I step out of the air-conditioned chill of Norman Manley International Airport and into the muggy Jamaica night air, happy for a short reprieve from wintry New York. My driver watches with amusement as I head for the car door. “Will you be driving?” he asks. It dawns on me that I approached his vehicle Yankee style, on the right. We laughed; I went left and settled in for the winding ride across the peninsula highway leading to Kingston. 

In the past, I’ve enjoyed the laid back vibe of Ocho Rios, Montego Bay and Negril. This time, I headed southeast for the capital’s celebrated City Run, and looked forward to experiencing Jamaica’s citified side. 

Day one was filled with sightseeing, a beach romp, and partying with good eating in between. First stop: Spanish Town. As its name suggests, Spanish Town—13 miles west of Kingston in St. Catherine Parish—was settled by the Spanish in 1534, and was the island’s capital through British rule until 1872. We eventually arrived at Emancipation Square, the former governmental hub and home to the most expansive assortment of Georgian style architecture in the Caribbean.

Emancipation Square is also where Queen Victoria’s royal decree freeing the island’s slaves was read in 1838. To envision colonial Jamaica, we toured the People’s Museum of Craft and Technology, housed in former stables near by. Our engaging guide led us through various collections of artifacts—cooking utensils, ceramics, basketry, building materials, even games and toys—as well as oldfangled machinery for processing the sugar and coffee that made Jamaica prosperous.

Next was Fort Clarence Beach Park, a popular destination among locals. Families, couples and groups of teens picnicked under knotty trees, frolicking intermittently in the vigorous waves. We hit the beach’s food shack for our pick of freshly caught fish for steaming or frying.

During the wait, we refreshed ourselves with bottled cranberry water, then elevated to homeland favorites like Red Stripe beer and Appleton rum. As a Marylander, I appreciate good seafood and my beachside meal (parrotfish deep-fried to golden brown perfection, with bammy and festival) did not disappoint.

Later, in a nod to the upcoming 5K Kingston City Run, we dined at Tracks & Records sports bar, owned by Jamaica’s patron saint of sprinting, Usain Bolt. It’s a lively, sprawling, state-of-the-art venue that reflects the Olympian’s love of sports, music and fine food. Vinyl albums adorn walls, and dozens of flatscreen TVs air sports from around the world. R&B, reggae and soca blare, in the tradition of Jamaica’s booming sound systems.

The menu consists of traditional cuisine like jerk pork, stew beef, peppered with fusion dishes like jerk chicken quesadilla, callaloo-topped flatbread pizza spiked with Scotch bonnet oil, and ital penne with pumpkin, plantain and cho-cho in coconut cream sauce. Superb cocktails were served from an expansive bar with Guinness available on tap. 

We capped off the evening at a massive outdoor party that kicked-off the island’s bacchanal season at Kingston’s National Stadium. Soca ruled the night as three different DJs alternately stormed the stage, hyping the crowd of mostly young revelers who’d jump up and wind until the wee hours.

Every day, I awoke to stunning views of the majestic Blue Mountains. One day I journeyed up a steep road with nail-biting bends and twists to experience them. High up on a plateau, our group met Susan de Campos Palermo, who led us to her off-road bed-and-breakfast RafJam, nestled amidst lush foliage, two tranquil streams and a waterfall. There you could hike, bird watch and camp out, or opt for relaxing pursuits like outdoor yoga or a massage.

Later, we were treated to scrumptious lunch and breathtaking vistas from the veranda at Strawberry Hill, one of three resorts owned by Island Records founder Chris Blackwell. With its posh Caribbean-style cottages and exquisitely landscaped gardens, Strawberry Hill is a magnet for the celebrity set: Grace Jones, U2, the Rolling Stones and Naomi Campbell have all been guests. But locals also visit to enjoy fine nouvelle Jamaican cuisine and the awesome view.

Caribbean folk have a knack for celebrating their events, and the carb-up party held the night before the Kingston City Run was no exception. Some of the islands’ top chefs and culinary artisans gathered in the garden of the popular Pegasus Jamaica hotel and prepared tasty pasta dishes for race participants or anyone else who cared to try.

Early race day morning, you could feel the excitement in the air, as crowds of people outfitted in their finest running gear headed to the 5K starting point in Kingston’s business district. Seasoned runners, weekend warriors and plenty of spirited strollers started with gusto at the crack of the gun for a race that lasted a little over an hour (depending on your pace).

The course took us through historic landmarks like Devon House and the Kings House grounds, past beautiful old homes, exclusive gated communities, and sleek apartments with volunteers at points along the way cheering and distributing water. Near the finish line, participants gathered at Emancipation Park for music and refreshments, as exuberant winners took the stage for prizes and pictures. Race proceeds benefit charities helping the island’s homeless.

Before leaving, I made a pilgrimage to the Bob Marley Museum housed in the legend’s former home. Just entering the vibrant yard with its brightly colored flora, eye-catching murals and nonstop Wailers music put me in an irie mood.

Inside, an impressive array of gold and platinum records and various awards line the walls. One room is cleverly wallpapered with news clippings from his final tour. Just as interesting are the modest possessions on display: a favorite denim shirt; his juice blender; and a star-shaped guitar on his bed. The tour ended with a short film of the man himself sharing his wisdom and philosophy. I left Kingston feeling mighty all right.

—Julia Chance