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: Back to Montego Bay
Drive 2 hours back 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.
Day 4: Around Montego Bay
In the morning, 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.
Days 5 & 6: On to Ocho Rios
From Montego Bay, head for 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.
Day 7: East to Port Antonio
For a final look at Jamaica, 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.