is manned by a friendly bartender, who makes amazing fruity liquor concoctions, and who sports a silver, marijuana-leaf necklace. Although dinners are scheduled around the guests so that you will likely have the entire patio to yourself, it is also a delicious treat to have a white-linen table set up in the privacy of your villa area.

The food is as plentiful as it is delicious, and I found myself slipping the occasional scrap of meat to Stripey, and adorable though skinny, tabby kitten I bonded with during our stay at Goldeneye. Apparently, many celebrities have also taken a shine to Stripey and one or two have come close to kidnapping her and taking her home with them. I also had fun hurrying the two resident hens down the walkways–they were so amusingly un-Jamaican in their offended ill-humor.

If, while on vacation, you’ve ever felt you could spend all day in your room, you’ll surely feel it here. However, we strongly suggest that, as often as often as you can drag yourself away, you leave your villa sanctuary and explore all that Goldeneye has to offer, such as their selection of water sports and activities.

Simeon and Clifton will be happy to teach you how to sail or windsurf, or take you on a trip to any of the area’s many attractions. Simeon was kind enough to take us Sea-Dooing along the coast. The water in Jamaica is always perfectly warm, no matter how far you venture from shore.

As we jetted past several giant resorts and gazed at their crowded beaches from afar, we couldn’t help thinking how lucky we were to be guests at a fantasy get-away like Goldeneye.

The tropical greenery is balm to the chapped, northern soul, the plush surroundings are in perfect taste, the food is wonderful and the staff are friendly and accommodating. What else is there to say? It’s the kind of place 007 would have chosen for a little R&R.

Next up: Reviews of Island Outpost’s The Caves and the sometimes-scary Jake’s.

Jake’s is a Little Scary

If you seek a diversion from the tourist mainstream, you may want to escape the Americanized northern shore of Jamaica and immerse yourself in the bohemian feast of color (and culture) that is Jake’s — the Caribbean’s most Instagrammable resort.

Jake’s is a funky and eccentric getaway located in a secluded little fishing village called Treasure Beach, a half-day’s drive from both the Montego and Kingston airports. The southern side of the island is notably less tropical than the touristy northern coast, with lush greenery being replaced by rolling hills and close-cropped farmland. The edgy ambiance and focus on adventure at Jake’s has enticed the occasional celebrity guest–Joan Osborne, Lennox Lewis, and U2’s Adam Clayton–as well as photo teams from numerous fashion magazines.

Jake’s offers travelers the chance to experience laid-back seaside life in small, Casbah-style villas that are reminiscent of Morocco. Don’t expect your villa to be decked out with luxuries. Jake’s is all about the bohemian beachcomber lifestyle, and for that reason you won’t find a TV–or even a telephone–in your room. What you will find is Aveda shampoo, a CD player (bring your own discs), and an abundance of inspiration.

The complete lack of a gate or any sort of security (and no phone or safe in the room) — especially since all the surrounding houses have bars on their windows and barbed-wire fences — made us a bit nervous. That, coupled with the fact that waves hitting the rocks at what seems like 1000 decibels, and the 100+ feet between each villa, ensure that you not only have complete privacy, but also that nobody would hear us if we screamed. We weren’t oblivious to the abject poverty that surrounds Jake’s, and the reality that the locals see relatively wealthy tourists coming and going from Jake’s. What that added up to, we don’t know, and I doubt anyone local would talk about it, but I did find reports of robberies at Jake’s by digging around on the Interwebs.

From the rooftop patios on the gorgeous honeymoon suites, to walls inset with colored bottles, beads and conch shells, to the outdoor bathrooms with doors of tightly-tied twigs, this is one place you won’t soon (or ever) forget.

Jason Henzell, the owner, is legendary in these parts. During our stay, he was busy painting the nearby school–one of many local charity projects he has in the works. To say that he is highly regarded by both his colleagues and the locals would be an understatement. Jason was born on the island to father, Perry, who directed The Harder They Come, and mother, Sally, a former set-designer who designed most of the suites at Jake’s. The entertainment industry connections and lifestyle are evident in the unique look and feel of Jake’s. Sally Henzell originally bought the land, planning to make a vacation villa for family friends.

“My mother started Jake’s as a restaurant as there was nowhere to eat and then people started asking for rooms. My mother and I both share a love for Treasure Beach as my grandfather built a beach house, Treasure Cot, in 1941. [Treasure Cot was rented to Alex Haley to write Roots.] It’s where we spend family holidays,” says Jason.

Seeing the potential, Jason left banking to become a partner in the resort. He introduced a youthful, upbeat attitude by starting a tradition of bonfires and moonlight parties with appearances by local reggae bands.

“People see it as a melting pot for visitors and locals.”

