All this and racing too? Tobago’s Angostura Sail Week

Marlon Miller explains why Angostura Sail Week in Tobago is a must on the sailing calendar. (Despite his memories, the Regatta provides some excellent ocean racing)

  • At the starting line. Photograph courtesy the Trinidad and Tobago Sailing Association/Tim Wright
  • Photograph courtesy the Trinidad and Tobago Sailing Association/Tim Wright

Captain Starboard and Commander Port may have been de-commissioned, but there is never any shortage of unique characters to liven up proceedings at the annual Angostura Tobago Sail Week.

Among those in the forefront last year were Wipers, the pencil-thin Bajan who captured both the Smooth Legs and Big Chest titles on lay day; the lady known as Fatal Attraction, who harassed a crewman on Crash Test Dummies into hiring a security detail; Stone Cold, reputedly the only sailor who could fall asleep in the middle of a race; Norman, aka Carlos, a C-Mos stalwart who simply turned his cap backwards and became the man who didn’t need any sleep, returning to his apartment at daybreak when the other participants were getting ready for the next race; and the exuberant female Brit on charter boat Mambo (Away), who took up a strategic position during the high jinks which followed the prizegiving ceremony.

They joined a long list of original personalities who have put their stamp on the “friendliest regatta in the Caribbean” over the years. Two of the best sailors around, Starboard and his sidekick Port, made their presence felt at Crown Point in the 1980s and 90s with their superhero capes and hedge-diving antics, along with Starboard’s battle cry of “faster than a rolling O, able to leap capital T in a single bound, stronger than silent E.”

But their loose ways were curtailed by marriage. Not to each other, it should be pointed out, and Port, who sailed with Ninja, is now reportedly confined to quarters, not allowed to venture outside his native Barbados for any shenanigans, on the order of Mrs Port. Starboard, a member of the Crash Test Dummies (CTD) crew, assumed his previous moniker of Fish and, with his wife and young son along last May, had to restrict himself to the odd session of break-dancing, especially the night before lay day, when hot band Joey and Friends and warm tequila got the blood boiling and the limbs gyrating.

Also getting in on the fun was English, better known as the man who built three-time racing class champion Crash Test Dummies at Soca Sailboats in Trinidad. And after watching him break-dance, most people expressed the view that it’s a good thing he has another career to fall back on. English, who prior to Crash Test Dummies was the skipper of Hooligan, had his own lament, though.

“How much longer are we going to do this? I’m 42 years old. Where are the young ones to take over from us?” he asked in between the band’s sets, his back caked with dirt and grass after another round of break-dancing.

For he had been at the forefront of the regatta’s young and reckless crowd, leading the way in nocturnal adventures, scaling the wall at the side of the Crown Point pool and plummeting into the water below, sending streams of water onto nattily dressed diners; or engaging in races on the high chairs at the hotel bar, usually ending in the pool.

Included in that bunch of rabble-rousers was Boo, a sports reporter who sailed with Legacy. Meek and mild at the best of times, Boo got led astray the only year (1993) the regatta was held on Easter weekend, and lay day was Easter Sunday. In cahoots with the unscrupulous landlubber Zando, Boo started with beers at around nine a.m. at Crown Point. They left to play golf at Mount Irvine, but at Zando’s urging decided to put the green fees to better use, buying more alcohol and other non-prescription drugs, and returned to Crown Point at dusk in time for Allan Rostant’s renowned rum shakers.

Then Boo wended his way up to the pool . . . and the rest, as they say, is history. Just as a uniformed policeman entered the Crown Point lobby, Boo decided to fulfil a long-held ambition to toss a hotel guard into the pool. But the dim-witted scribe simply returned to the lounging chair from where he had initiated the dastardly deed, and from there the policeman proceeded to haul him down to the nearby station.

In the interim, the guard, who apparently could not swim, had sunk to the bottom of the pool, from where Fish and Weasel, another Hooligan and CTD alumni, retrieved him. According to Fish, when the guard finally broke the surface, he sucked up all the available oxygen around the pool in one loud inhalation. When he caught his breath he denied he could not swim, but was merely trying to tie his shoelaces underwater.

Well, to cut a jailbird’s story short, Boo, having secured a proper lawyer when he realised that Weasel was getting him into more trouble than he was already in with his attempts to argue with the cops at the station, got bail a few hours later, after being transferred to the holding bay in Scarborough.

And a couple weeks later, having borrowed one of his father’s ties and dress shirts, appeared in court in Tobago’s capital, where everyone, including the magistrate, had a good laugh when the the charge was read out, before being ordered to pay TT$500 compensation to the guard.


Things have toned down appreciably since those wild and crazy times, so much so that last year, the crews of Ninja, Crash Test Dummies and Legacy spent most of lay day sitting on the lawn outside English’s Crown Point apartment quietly sipping the sponsor’s fine products and an occasional Bajan brew.

A member of the Saga Boy crew enquired how come they were all so quiet while the lay day activities were going on just a few hundred yards away.

“We baby-sitting!” was the reply, which was no lie as Parvo, Ninja’s main man, had his infant daughter in her pram. Just before that, another original explanation was being offered by a Bajan sailor on the telephone to his girlfriend back in Barbados  as to why he hadn’t called her since arriving in Tobago.

“They only got these ol’ rotary phones in the ‘partment and I dunno how to use ‘em!” was his excuse.

When the lounging layabouts and former delinquents eventually summoned the energy to get nearer to the official lay day activities, where extempo singers Black Sage and Big B were entertaining the crowd, they met David, a BWIA pilot who sails on Ten-shun and who conveniently booked his wife’s ticket from Trinidad for the week after the regatta. Checking the ticket the day before she thought she was due to travel, the wife discovered the “mistake” and had to enlist the help of her husband’s brother, also a pilot, to get the ticket changed and secure the jump seat on the plane as the flight was booked solid.

“If I had gotten away with it, then I would have been a hero,” joked David out of his wife’s earshot.

And he might have taken his place alongside Port, Starboard, Wipers and the other participants who have made Angostura Tobago Sail Week the place to be over the last 19 years.

They are all scheduled to be back from 12-17 May when the “friendliest regatta” celebrates its 20th anniversary.


MARLON MILLER is sports editor at the Trinidad Express. He has been covering the Angostura Tobago Sail Week since 1987, except for a few years off for bad behaviour

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