Of all the islands in the Caribbean, the one with the most character has got to be Jamaica, located just south of Cuba in the Greater Antilles. Here, amidst the wafting scents of rasta life and relaxed rhythms of reggae, the pace is decidedly slow—even by island standards.
But up on Jamaica’s north shore, there’s plenty of action to be found for visiting golfers, beginning with the island’s crown jewel: The Tryall Club. The course at this 2,200-acre plantation hosted the Johnnie Walker World Championship from 1991-95. Its front nine hugs the sea, while the back whisks you up on a hillside, where the challenges multiply and views astound. Accommodations at Tryall come in the form of luxurious villas (with room for lots of friends), making you feel like a bona fide plantation owner, while dining in the resort’s Great House is a longstanding island tradition.
Just east of Montego Bay is Half Moon, a classic 1950s-era resort that has welcomed royalty of every stripe, from Queen Elizabeth II to the Kennedys to stars of stage and screen. The Robert Trent Jones golf course is quite possibly the island’s toughest, in large part due to its phalanxes of palm trees.
Up the road a few miles, near the terrific Rose Hall resort, two more courses vie for island honors. The dramatic White Witch and Cinnamon Hill courses there are wonderfully hilly, challenging, and fun. And don’t miss the chance to visit Scotchie’s while you’re in the area: It’s the epitome of the Caribbean roadside beach bar.