Since then, Jake’s (named after a parrot of local renown) has blossomed to fifteen villas, but Jason assured us that he intends to keep it small, so as to not lose the authentic Jamaican feel of the place.

Fresh from visiting other resorts on the island, we were surprised to see just how integrated Jake’s is with the local area.

Most island resorts try hard to wall themselves off from the locals, but walking to the honeymoon suites from the check-in area at Jake’s, we heard a baby crying and noticed a local Jamaican mother and her children on the porch of their house right next to the pathway. If you’re charmed by the ambiance of colorful laundry dangling from the clothes line each time you pass, then Jake’s is your kind of place.

For many, a big part of the attraction of Jake’s is the opportunity to interact with locals at ‘Jack Sprat’ (where you can get great pizza and local Red Stripe beer) and get to know the local community. However, this opportunity also means that your stay will lack the security of fencing and a guarded gate, features of most upscale homes in the area and something which many travelers treat as de rigueur when holidaying in Jamaica. However, if you’re an adventure (or culture) – seeking traveler unphased by backpacking trips through Europe or Asia, then Jake’s may be your ideal Caribbean getaway.

If the lack of TV leaves you at loose ends (poor soul!), just track down Jason and have him arrange one of the enticing adventures that are available-river tours, bike trips, manatee watching and others. Oh, and be sure to bring a book or two, because there are few pleasures to match reading on the roof or porch of a honeymoon suite at Jake’s while the waves crash against the rocks below.

The food at Jake’s is simple but tasty, with a focus on seafood and American comfort foods such as pancakes and pasta. The cost of meals is not included with the room as it is at most other Island Outpost properties, but dining is quite inexpensive and is definitely the best you’ll find in the area. Be sure to order a fruit punch or an alcoholic concoction from Duggie, who mans the bar (and who may also have posted the sign that asks, “Why drink and drive when you can smoke and fly?”). Sip it slowly and watch the dolphins play and the sun set over the sea, as we did, one splendid evening at Jake’s.

Other notes:

– The official story is that Jake’s is after a famous parrot, however, in the local Jamaican dialect, “Jake” is another way of saying “white guy”.

– Stay away from the run-down three-bedroom cottage. The Honeymoon Suites (“Octopussy 1, 2 & 3”) are the nicest accommodations on the property.

– There is an archaic PC in the main building with an incredibly slow Internet connection from which you can check your email.

– The beach is covered with small (and some not-so-small) holes from which crabs continuously scurry to and from, and the pool is not the cleanest ever–so, if you’re looking for swimming, this is something to note. And if you come across a hustler on the beach, just tell him “Cho’ mon’. Don’ harrass da touris'”

Next up: Getting lost in The Caves.

Getting Lost in the Caves

When the likes of Harrison Ford, Scarlett Johansson, Bono and the Sports Illustrated swimsuit photographers visit Jamaica they head to The Caves. Down past the tourist-paved beachfront of Negril, at the quaint southern extremity of the resort area’s long stretch of sand and sea, is one of the most romantic getaways in the Caribbean… Think casual luxury with an on-site spa and delicious food whenever you’re hungry. The sound of the ocean from your bed. Privacy.

Still within reach of all the snowbird hotel resorts (but far enough removed that you may not notice), The Caves has easy access to all the nightlife and amenities that come with industry giants like Sandals, Beaches, and Hedonism (to which you can request a free day pass), but none of the package-deal feel. In fact, you will rarely notice other vacationers while visiting The Caves. This is partly because the resort has only ten villas, and partly because of the ingenious layout of the resort, which allows you to feel completely safe, secluded and relaxed no matter where on the grounds you happen to be.

If you’re looking for opulent luxury and Frette sheets, this isn’t the place for you. But if you’re looking for casual luxury and loads of charm, you’ve found your heaven!

The Caves is a truly unique retreat. It boasts ten acres of tropical jungle and seaside cliffs, with stone walkways leading guests through lush greenery to some of the most breathtaking sea caves in the Caribbean. These spectacular grottos were carved by eons of waves breaking against volcanic rock and they now allow guests to jump through gaping holes in the ground straight into the crystal-clear sea thirty feet below.

As you might imagine, this also makes for some amazing swimming, snorkeling and diving. We suggest you grab some snorkeling gear and embark on a little expedition through “Blow Hole”, a large cave underneath the resort. If you’re lucky, you’ll be joined by the dolphins, sea turtles, or parrot fish that frequent the reefs hereabouts.

Steps and platforms are hewn into the honeycomb cliffs, and we wondered why until we stopped at Rick’s Cafe, a famous night spot and restaurant that just happens to be next door. There, we watched the locals (and the occasional tourist) leaping into the sea from 50 foot platforms. Back at The Caves, my travel partner was daring enough to catapult himself into the 20-foot deep water from the highest platform at the resort (about 50 feet); I, being a little more cautious in nature, jumped from the 30-foot ledge. Skydiving, I can say from experience, is less punishing. But these unique cliffs and caves are only a part of what make this resort so special.

