The Hip Strip and Beyond: Discovering the True Jamaica

July 29, 2020 Updated: August 4, 2020

Once, this was Jamaica’s most storied stretch of beach. Nicknamed the “Hip Strip,” Katharine Hepburn (accompanied by playwright and director Noel Coward) once tooled along this stretch of Gloucester Avenue in Montego Bay in a Singer convertible—one that she shipped to the island herself.

John F. Kennedy and other luminaries vacationed here. The adjacent Doctor’s Cave Beach was perhaps the first on the island to attract tourists, all the way back in the 1920s.

montego bay
Montego Bay, Jamaica. (Courtesy of Jamaica Tourism Board)

And now, walking through a sultry, tropical breeze, palms audible, if not visible, shaking in the inky blackness off to my right, I see that this curving street, today renamed for local, legendary reggae and ska legend Jimmy Cliff, is rising again. The area has seen some tough times, sagging with the development of mega-sized, all-inclusive resorts aimed to keep guests within their walls, swimming and eating and drinking all in one place.

But now, anchored by a Jamaica-centric, distinctly non-all-inclusive hotel (S-Hotel), as well as Usain Bolt’s Tracks and Records (a restaurant co-founded by the fastest man on earth), as well as a statuary park dedicated to the island’s heroes and an increasing number of new clubs, the Hip Strip is back.

hip strip jamaica
The Hip Strip. (Courtesy of Jamaica Tourism Board)

Reopened in June, Jamaica became one of the first Caribbean destinations to welcome visitors again. While travelers from a small handful of states still face restrictions (proof of a negative test taken shortly before arrival is required), it’s an island big enough, and diverse enough, to encourage you to roam—and it definitely rewards those that do.

After so many months of lockdown, the joy of finding true connection, real Jamaican destinations—beyond the most popular beaches—is purer than ever. Beyond the Hip Strip, here are a few of our favorites.

The Blue Mountains

blue mountains jamaica
The Blue Mountains. (Courtesy of Jamaica Tourism Board)

Rising to more than 7,000 feet and covering the eastern end of Jamaica, these green peaks—so-named for the blue haze that often hangs around their summits—are full of surprises. Perfect for a drive, tiny two-lane roads wind along soaring ridges and down through lush valleys, with small cafes and other roadside attractions popping up, all along the way.

There’s Strawberry Hill, sitting way up, at 3,100 feet, owned by Chris Blackwell, founder of Island Records (the Gold Room here showcases his hardware, gold records awarded to everyone from U2 to Bob Marley). And Blue and John Crow Mountains National Park, a UNESCO World Heritage Site, where you can lace up your boots for a hike—some trails meander past natural springs and provide sweeping sea views, but those in for a challenge (and have up to eight hours to devote to it) can actually summit Blue Mountain, a non-technical but still-taxing climb that takes the brave (and the fit) over a 3,000-foot change in elevation.

And, of course, there’s coffee. Grown here since 1728, from just six coffee plants transplanted by the British from far-off Java, the unique ecosystem here creates some of the best beans in the world. High-altitude ridges trap the cool trade winds blowing in from the sea, settling moisture onto trees growing in the shade and rooted in dark, volcanic soil. You can tour and taste at places like Craighton Estate, an 18th-century colonial great house where you’ll sip some of their premium product while guides explain the process, then hike up, among the coffee trees, to reach a viewpoint overlooking the undulating, fertile farm.


bob marley museum
The Bob Marley Museum. (Courtesy of Jamaica Tourism Board)

Set on the southeast coast of the island and home to more than a million people, Jamaica’s capital has gotten its share of bad press over the years, but it’s still home to some of the coolest places here. Hire a qualified guide for a day tour, and hit the bustling, super-heated streets. Swing by Tuff Gong Studios, which once turned away Bob Marley, in the early days of his career. Marley was resolute in his conviction that one day he would own it, and his widow completed this wish, turning it into a global hub for reggae recording artists.

And Marley’s home in the city, where he lived from 1975 to 1981, has become a museum, and feels a bit like a reggae Graceland. A stately 19th-century residence, it still feels like a home, and tours take you past his bedroom and personal recording studio, as well as his lifetime-achievement Grammy and clothes he wore on stage. (It’s closed for the moment, but you can still stop by and spot greatness, just over the fence.)

And then, ask your guide to find a few lesser-known spots in the city. One might be Coronation Market, sometimes known as “the stomach of Jamaica,” and one of the largest markets in the Caribbean. Selling a colorful array of produce—the fruits of a fertile island—grab a few juicy items and head to a park for a picnic (Kingston has all kinds of green spaces).

Port Antonio

trident castle in jamaica
Trident Castle, Port Antonio. (Courtesy of Jamaica Tourism Board)
reach falls
Reach Falls in Port Antonio. (Courtesy of Jamaica Tourism Board)

Small, quiet, and home to eco-resorts and open-air markets, this community on the “far” side of the island—beyond the Blue Mountains, in the northeast corner—is a world away from swim-up bars and big hotels. Float on a bamboo raft down the nearby Rio Grande and get a front-row seat to life along one of the island’s longest rivers—kids swimming in its dark waters, their parents scrubbing down the laundry—before a simple lunch of shrimp and cod. Visit the Blue Lagoon or local beaches such as Boston Bay and Winnifred Beach, where you can carve out your own piece of paradise, wading into the blue waves, then recharge with jerk chicken or pork, prepared right there, near the water, at little local stands.

And take some time to wander the streets of this small town, taking in its (sometimes tumbledown) colonial architecture, browsing arts and crafts stands, and chatting with friendly people, un-jaded and happy you made the trip here.

blue lagoon
The Blue Lagoon. (Courtesy of Jamaica Tourism Board)

Castleton Botanical Garden

Even in a tropical destination, you need your moment of Zen. For that, head to one of the oldest botanical gardens in the Western Hemisphere, established back in 1862, when plants from Bath, in England, were transplanted to this fertile island. Walking these rolling, verdant 15 acres, you can almost forget about the pandemic.

Enjoy a wide variety of endemic and transplanted flora, including some 180 palms and more than 400 other plants.

Nine Mile Village

It’s not an easy road, to get there—winding through hairpin turns, you’ll roll through everyday life in Jamaica, a long way from the beach, passing through villages and farmer’s fields in Saint Ann Parish, not far from tourist hub Ocho Rios. But again, Bob Marley is the main attraction. The birthplace and childhood home of this island (and global) icon, it’s also his final resting place.

If You Go

Stay at the stylish, hyper-local S-Hotel, voted the best hotel in the Caribbean. It includes a rooftop bar and seaside pool, right on Doctor’s Cave Beach, steps from the Hip Strip. (

A number of airlines connect the United States with both Montego Bay and Kingston from New York, Miami, and other major hubs.

Plan your trip with Visit Jamaica, at

Toronto-based writer Tim Johnson is always traveling, in search of the next great story. Having visited 140 countries across all seven continents, he’s tracked lions on foot in Botswana, dug for dinosaur bones in Mongolia, and walked among a half-million penguins on South Georgia Island. He contributes to some of North America’s largest publications, including CNN Travel, Bloomberg, and The Globe and Mail.