Port Antonio did not develop until Portland was established as a parish in 1723. Originally called Titchfield, the town was concentrated on the peninsular hill dividing the twin harbors that still retains the town’s original name. Port Antonio, like much of the eastern side of the island, was not developed in the early colonial period thanks to the rough terrain not suitable for sugar, the principal cash crop during the slavery period. To further dissuade European settlers, the Maroons had their eastern stronghold inland from Port Antonio in the Rio Grande Valley.
Port Antonio was completely transformed, starting in 1876, by the banana trade, which turned the hills into lucrative plantations in a way sugar never could; the area grew further in recognition when the empty banana steamers returned with New Englanders who’d heard about paradise in Portland, Jamaica. Steamer captains George Busch and later Lorenzo Dow Baker basically invented the lucrative banana trade by encouraging local farmers to plant the "green gold" as they fed an exploding, almost accidental demand in the northeastern United States. Jamaica dominated world banana production until 1929, when Honduras took over as top producer after blight destroyed Jamaica’s crop. But this was not before Baker was able to invent a new trade in tourism, building the Titchfield Hotel, one of the most extravagant hotels in the Caribbean, which enticed the world’s early steam-set to discover Port Antonio. Tourism dropped off during the Great Depression, but the area experienced a brief resurgence in the 1950s and 1960s when it became a chic destination for Hollywood stars, with the likes of Errol Flynn and Ian Fleming making it their preferred stomping ground. Some of the world’s wealthiest people visited and bought property in the area. Since then Portland has been somewhat overshadowed in promotional efforts by tourism developments in Ocho Rios, Montego Bay, and Negril.