Days 1 & 2: Arrive in Jamaica and Head to Negril
Fly to Jamaica, with Montego Bay as your gateway, then transfer overland for the 2-hour drive to Negril, where you can relax, recuperate, sip a rum punch, and perhaps enjoy a reggae concert and a Jamaican buffet before turning in after an exhausting day. On Day 2, after a late breakfast and a long, leisurely morning, stake out your favorite spot along Negril's Seven Mile beach, one of the premier beaches of the Caribbean. You won't need to get up for anything, as everyone from the "banana lady" to the "ice cream man" will seek you out, but beware of marijuana (ganja) peddlers.
Day 3: Inland to Mandeville
From Negril, cut inland to Mandeville, nicknamed "English Town," lying 2,000 feet above the sea, in the highlands. Visit Marshall Pen, a 2-century-old coffee plantation home. Spend the night.
Days 4, 5, 6 & 7: Return to Montego Bay
From Mandeville, return to Montego Bay, where you can check into your hotel and then spend the afternoon on Walter Fletcher Beach, noted for tranquil waters and snorkeling. Depending on the day of the week, enjoy an Evening on the Great River or a Boonoonoonoos Beach Party.
See the historic homes at Rose Hall, former locale of the "White Witch," and visit Greenwood, former residence of the literary Barrett family. Sample jerk pork at the Pork Pit, in the center of Montego Bay. In the afternoon, take an adventurous trip at Martha Brae's Rafters Village. Enjoy an evening cruise with a Jamaican buffet and reggae music.
On Day 6, while still in Montego Bay, take the Hilton High Day Tour in the morning, then relax in the afternoon at Doctor's Cave Beach.
On Day 7, spend the morning at Cornwall Beach. After lunch, explore Jamaica Safari Village and Aquasol Theme Park.
Day 8: Runaway Bay
Plan an overnight stopover in Runaway Bay at one of that emerging resort's hotels, then spend the rest of the day at the beach or using your resort's sports facilities.
Days 9, 10 & 11: East to Ocho Rios
Continue eastward to Ocho Rios, where, after checking into your hotel, you can visit Mallards Beach, a splendid strip of white sand though often overcrowded. On Day 6, while still based in Ocho Rios, see Firefly (about a 45-minute drive east), the former home of playwright, songwriter, and actor Sir Noël Coward. On the way back, drop in at Harmony Hall, one of the former great houses of Jamaica that today sells arts and crafts, paintings, and offers good Jamaican food. Return to Ocho Rios in the afternoon for a splash in the waters of Dunn's River Falls.
On Day 11, still in Ocho Rios, explore Fern Gully, a botanical haven, in the morning, then tour Prospect Plantation after lunch. Return to Mallards Beach for the rest of the day.
Day 12: East to Port Antonio
Continue eastward to Port Antonio, former stomping grounds of actor Errol Flynn, where you can, as he did, raft on the Rio Grande. Then spend the rest of the day at San San Beach after purchasing a choice picnic by ordering peppery jerk pork or chicken at Boston Beach.
Days 13 & 14: On to Kingston
From Port Antonio, head for Kingston, capital of Jamaica, and explore the ruins of Port Royal and Spanish Town in the afternoon. Spend the night in Kingston.
Still in Kingston on Day 14, visit Devon House, the Institute of Jamaica, and the Bob Marley Museum. Call on the Frame Centre Gallery in the late afternoon. In the evening, attend a performance at one of Kingston's many theaters, such as the Ward Theatre. Overnight in Kingston and fly out the next morning.