Montego Bay & Around

  • 1 week

Montego Bay is the entry point to Jamaica for most travelers, and this one-week itinerary helps you see the most of the surrounding area while still allowing plenty of time for the beach.

Start in Montego Bay, the gateway to Jamaica for about 80% of international travelers. Hit Doctor’s Cave Beach for water sports and head downtown to Sam Sharpe Sq, taking in the historic architecture and the hustle of a real Jamaican city. Finish up with a fine meal on the Hip Strip.

Spend the next morning relaxing on Montego Bay’s beaches and maybe enjoy a cold Red Stripe and plate of jerk for lunch, but don’t linger too long. Heading east from MoBay you’ll find two great houses: the more (in)famous Rose Hall and the more authentic Greenwood Great House; we recommend the latter. Grab lunch on the north coast and relax on the beach before taking a nighttime boating expedition at Glistening Waters.

The next day give yourself a crash course in Jamaican history with a walking tour of Falmouth and its faded Georgian buildings. Finish this itinerary with a rafting trip down the Martha Brae River.

Kingston, Blue Mountains & Portland

  • 3 weeks

Take in the wild side of Jamaica with this itinerary, with the nightlife of Kingston, the rugged peaks of the Blue Mountains and the beautiful untamed greenery of Portland parish.

Touch down in Kingston for three days of sightseeing, excellent food and rip-roaring nightlife. Don’t miss the art at National Gallery and Life Yard. Take in historic Devon House, enjoying Jamaica's best patties and ice cream while you're there. Afterwards head up to Bob Marley Museum. After hours, enjoy dinner at an upscale restaurant, seguing into some of the liveliest nightlife in the Caribbean, such as the famous Dub Club. For a captivating day trip, visit Port Royal, the earthquake-shattered former haunt of pirates and privateers.

Those hills looming over the city are calling, so slip into the Blue Mountains. Enjoy the breathtaking scenery and crisp mountain air from hiking trails in Blue Mountains-John Crow National Park. The main event here is making an early-morning ascent of Blue Mountain Peak, Jamaica’s highest mountain. If you are truly adventurous, whiz down from the highlands on a bicycle tour; if such a trip seems like a bit too much, enjoy a pleasant day seeing how the Caribbean’s most prized coffee rises from bean to brewery at the one of several coffee plantations.

Descend from the Blue Mountains to Portland parish, on the prettiest stretch of the north coast. Walk the atmospheric streets of Port Antonio, taking lodging in one of the many intimate spots to the east of town or within the port’s atmospheric historic district. East of Port Antonio, you’ll find appealing communities with stellar beaches and attractive places to stay.

You can explore this terrific stretch of coast quickly or slowly, but it lends itself to some lingering. In the course of, say, five days you could go diving in the Blue Lagoon and stay at gorgeous Kanopi House, take a visit to Boston Bay, the home of jerk cooking, and stop in Manchioneal, a terrific base for visiting the sublime Reach Falls, one of the best waterfalls on the island.

The sunny south

  • 3 weeks

Take three weeks to enjoy a leisurely tour of Jamaica's south, taking in trendy Negril, laid-back Treasure Beach and the waterways of the Black River Great Morass and Alligator Hole.

Start your trip in Negril and head to the little-traveled back road that passes through the fishing village of Brighton, where you'll find deserted beaches and a slow pace of life, along with the local hot spot of Blue Hole – a perfect sinkhole for jumping into.

Linger at this quiet fishing beach for a day or three, then continue on to Black River, a sleepy port town with lovely historic buildings and vintage hotels. This is the gateway for boats into the mangrove swamps of the Black River Great Morass, a gorgeous wetlands where crocodile sightings are common. A trip up the river will take up a day of your time; afterwards visit the Ashton Great House.

In the morning head north to Middle Quarters for an unforgettable lunch of pepper shrimp at a crossroads eatery and an afternoon at the lovely YS Falls. Wet your whistle at the Appleton Rum Estate, then head south to Treasure Beach. Stay awhile in the welcoming embrace of this tight-knit community (folks seem to easily lose a month here). Be sure to take a boat trip to one of the planet’s coolest watering holes, the Pelican Bar, perched on stilts on a sandbar 1km out to sea.

From Treasure Beach, visit Lovers’ Leap for an astonishing view of the coastland. You could spend a day here walking around the sweet pastureland of Back Seaside. Continue along the coast to the fishing village of Alligator Pond. Far from packaged tourism, here you can enjoy traditional village life and unspoiled scenery at its best. You’ll also enjoy a seafood feast at a truly extraordinary beachside restaurant, Little Ochie.

If you have your own car, preferably a 4WD, and are a confident driver, head east from Alligator Pond on the ‘lonely road.’ This really is an isolated stretch of road, but you’ll find wild, empty beaches here and, after many potholes, Alligator Hole, a small preserve where manatees can be spotted.

Ocho Rios & the Central Coast

  • 1 week

One week around Ocho Rios reveals far more than just another cruise port, with stunning waterfalls and caves to explore, charming beaches and exclusive villas.

Start this trip in the tourist town of Ocho Rios. Give yourself two days to chill out around Ocho Rios, taking full advantage of the tourist menu of activities, especially the amazing Dunn’s River Falls and Irie Blue Hole.

Drive along the coast towards Oracabessa to see sights associated with James Bond author Ian Fleming, such as the lovely hotel of Goldeneye; and Galina Point for Noël Coward, whose former estate Firefly is now an excellent museum.

Turning back, head past Ocho Rios before stopping in at St Ann’s Bay to see the Columbus and Marcus Garvey monuments, then on to the Seville Great House to learn about the region's history.

Now head to Runaway Bay, where you can eat well, sleep well and base yourself for an exploration of the awesome Green Grotto Caves before continuing on to Discovery Bay and the simple charms of Puerto Seco Beach.

A taste of cockpit country

  • 1 Week

This weeklong itinerary really gets you off the beaten track, trekking deep into the hills and gorges of Cockpit Country. It’s possible to get around on this tour via route taxi, but you’ll get the most out of it by renting a 4WD.

From Montego Bay, head out to the Good Hope Estate, a beautiful great house and working plantation. Enjoy horseback riding, lunch on the terrace and tremendous views.

On narrow roads, travel to the hamlet of Windsor. Stay at the former Windsor Great House and explore Windsor Cave with the Rastafari guide or, better yet, go birding with the resident biologist and watch a vortex of bats stream out of the cave at sunset.

Get ready for some challenging but rewarding hiking. While the trails through the interior of Cockpit Country are overgrown, a half-day hike with a guide from STEA along the disused road from Kinloss to Spring Garden, along the Cockpits' east side, gives you a wonderful overview of Jamaica's wilderness.

At Rock Spring, near Spring Garden, you can explore the watery Painted Circuit Cave with a local guide before pressing on southwest to the Maroon community of Accompong, where you can meet Jamaica’s remaining Maroons.