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The Spanish christened the bay ‘Puerto Anton’ in the 16th century, but made no serious effort to settle. In 1723 the British laid out a rudimentary town on the peninsula and named it Titchfield; a fort was added in 1729. But rampant fevers in the swampy coastlands and constant raids by marauding Maroons deterred all but a few settlers.

Following peace with the Maroons in 1739, Titchfield expanded. Many settlers grew sustenance crops, including bananas. Enter the Yankee skipper Captain Lorenzo Dow Baker (1840–1908), a fruit-shipping magnate, who arrived here in 1871 and established the banana trade that created a boomtown overnight. Baker and his Boston Fruit Company went on to own 40 banana plantations from Port Antonio to Buff Bay, making Port Antonio the ‘banana capital of the world.’ Port Antonio grew so wealthy that, it is said, planters would light their cigars with US$5 bills.

In the 1890s Baker began shipping tourists from the cold US northeast in his empty banana boats. Although Portland’s banana bonanza was doomed in the 1930s by the onset of Panama disease, the arrival of movie star Errol Flynn and, later, numerous bluebloods and Hollywood stars, gave new cachet to Port Antonio as a tourist resort.

In the 1960s a second brief heyday occurred when a luxurious resort went up ­overlooking Frenchman’s Cove. This was followed by Prince Alfonso de Hohenlohe’s equally exclusive Marbella Club at Dragon Bay. The regal resorts attracted the jet set crowd, and the coves east of town were colonized by the very rich, setting a trend that still continues.

Today, as in the past, all of the bananas exported from Jamaica depart from Port Antonio’s dock. The loading of the fruit is now mechanized, so you will no longer see the tallyman tallying bananas or stevedores ‘working all night on a drink of rum.’