One of the peculiar developments of late-20th-century society is the proliferation of the all-inclusive vacation resort. You might call it the “McDonaldization” of luxury travel: Wherever you go, you rest assured that there’s a meticulously maintained hotel and resort facility with predictable meals, predictable leisure activities, and predictable crowds. The architecture of these places can best be described as “Disneyland meets Venetian palazzo.” And in these pastel-colored villas, rotund guests rip through the buffets … morning, noon, and night. Predictability is king. On the island of Jamaica, these prepackaged places have cute names that often conjure up images of casual footwear.

Of course, the best way to experience Jamaica isn’t by hiding out in any of these cookie-cutter hotels. Take to the road instead.

In Jamaica, you’ll find few stoplights and no expressways. Along its winding, rural roads, you’ll face rugged mountain vistas, breathtaking stretches of coastline, and an endless variety of resorts. Variety is the spice of life, especially when it comes to experiencing the gem of the Caribbean.

Those who follow Motoring+ know that it helps to be freshly trained to drive on the left side of the road in any part of the former British Empire, and Jamaica is no exception. It also helps to remember that a frenzied driver from New York City has to slow down on this island and yield to an array of farm animals, which tend to utilize the roads better than the automobiles do.

It’s best to start your trek just outside Montego Bay, at the charming Half Moon Club. On the walls of the clubhouse lobby are photos of the Main Line Philadelphia crowd that wintered there mid-century, alongside visitors such as Princess Anne and first lady Jacqueline Kennedy. It’s situated on 400 acres with some of the best golf on Jamaica.

Although black tie is no longer required at Half Moon after 6 p.m., it wouldn’t exactly be out of place, either. The resort is a spot for celebrities and financiers to see each other and be seen, all while having the time of their lives.

Driving west along Jamaica’s northern coastline brings you to Ocho Rios, home to the Jamaica Inn. This is where Prime Minister Churchill often came to sit on the beach with his oil paints, a proper reward, we think, for saving civilization from the Nazis. It’s a fun historical fact that reflects well the groove at the Jamaica Inn even today.

The villas, including the one cherished by the Churchills, are relaxed and comfortable. And the inn’s new spa facilities are more of the same: An outdoor terrace overlooking the sea is where you can receive a four-handed massage, the pièce de résistance of the spa world.

After that, you’ll be more than limber to make the next leg of the drive, backtracking west to Montego Bay and then to Jamaica’s southern coast.

There you’ll find Round Hill, where movers and shakers such as Ralph Lauren go to escape the pressures of the business world. (The son of the Blackstone Group chairman, Stephen Schwarzman, got married there last month.)

Round Hill oozes preppy, Eastern Establishment style: Mr. Lauren himself decorated some of the clubhouse lounges. Each of the lavish hillside bungalows has its own pool, a delightful extravagance for society doyennes who sometimes prefer not to mingle with the other members at the beach.

Leaving Round Hill and heading to Jake’s on Treasure Beach is sort of like ditching a chauffeur-driven Rolls for a fun-filled jaunt with friends in a VW bus. That is to say, it’s often more relaxing to go bohemian. Sleep under the stars on the rooftop of a beachside hut and enjoy the food. Treasure Beach is in the Jamaican parish of St. Elizabeth, the island’s so-called breadbasket.

No Jamaican drive would be complete without visiting the west coast town of Negril. The Caves is a boutique resort (there are just 10 villas) owned by Chris Blackwell, the impresario who brought the sounds of Bob Marley and his reggae music to the rest of the world.

The Caves is extraordinary. The entire resort sits on enormous limestone cliffs overlooking the Caribbean. This means that you can get up from your breakfast table, walk five steps, and then take a 30-foot plunge into the sea. In fact, we’ve seen it done.

Respect, man. It’s what you learn to dole out in Jamaica, and if you do so along your drive, this island and its people will reciprocate. There’s even a good chance they’ll have a car waiting at the airport for you when you return.