No two cabins in this intriguing resort are the same, yet all maintain a luxurious yet rustic Jamaican atmosphere.

Every piece of custom-made wood or chunky bamboo furniture is hand-painted in bold island hues. Paintings on the outside of the thatch-roofed cottages provide a clue to their names (for example, there are dolphins on the ‘Blue Dolphin’ unit and birds on ‘Bird’s Nest’).

The inspiration for this painterly approach to design becomes clear when you meet the resort owners, Betram and Greer Ann Saulter, a Rastafarian couple who both happen to be talented artists as well as successful entrepreneurs. They moved to Negril to escape the noise and bustle of city life in Kingston. When they purchased the land in 1990, it was nothing more than a couple of acres of coastal jungle choked with sea grape, almond and banana trees. The only sign of civilization visible from the property was the lighthouse perched on a cliff at the southernmost tip of the island. The region was so undeveloped that they had to home-school their children, as there were no schools (let alone and hotels or shops) in the area.

The Caves evolved out of their friendship with Island Records founder Chris Blackwell (who had a hand in launching the careers of Bob Marley, U2, The Cranberries and Steve Winwood). About the time of their meeting, Chris was opening a number of unique and funky luxury resorts under the name “Island Outpost”. [He has since sold Island Records and now focuses solely on the Island Outpost resorts.] Encouraged by Chris and resigned to the inevitability of Negril becoming a resort town, they set out to create their version of the ultimate getaway.

Betram designed the huts and the furniture while Greer Ann dreamed up the interiors. Bright colors abound and tasteful, understated luxury is evident in every detail. Stardust is the most private suite and has a mini kitchen and a balcony with fantastic ocean views. Moon Shadow has two bedrooms, ocean views, and is a great choice if you’re traveling with another couple or family. In the rooms you will find a collection of the best island music to play in the stereo. We loved the “Island Outpost” [volumes 1 through 4] CDs for their relaxed, reggae-inspired island vibes. You can pick these up at check-out for about $20 and bring home the island feeling.

The white stone walls and staircases that etch the surface of the cliffs lend themselves nicely to lounging decks where guests can tan (often topless) in semi-seclusion.

The food at The Caves is delicious island fare. From delicious plant-based fare (for those of us who are eco, ethical, or health-conscious), to fresh grilled lobster with garlic butter sauce, to perfectly seasoned and juicy jerk chicken, you won’t be disappointed. The Caves takes pride in catering to your specific needs and, in keeping with that tradition, you’re free to ask the chef to prepare virtually any meal you can think of. Breakfast starts with a course of fresh island fruits such as delicious papaya, banana (you’ve never tasted banana like this!), and pineapple. You can then order whatever suits your fancy–if you can dream it up, you got it.

One thing you absolutely must not miss is a private candle-lit dinner inside a grotto beside the “Blow Hole”. It is the ultimate fantasy dinner — I guarantee you can’t top this for sheer romance. Listen to the waves lightly lap at the rocks and admire the romance of the light of countless candles dancing on the inner walls of the cave that surrounds you, as you are served a five-course menu of your picking, by your own personal waiter. It came as no surprise to us that this is a popular spot for marriage proposals! The feeling of “just the two of us” is embodied here like nowhere else. Be sure to reserve well ahead, preferably when you book your visit.

The resort faces due West, and sunsets are breathtaking in deep shades of pink, orange and purple. At night, the cliffside steps lead to a room carved into the volcanic rock that houses a large Jacuzzi tub. Here that you can run yourself a private bubble bath and open the very large shutters to reveal the moonlit sea. After your Jacuzzi experience, you can find your way to one of the two dining and lounging areas up top and have yourself a snack, or one of the resort’s signature “Cliff Hanger” drinks. Food and drink is available at all hours of the night and desserts are always left out for those with a persistent sweet tooth.

The Caves also offers a number of spa treatments, performed in a small blue cabin overlooking the sea. Their Aveda Spa treatments range from body wraps to massages to foot reflexology. If you’re looking for more active pastimes, The Caves can arrange scuba certification ($300 US), motorcycle rentals, horseback riding, river tubing, and more. Ask for Pierre, the personable and ever-helpful manager, who made our visit all the more special by making sure that all our needs were taken care of. On our last night he even took us to a happening live music club called ‘Roots Bamboo’, where we waded in the warm water and danced on the beach to the rhythms of live reggae music.

The Caves does not accept children under 16, however, they do accept numerous celebrities (including Harrison Ford and Naomi Campbell, both loyal fans of the Island Outpost group), but expect everyone to treat them like just any other guest. Which is only fair: after all, didn’t we all come here to be treated like VIP’s?