If the rough-and-tumble bustle of Kingston or the all-inclusive enclaves of Montego Bay aren’t your style, consider Port Antonio. This sleepy banana-port town in the lush northwest of the island is a side of Jamaica you may have never heard of, unless you were around in the 1940s when Port Antonio was an idyllic and popular escape for Hollywood elite like Errol Flynn who built an estate here. Port Antonio’s dense downtown area is pockmarked with dilapidated Georgian-era buildings, and just outside of town, you can see the stretch of shore that served as the set for Brooke Shields’ film The Blue Lagoon. Nature is the name of the game here, from the rolling blue surf at Boston Bay—purported to be the birthplace of jerk chicken—to the placid jungle-fringed waters of the Rio Grande, where you can hire a guide to take you on a run down the river aboard a slender, 20-foot-long bamboo raft.
Port Antonio is a 2-hour drive from Kingston's Norman Manley International Airport. You can also hop a private charter flight from the Kingston to Port Antonio.