Portland has one of the most picturesque country sides and boasts a stretch of seacoast extending along the northeastern tip of the island from Happy Grove to Windsor Castle. Portland is a parish of rivers and streams, sparkling water falls and secretive limestone caves. The entire coastline is dotted with caves, bays, rivers, waterfalls and verdant hills.
Port Antonio, the capital, is found on the narrow strip of land, nestled between the Blue Mountains and the generous effervescent spray from the Caribbean Sea. It has been described as one of the loveliest harbours in the world.
Rafting is one of the most popular attractions in Portland and was made a popular sport by Errol Flynn. Flynn was a Hollywood celebrity who fell in love with Port Antonio and took along his cosmopolitan crowd to taste the delights of the parish. He was intrigued by the quaint mode of transport, rafting down the Rio Grande. He and his friends are still remembered by some of the older raftsmen for their frequent jaunts down the Rio Grande.
It is said that Flynn used to sponsor rafting contests and would provide trophies and cash prizes for participating raftsmen, visitors in turn would place their bets for the winning raft.
Agriculture brought tourism to Portland and Jamaica through Lorenzo Dow Baker an American sea captain, who made Jamaica’s first shipment of bananas from Portland to the United States. Baker, an enterprising man soon realized that he could make his journey even more profitable bringing in tourists on his trips down for more bananas.
This trade led to reliable connections between Jamaica and North, Central and South America as well as Europe.