Before this year’s Carriacou Regatta, all the talk was about Windward Pride. She didn’t fail to deliver.

Last minute preparation aboard Windward Pride
By S. Brian Samuel
The 2023 Carriacou Regatta was preceded by a higher-than-normal level of hype and braggadocio among captains and owners, and I’m pleased to report that the racing fully lived up to all expectations — and then some!
One month earlier, the boatbuilding village of Windward in Carriacou saw a rare and special event: the launching of a new wooden sloop, purpose-built for racing. Well, not new, but certainly very much improved. American Eagle was a racing sloop owned by Winsley McLaren and raced for several years, without ever achieving its potential. After failing to complete a single regatta in ten years, American Eagle was laid up on the hard in Windward, heading to a slow death at the hands of the weather. Fortunately, in January 2023, Eagle was bought by three young Carriacouans (aka Kayaks): Floyd Davidson, Richard McQuilkin and Hubert McLawrence, thereby rescuing her from a sad end.
For her new owners, this was no ordinary financial investment. It was a labor of love:

“We grew up in Windward in the 1990s, when Windward was the mecca of economics, sailing, boatbuilding — a proud era. Around regatta time we worked on boats, dreaming of being there one day. So, acquiring American Eagle for us was our destiny, it was just a matter of time.”
Her new owners invested heavily in refits and upgrades and relaunched her as Windward Pride – the pride of Windward! The result was a slimmed-down speed machine: no doghouse, cabins, head nor anything that wasn’t absolutely necessary for achieving the all-consuming goal: speed. Of course, Carriacou being Carriacou, the launch was accompanied by much drinking of white rum and bragging from said owners, promising to deliver a sound ‘cutarse’ (beating) to all competing boats in the blue ribband event of every regatta: the round-the-island race: “Allyu watch out, we commin!!”
For this year’s regatta, once again I had the pleasure of boarding Danny Donelan’s beautiful Windward Island sloop Savvy (savvygrenada.com), although I must admit to going AWOL for some of the races! But not the big one, this would be my third circumnav, and I wasn’t going to miss it for the world. Savvy, kitted out as a working day-charter boat, was no match for the speedsters, but we had fun battling with our peers, including Beauty and Free in St. Barts.
This year’s race would be run counter-clockwise, which can often give a wild ride up Carriacou’s rambunctious east coast. But this year’s weather was disappointingly docile, with light winds and a strong onshore current, which made getting clear of the reefs at Carriacou’s southern tip a long and tacky process. Up front, Windward Pride was showing her true colors, easily outdistancing the other boats, chiefly her closest competitor, Glacier. It was a close race all the way down the leeward coast, with Glacier slightly ahead, but once clear of the reefs and tacked north, Pride passed her and inexorably pulled away, eventually winning by eleven minutes. “We coulda won by a longer margin, but we was so far in front that we just sat back and started celebrating!”
After the race, the crews gathered in Windward, thirsty, hungry and happy. And unfed — unlike in previous regattas, there was no welcoming fish broth at the Windward Community Centre (aka the disco), nor anything that remotely resembled organization. Nevertheless, Savvy’s crew celebrated our completion of another circumnav in the best way possible: by hitching a ride back to Hillsborough, eating a brilliant meal at Off-D-Hook Bar, and collapsing for a good night’s sleep!

So round one went to Windward Pride, a result that the owner of Glacier wasn’t about to accept lying down. Benson Patrice, better known as Power, owns three Windward Island sloops: Power Surge, Power Play and Glacier, and late into Saturday night he was busy making several last-minute changes for the next two days’ round-the-buoys racing. Where, as events transpired, Glacier got the sweetest kind of revenge — a triple-dose! Power hadn’t skippered Glacier in the round-the island race (“I don’t race on Saturdays”) and cited a number of tactical errors the crew made in his absence (which I shan’t reveal here).
There were no such errors on Sunday and Monday, when the Power fleet brought their A-game to the races. Skippered by Power’s brother Kenrick Patrice, Glacier sailed perfectly, winning all three races, followed home by Windward Pride each race. Power couldn’t end without commenting on the regatta organizers: “It’s really not properly organized; they get a failing grade for that. They need to get more of the boatmen involved at the planning level.”

By Monday evening the racing was over, the winners were celebrating, the losers ruing missed chances and already plotting next year’s campaign; now it’s time to party! Traditional events like donkey racing, weightlifting and musical chairs were crowd-pleasers, but sadly this year there wasn’t the one that everyone loves most: the greasy pole. A telephone pole is suspended horizontally over the water at the end of the jetty, smothered with axle grease, and a prize is given to the first person — the first brave, foolish person — to make it all the way along the pole and grab the bottle of Coke hanging from the end. Some of the pratfalls are as spectacular as they are hilarious.
Thankfully they did keep another favorite: maypole dancing — which is a lot more complicated than first appears. About a dozen young girls dance around a ten-foot pole, each holding a colored ribbon, attached to the top of the pole. They first dance clockwise, bobbing and weaving among each other, so that the coloured ribbons make a braided pattern coming down the pole. When they reach the bottom, the girls reverse direction, and unwind the ribbons until they reach back to the top of the pole — all under the watchful eyes of the ladies of the village.
Midway during the festivities there was a somber pause, for a candlelit march in honor of Grenada’s Emancipation Day, marking 183 years since the end of slavery in Grenada. Then the party started again.
That ends my report on this year’s 2023 Carriacou Regatta — well, not quite. We still need to talk about the other Carriacou Regatta. This is where things get confusing, stay with me. As everyone knows, there are two regattas in Carriacou, both of them, sensibly, held at the same time. Firstly, there’s the Carriacou Regatta, the oldest regatta in the Caribbean, held in Windward and open only to traditional Windward Island sloops. Then there’s the other regatta, held in Tyrell Bay and open to modern yachts — commonly known as the White People Regatta. So, when I say we need to talk about the other Carriacou Regatta, I’m talking about the White People Regatta, right? Wrong! There’s now a third Carriacou Regatta, held in the most unlikely of venues: Pennsylvania! As explained by Floyd Davidson, co-owner of Windward Pride:
“Me and Richard were talking, shooting the breeze about sailing and who could beat who, and it so happened that we found three identical design 15-foot boats. We bought them, gave them the same colors and names of our boats back home, and raced them for fun! The first year we did it, there was six of us, the second year about 25, and the third year, this year, we went to about 50 people — ninety-five percent of whom are from Windward! The races are held over a weekend at the Susquehanna Yacht Club on Lake Clarke, an hour’s drive from Philadelphia. We always flying the Grenada flag, it’s like a mini-regatta basically. We play country boys music, we cook, race, joke, argue — is just like if we back home!”
What an amazing achievement — who knew? That a group of 50 not just Grenadians, not just Kayaks, but from the tiny town of Windward, can bring their culture and passion for sailing to the lakeshores of Pennsylvania — bravo! To anyone from the Grenada Tourism Authority who’s reading this: Maybe these trailblazers could do with some support, huh?
On Tuesday it was time, reluctantly, to say farewell to another regatta. After a long lie-in and a hearty breakfast at the now renamed Kayak Café, but I don’t remember what the new name is and anyway it will always be Kayak Café to me, Danny, Justin and myself had a last blast on our three rented scooters, dropped them off in Tyrell Bay, then hopped aboard our nimble little speedboat, It’s Always Carib O’Clock, for the trip back to Grenada.

We did some island-hopping, taking the obligatory “They’re reading it in …” promotional photographs for my new book: Song for my Father: A West Indian Journey — to be reviewed in these pages, soon-soon.
Thus endeth the 2023 edition of the Carriacou Regatta — all three of them!