Jack no doubt was dismayed that his marauding career was at an end. But, if you’ve got to live in captivity, you can do a lot worse than Negril. For years, this sleepy town languished at the western end of Jamaica. But after the government built a road in 1959, tourists began to trickle in. That trickle turned to a flood in the ‘70s as young Americans and Europeans arrived to tune out and turn on. The counterculture ambiance merely enhanced Negril’s reputation as Jamaica’s lush, laid-back and, at times, licentious center for do-as-you-please vacations.

If you’re looking for fun in the sun, you’ll find it in Negril. The first thing you’ll want to do--indeed, you’ll feel compelled--is to hit the beach. The bow-shaped town hugs Seven Mile Beach, the longest continuous stretch of powdery shore in Jamaica--and one of the Caribbean’s most magnificent. As you stroll along the butterscotch sand, you’ll encounter locals taking a dip, lovers embracing under swaying palms, families enjoying picnics, children splashing in the shallow foam, and, in a few spots, sun worshippers performing their devotions au naturel. Tug off your trunks and join them. Or continue down the shore, past grotto-lined cliffs, until you reach Negril Lighthouse, erected in 1895 at the south end of the beach.

It’s a wheezing hike up the lighthouse’s staircase, but if you stick it out you’ll be rewarded with panoramic views of the bay and the sparkling Caribbean Sea, which seems to stretch to infinity. Beneath those calm, clear ribbons of emerald, teal and turquoise are treasures even more remarkable. Negril is ringed by magnificent coral reefs that nourish and protect a variety of marine creatures: squirrel-fish hiding in crevices overhung with red rope sponge; yellowtail snappers and parrotfish nibbling at the seaweed.

On the northwest coast, Montego Bay is Jamaica's 2nd-largest city and its capital of tourism.

By day, tourists from cruise ships scour crafts markets and duty-free boutiques. By night, they groove to the rhythms that shake the foundations of clubs along the ocean-front Gloucester Avenue. The heart of the Jamaican Riviera, Montego Bay is a paradise of palm-covered hills edging toward sun-warmed beaches and turquoise sea. But there's more to Montego Bay than tourist attractions. This is a city rich in history and tradition. Close your eyes and imagine what life was like when plantations reigned supreme.

Montego Bay's elegant Great Houses were built centuries ago by English planters, whose farms supplied Europe with sugar, rum and bananas. Rose Hall, the most famous of the city's manor homes, attracts visitors from around the world. And Greenwood House, built by a cousin of poet Elizabeth Barrett Browning, features an extensive collection of rare musical instruments. But don't get the idea that Montego Bay is a stuffy museum. Aristocrats built their homes here because of its sublime climate. Even Columbus was impressed by Montego Bay, christening it El Golfo de Buen Tiempo, the Gulf of Good Weather. Less-romantic Spanish adventurers renamed the place Bahia de Manteco (Lard Bay). But Jamaicans today know this bustling, beautiful slice of heaven by one name only: Mobay.

Just off the coast from Sangster International Airport are 10 square miles of spectacular coral reefs, teeming with marine life.At the turn of the 20th century, weary travelers flocked here to take the cure at Doctor's Cave Beach. The waters may not be as restorative as an English doctor of the time declared. But the beach is, nonetheless, one of the Caribbean's most beautiful, with wide patches of sand peppered with sea grapes and almond trees.

Anglers come here from around the world to haul in blue marlin. And boat lovers love Montego Bay as well. The Montego Bay Yacht Club, in fact, hosts the biannual Pineapple Cup race. On land, there's much to do as well. Golf is superb in Montego Bay, which boasts four 18-hole championship courses, including world-renowned Tryall. Good Hope Plantation offers miles of winding trails for horseback riding. And Montego Bay was made for shoppers. At the Harbour Street Crafts market, vendors tempt tourists with straw bags, batik wrap-arounds and wood carvings. Duty-free shops offer everything from perfume, cigars and liquor to china, crystal and Scottish cashmere. And the "Hip Strip" of Gloucester Avenue pulses with restaurants, art galleries and stores. Nights in Montego Bay are as varied as the city itself. You'll find everything from elegant restaurants to intimate seaside cafes and stands selling spicy local favorites. And on the music scene, reggae reigns in Montego Bay, home of the annual Reggae Sumfest in August.

"Kingston is the largest English-speaking city south of Miami, rich with historic and cultural attractions, world-class shopping, gourmet restaurants and sizzling night spots."

The city’s rich colonial heritage is hallmarked as well at Kingston Parish Church, where tombstones date to 1699. And at the crowded square known as the Parade, you can almost envision the British soldiers who once drilled here. In nearby Port Royal, relics at the Museum of Historical Archaeology remind you of the swaggering pirates who roamed the western Caribbean in the 17th century. With permission, divers can explore sunken pirate treasures at the end of the Palisadoes Peninsula that hugs Kingston Harbor.

And at Spanish Town, a short drive from Kingston, visitors can learn what island life was like in 1523, when conquistadors built the Cathedral Church of St. James, the cornerstone of their colonial capital. Kingston’s natural attractions are as breathtaking as its historic venues. Hiking is sublime in the towering Blue Mountains, where you can tour plantations that produce coffee prized the world over. Or you can stroll through the 200-acre Hope Gardens near the University of West Indies campus. Dating from 1881, the park features an orchid house and small amusement park for children. Year-round balmy weather brings golfers to Caymanas and Constant Spring courses. Visitors as well can take in a polo match at Caymanas Park, or savor the sport of kings as thoroughbreds round the bend at Caymanas Race Track.

Just as many treasures await off shore. In the beautiful Caribbean surrounding Kingston are canyons and crevices full of shimmering fish, as well as star, rose and giant pillar corals. If culture is your cup of tea, catch a show at the Little Theatre, thrill to the music of the Philharmonic Symphony, enjoy a performance by the National Dance Theatre Company or peruse the National Gallery’s impressive collection of Jamaican art. Shoppers can take home artful wood carvings and other crafts, as well as a full line of duty-free goods. And you’ll love Kingston’s many restaurants, which serve up local and international specialties with Jamaican flair. After dinner, dance a starry night away at Asylum or another of the clubs and discos that line Knutsford Boulevard.

It is the heart of Jamaica, this thriving capital city on the island’s south coast. Home to 850,000, Kingston is the largest English-speaking city south of Miami, rich with historic and cultural attractions, world-class shopping, gourmet restaurants and sizzling night spots. But there comparisons end, for Kingston is like no other city. Listen. On any corner you can hear those lilting, infectious rhythms that make you want to get up and dance. If Kingston is Jamaica’s heart, reggae is the blood that keeps it pumping, and it was in Kingston’s back streets that the music was born.

Smell. From family-owned restaurants waft the aromas of I-tal, the vegetarian cuisine of the Rastafarians, whose complex, cherished devotions took root here before radiating throughout the world. Look. The majestic Blue Mountains soar more than 7,000 feet and the Caribbean Sea shimmers like a net full of jewels.

Overlooking the world’s seventh-largest harbor, Kingston is the center of Jamaica’s government and commerce, a beguiling city whose cosmopolitan ambiance contrasts with the laid-back atmosphere that pervades the rest of the island. Kingston once was the administrative hub of Britain’s Caribbean colonies. Step back to those days when you visit Devon House. A portico rimmed by stately columns welcomes visitors to this sprawling mansion, one of the finest surviving examples of Georgian architecture. Inside, sparkling chandeliers and ornate rosettes on ceilings bespeak the elegance of a bygone era.