a close up of a flower garden in front of a house with White Witch of Rose Hall in the background

The fourth largest island in the Caribbean, Jamaica has long beckoned those in search of sun and sublime beaches with its laid-back attitude. But what the island has really mastered is offering travelers the opportunity to be as relaxed or adventurous as they like. Follow our lead for a week-long itinerary around the island that will have you sampling exotic fruits, dipping into a bioluminescent lagoon and eating flopping-fresh seafood with your toes in the sand. Perhaps more than any other Caribbean destination, Jamaica is full of surprises. 

a large waterfall over some water

The freshwater falls descend some 600 feet in swiftly moving cascades and pools until flowing directly out into the ocean, offering the best of both worlds for a refreshing dip. For another option for spending a great day on the water, book a sailing excursion on the 40-foot Jeanneau sailing yacht, Lark. You can opt for half or full-day sailing trips that depart from the marina in Montego Bay and stop for snorkeling at Fish Pond Reef and lunch onboard. 


To really get away from the tourist masses, plan to spend some time on the pretty curve of land in Jamaica’s remote northeast corner, where steep mountains plunge to the sea in Port Antonio in the parish of Portland. The agriculture-rich area is Jamaica’s breadbasket, and banana trees, orchids and palm trees bloom everywhere. You can go on a rafting trip on bamboo rafts along the stunning Rio Grande River, then follow it up with a delicious crayfish feast at Soldier Camp, a hard-to-find restaurant that’s worth the effort for the authentic dishes served up. For a dream beach, plan to while away some hours at Frenchman’s Cove, where a spring-fed river flows into the sapphire sea, or join the surf crowd at Boston Beach, just a bit farther east.

Continuing along the coastal road from there, you’ll soon come to Boston Bay, Jamaica’s most famous spot for sampling the island’s famed jerk meats. It can be a bit overwhelming as vendors shout out their offers to newly arrived tourists, jockeying for business, but whoever you end up sitting down with you won’t go wrong with an order of spicy jerked chicken or ribs and a cold Red Stripe to wash it all down. Finish a perfect Port Antonio day with live mento music (made-in-Jamaican music that pre-dates reggae) performed by native sons, the Jolly Boys. The band puts on a rousing performance every Friday night at Bushbar, a sweet little alfresco spot high in the hills.