Today it's still popular with the stars, counting Beyonce, Scarlett Johansson and Tom Cruise among its fans
There is even a harbour, Errol Flynn Marina, named after the Hollywood actor who owned an island off the coast
That Hollywood rabble-rouser Errol Flynn went out on a limb about Port Antonio.
'It's more beautiful than any woman I have seen,' he said. The charmer. Mind you, Flynn was something of a connoisseur.
Married three times, when he died aged 50 in 1959 he was living with the teenage actress Beverly Aadland.
Dreamy: It is clear to see why the stars flock to Port Antonio. Pictured is a classic island beach with golden sands and vibrant vegetation
Dreamy: It is clear to see why the stars flock to Port Antonio. Pictured is a classic island beach with golden sands and vibrant vegetation
Flynn, who owned a small island off the coast of Jamaica, loved to sail, so it's fitting that the harbour is now called the Errol Flynn Marina.
Fitting, too, that Port Antonio and the unspoilt stretch of coast to the east is beginning to echo its Sixties and Seventies heydays when Richard Burton, Liz Taylor and the Aga Khan had the carefree time of their lives.
'Raw Jamaica' is how the petrol pump attendant puts it. Which means easy-going, uncrowded, friendly.
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Crucially, the Portland parish — as it's known — is the home of jerk chicken. Nowhere takes it more seriously, nowhere does it better.
Another thing: there's more rain here than anywhere else in Jamaica, so it's greener, lusher. It's old school, but with a modern vibe.
Which is a goodish way to describe Trident, a sleek hotel a mile outside town that has been brought back to life by the Geejam group, with a sister hotel about ten minutes away high up on a hill, complete with its own recording studio.
Star appeal: High profile names such as Beyonce (pictured), Scarlett Johansson and Tom Cruise have all visited the Portland area
Star appeal: High profile names such as Beyonce, Scarlett Johansson (pictured) and Tom Cruise have all visited the Portland area
Star appeal: High profile names such as Beyonce, Scarlett Johansson and Tom Cruise (pictured) have all visited the Portland area
Star appeal: High profile names such as Beyonce, Scarlett Johansson and Tom Cruise are all fans of the spellbinding island
Gorgeous: Port Antonio and the unspoilt stretch of coast to the east is beginning to echo its Sixties and Seventies heydays when Richard Burton, Liz Taylor and the Aga Khan had the carefree time of their lives
Gorgeous: Port Antonio and the unspoilt stretch of coast to the east is beginning to echo its Sixties and Seventies heydays when Richard Burton, Liz Taylor and the Aga Khan had the carefree time of their lives
Beyonce, Scarlett Johansson and Tom Cruise have all checked in here.
There are only 13 villas at Trident and they are all huge, with plunge pools that double as spa-baths and patios that face the rumbustious Caribbean Sea.
It's so rumbustious and rocky here that you can't swim from the villas, but if you wander down a path and through an arch you arrive at the hotel's private beach, a charming inlet where the waves give way to calm, clear waters.
'Is there anything else we can get you?' asks a member of staff as he points out the Bose music system and the outdoor bath tub.
'Well, I would love to get a CD of Harry Belafonte's Day O — the banana song,' I tell him, sheepishly.
'See what I can do,' he says Belafonte recorded the calypso tune in 1956 and Port Antonio was its inspiration, as in 'Stack banana 'til the mornin' come, Daylight come and me wan' go home'.
On Friday nights, most guests at Trident are taken up to Geejam where the Jolly Boys perform live. This troupe has been together nearly 60 years and specialises in mento music — reggae covers of well-known hits.
In his name: Errol Flynn, who owned a small island off the coast of Jamaica, loved to sail, so it's fitting that the harbour is now called the Errol Flynn Marina
Jon Baker, the British music supremo who owns Geejam and manages Trident, revived their careers a few years ago. Yes, the lead singer's voice is not what it once was but, then, nor is Bob Dylan's and some of us still pay good money to hear him.
On Saturday night, the action is back at Trident at Mike's Supper Club, where an eight-piece jazz band, complete with a red 1917 Steinway, performs with aplomb, while you plough through the Japanese-Jamaican fusion menu.
A crazy combo, for sure — but Jamaica is good at crazy.
You can also hire an old banger to explore the coast.
On Saturdays and Sundays, Boston Bay becomes jerk chicken central, with Mickey's assuming the role of market leader. Music blares, artisans sell their wares, smoke (both legal and illegal) rises into the air.
Film set: Nearby is Blue Lagoon (pictured), forever associated with the film of the same name, starring Brooke Shields as a 14-year old nymphet — although some people insist the movie was shot in Mexico
Go with it all, then head down to the beach and you'll soon be agreeing with Christopher Columbus who in 1494 described Jamaica as: 'The fairest isle mine eyes ever beheld ... '
Our favourite beach is Winnifred, which, confusingly, is in Fairy Hill. There are no signs and it's a bumpy track down to it. Not so long ago, the government wanted to sell it to a developer, but the locals fought hard and it ended up before a judge, who ruled in favour of keeping it public.
Nearby is Blue Lagoon, forever associated with the film of the same name, starring Brooke Shields as a 14-year old nymphet — although some people insist the movie was shot in Mexico. No matter, it's a special spot and you'll be tempted to go on a bamboo raft tour.
Frenchman's Cove is another star, but you have to time it right. Such is its allure (a curve of sand, tropical trees and shrubs bowing their heads to the ocean, a fresh-water river winding its way back to a beautifully kept garden) that busloads of day-trippers come here for lunch.
So arrive early or late in the day. Many people think this is the world's most beautiful beach.
On our second evening at Trident, there's a knock on the door. A member of staff is holding what looks like a blank CD. In fact, he has downloaded the Belafonte song on to a CD and apologises that he could not give it to us sooner.
'That's why I love the Caribbean,' says my wife, as I put the disc in my laptop and crank up the volume. We belt out the chorus. I'm badly out of tune but, hey, I feel like one of the Jolly Boys.mailonline
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