Jamaica’s second largest city lies on the island’s northwest shore, wrapped around a bay that has sheltered Spanish galleons and English pirate ships, royal yachts, and cruise ships. “Mo Bay” became a playground of the rich and famous in the 1950s.
Nowadays, Montego Bay's allure is manifold: golf courses, outdoor sports, and alfresco party spots. The “Hip Strip” on the bay’s eastern edge is renowned for its rowdy dance clubs. In the lush mountains behind Montego Bay is wild Cockpit Country, a corner of the Caribbean that’s little changed since the pirate days.
Breakfast: Pelican Grill – Most of Montego Bay's best restaurants don’t open till lunchtime, but the Pelican gets a 7 am start with breakfast that attracts a steady stream of locals and visitors who’ve been out partying all night. The menu is a mix of American dishes, like bacon and eggs and omelets, and Jamaican fare, like saltfish and ackee, boiled plantain, and fried dumplings.
Lunch: Seagrape Terrace – Ask for a table beneath the almond trees and soak in the view before diving into dishes like the spiny lobster and smoked marlin platter or the grilled catch of the day. And leave room for dessert — especially the Blue Mountain coffee trio of cheesecake, mousse, and ice cream.
Dinner: Seahorse Grill – A favorite of Jamaicans, the yacht club’s popular alfresco restaurant’s menu mixes international and Jamaican favorites, with an emphasis on fresh seafood like whole red snapper, curried conch, and smoked marlin. For dessert, dig into a slice of sweet potato coconut pecan pie, served hot and topped with rum raisin ice cream. Even if you aren’t in port late enough for dinner, go for rum-laced cocktails on the edge of the dock.
Drinks: Pier 1 – This energetic waterfront bar is known for live music (reggae, dance hall, ska), great people watching, and a center-of-the-universe vibe that attracts hundreds of visitors and locals each night. If the Pier 1 scene is too rowdy for your taste, try the mellow Blue Beat jazz lounge on Gloucester Avenue.
Tip: The island’s venerable Appleton distillery, founded in 1749, makes what many connoisseurs consider one of the world’s top rums: Appleton Estate 21 Year Old. Its smoky flavor is complemented by hints of vanilla, cocoa, orange, and almond. Don’t dare order it in a punch: It has been aged for two decades in oak barrels and should be sipped like scotch.
For Everyone: Rose Hall Great House – Rose Hall is the most celebrated of the great plantation houses scattered across Jamaica. Erected in 1770 as the centerpiece of a sprawling sugar estate, the house eventually passed into the hands of Annie Palmer, the notorious “White Witch of Rose Hall.” During her tenure as the plantation master, Annie supposedly killed several of her husbands and slave lovers, and was eventually murdered herself. Locals say her ghost and those of her victims still haunt the massive Georgian mansion, which you can tour.
For Couples: YS Falls – Located about an hour drive south of Montego Bay, these seven cascades tumble into jade-colored pools in a jungle-shrouded gorge. The lower pools are less crowded and more secluded, private enough to snatch a kiss or two. Swing on the Tarzan rope, tube down the river, or explore the forest canopy on the zip line that dangles above the falls. Think of this as Dunn’s River, without the crowds.
For Families: Falmouth – Rent a car or take a taxi to Falmouth, located 18 miles east on the new coast road. Tour the historic downtown area on the Falmouth Trolley and soak up the ambience of a seaport that, 200 years ago, was one of the most important in the Caribbean. Learn about island wildlife — and get up close to crocodiles and boa constrictors — at the Jamaica Swamp Safari Village. Or pop into Greenwood Great House, the plantation once owned by the family of English bard Elizabeth Barrett Browning.
For the Adventurous: Cockpit Country – Southeast of Montego Bay is the island’s largest remaining wilderness area, a rain forest dubbed Cockpit Country. Runaway slaves evaded their British colonial masters by hiding in the region. Nowadays, the area is rife for jungle hikes, underground caving, bird watching, and float trips down pristine streams; Cockpit Country Adventure Tours offers many options with knowledgeable local guides.
The Spanish landed the first horses in Jamaica in the 1500s and since then, the island has developed a rich heritage for equestrian sport. Half Moon Equestrian Centre organizes trail rides along the beach and into the surf, as well as lessons and pony rides.