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Carriacou’s 34th Annual Workboat Sailing Regatta
Published in Latitudes & Attitudes,
July/August, 2000
Carriacou is a small island located in the Grenadines, but belonging to Grenada. It is an island that looks very similar to the Virgin Islands, with tall hills totally taken over with green vegetation. The main town of Hillsborough is located in a wide bay called Hillsborough, which is where most of the regatta/festival takes place.
The locals in Carriacou are very proud about their sailing heritage, many of the boats in the regatta are working sailboats that catch the fish for the island, or run cargo between the islands. “Trouble” is a refurbished whaling sailboat that is over 100 years old. All the local sailing boats are wood and most have been handcrafted on the beaches of the island. The town of Windward, located on the windward side of the island, has long been the center of boat building on the island. While we were there, we saw a large boat in the process of being built, with just the hand-carved ribs shaping the hull, ready for planking. Long boats are open wooden boats about 20-25’ long, some with gaff sails, others with battened mains. The boats in this category have bamboo masts and booms and the point of the gaff sail is propped up by another bamboo pole attached with a block and tackle near the bottom of the mast.
We were told that the race boats would be started from the beach. When we got to town the first day of the races, the boats were indeed on the beach with their mainsails up, propped up by their sand bags of ballast. We expected the boats to be pushed into the water at the start of the race; but the crews were allowed to get them into the water before the race, with the tillerman at the helm and the rest of the crew standing in waist deep water waiting to hop in at the sound of the horn. When we watched the Bahamian Family Regatta last year, the boats were lined up at anchor and at the start signal, they pulled up the anchor as fast as they could and sailed away. So we really didn’t know what to expect at this regatta.
The work boats, wooden boats about 30-35’ that we’ve seen as cargo boats in the islands, as well as fishing boats, are the only ones that started from anchor since they are too large to beach. However, we did see one boat this size that was having bottom repairs done by heeling it over in shallow water with a huge log tied to the top of the mast. One of the highlights of the regatta was being at anchor at a small island in the bay when the course took these boats right
through our anchorage. At the time, they were flying spinnakers and made for a wonderfully colorful event. Cruisers were cheering them on and the race crews were waving back happily.
The regatta has grown from a mere boat racing event started in 1965 to a 10 day festival, with games, donkey races through town, beach volleyball, events strictly for children and events for adults, such as the wet T-shirt contest and “Mr. Sexy Legs Contest”. The main street in town was blocked to traffic, speakers were set up on each block, blaring island music and people were dancing in the street. A children’s event included some of the cruiser kids and featured kid-crafted boats of recycled materials such as soda cans and bottles, plastic trash bags, etc. A model boat race featured several contestants who raced hand-made model sailboats, swimming after them to keep them on course.
The Yacht Race, was held two days and could be entered by any cruising sailboat. This event was easily won by a Beneteau, “Windbourne” from Florida. Roy and Susan on Windbourne have raced in Florida and are currently cruising through the Windward Islands.
Of course, the cruisers had to conduct their own celebratory events and planned the 2nd annual pot luck at the Carriacou Yacht Club, which was very well attended. This included a poetry/limerick contest with several entries, the winner of which received a bottle of Jack Iron. Jack Iron is an overproof local rum, about 150 proof, which I was not brave enough to try. We’ve heard rumors that ice cubes will sink in it. Several boats in the anchorage were decorated with flags to create a regatta atmosphere.
One of our favorite events during regatta festivities was the “Greasy Pole”. A long telephone pole was set up slanted over the water at an angle of about 30 degrees from the dock. The 20’ of it that was over the water had thick gooey grease on it. Two plastic ½ liter bottles of soda were tied to the end, dangling about a foot down from the pole. The trick was for the contestants to somehow get out on the end of the pole and snag one of the bottles on the way
down. Two different young men accomplished this, after numerous attempts each. Most of the participants were teenagers or younger kids who were determined to succeed, even though it looked like they hit hard on the way down.
All the cruisers in attendance had a great time and enjoyed the cultural experience in such a friendly atmosphere. As I was photographing some of the race boats, a native stopped and asked me “Don’t you just love them?” We sure did and we plan on being there for the Regatta next year, as do many of the other cruisers who were there.

Last updated by darrensmith@hotmail.com