Thanks to improved roads, it’s easier than ever to rent a car and explore beyond the island’s resort towns, from lush mountains to hidden coffee plantations — just follow this itinerary.
Strawberry Hill hotel, Jamaica
Credit: Melanie Lieberman

Jamaica may be best known for its beachy resort towns and all-inclusive resorts, but it's easier than ever to explore the eastern half of the island. Rent a rugged 4x4 in Kingston and head straight to the island's lush Blue Mountains, home to stunning coffee plantations, ultra-luxe resorts, and quiet slivers of pristine beach.

Day 1

It’s only an hour’s drive from Kingston to Strawberry Hill, music-industry icon Chris Blackwell’s mountaintop retreat, but you’ll gain 3,100 feet in elevation while navigating a series of hairpin turns. Check in to a villa with commanding views, then take a dip in the hotel’s infinity pool.

Day 2

Strawberry Hill is within walking (or hiking) distance to some of the region’s best coffee plantations. Set out on an easy three-hour guided hike to Clifton Mount — the oldest functioning coffee estate in the country — on the eastern edge of Catherine’s Peak. On your return, grab dinner at EITS Café, which serves European-influenced Jamaican dishes.

Day 3

After breakfast, begin the three-hour drive through Blue and John Crow Mountains National Park to Port Antonio. At the Trident Hotel, you can splurge on a helicopter flight and customized tour of the Wallenford Coffee plantation, which includes a hike deep into the valley and the chance to harvest coffee berries. Then retire to one of the hotel’s 13 ocean-​front villas, which have private terraces and soaking tubs.

Blue Mountains, Jamaica
Credit: Melanie Lieberman

Day 4

Take a scenic drive back to Kingston along Jamaica’s eastern coast, stopping for jerk chicken at the food stalls along Boston Bay Beach. Spend the night at Kingston’s modern Spanish Court Hotel, which features furniture and photographs by local designers and artists.

Day 5

Sample some of the best patties on the island at the nearby Devon House, before heading to YS Falls — an upscale swimming complex with three pools and a seven-tiered waterfall that spills out of the adjacent jungle. In the evening, pull over in Treasure Beach, an hour away, and book a colorful cottage at Jakes Hotel, which perfectly captures the laid-back, hippieish vibe of the area.