Antigua is known among sailors as the home to premiere sailing events like the Caribbean 600 or the Antigua Classic Yacht Regatta, but, if you don’t have a classic yacht or a distance racing machine, add Antigua Sailing Week to your list. The sparkling waters, incredible scenery, and good breeze make it a first-rate sailing destination.
Drawing boats of a range of sizes and abilities from all over the world, Antigua Sailing Week supplies all the excitement and natural beauty of its better known siblings, but for a more diverse crowd. With the largest boats in the fleet measuring in at over twice the LOA of the smaller ones, it’s truly an all-encompassing race, and like many large races, Antigua Sailing Week offers an opportunity for everyday sailors to square off against the pros.
Roy Disney’s Pyewacket was in attendance as was Sailing Poland (formerly Wind Whisperer) the VO65 winner of The Ocean Race 2023. Also competing was Kialoa III, the 79-foot Dutch-flagged maxi classic that in 1975 set a Sydney Hobart Yacht Race record that stood for 21 years. On the other end of the spectrum was a host of smaller keel boats crewed by friends and families, like Tradewind 35 Cara of the South and J/30 Absolute Properties. Many also had members of Antigua’s youth sailing school aboard.
The 2024 weather was a little hit or miss during Antigua Sailing Week 2025, with some light air and some squalls, and heat typical of springtime in Antigua, but it was never too serious an impediment to the racing. The 53 boats were divided into 10 fleets, including bareboat charter, multihull, and even a flock of RS dinghies. They represented a massive 16 countries: The United States, Austria, The United Kingdom, Sint Maarten, The Netherlands, Antigua, France, Barbados, Poland, Italy, Canada, Trinidad, Switzerland, Germany, Finland, and Ireland.
Pyewacket took both line honors and first place in all seven races in the CSA 1 fleet, throwing out a first place for six points overall. The VO65s Sisi and Sailing Poland came in second and third respectively.
Racing in, and ultimately winning, CSA 2 was WaveWalker, an American-flagged Swan 58 owned by the Cullen family. For them, Antigua Sailing Week was the last event in their Caribbean sailing season before sending the boat back up to Newport for summer cruising. Woody, Carolyn, and their daughter Emma were all aboard, though two sons who often race with them couldn’t be there. The Swan 58, which they purchased 3 years ago, is a beautifully maintained racing machine that they are using to its fullest. Their main rivals of the event, the Beneteau First 47.7 Dauntless, didn’t make it easy, but WaveWalker managed to finish ahead of them by just two points.
El Ocaso, a British-flagged J122 owned by Steve Rigby and racing in the CSA 3 class, won both their class and Antigua Sailing Week’s Lord Nelson Trophy (for the CSA 2, 3 or 4 class winner with the fastest overall corrected times calculated on a time-on-distance basis). El Ocaso has now won the trophy three times, a feat only shared with Sir Peter Harrison’s Farr 115 Sojana and Larry Ellison’s Farr designed Maxi Sayonara.
“We started today in second place, so we’re really surprised to win,” says Rigby, “There are five boats that could have won this regatta. We’ve won four races and the next boat won three, so it’s been very competitive, and it really could have been anyone’s regatta, so we’re delighted, despite the boat’s success in the past. It feels like the most competitive regatta that El Ocaso has ever been in.”
Other fleet winners included Caccia Alla Volpe in CSA 4, Lee Overlay Partners III in Performance Multi, KH+P Revival in CSA Bareboat, Eira in CSA Club A, Cricket in CSA Club B, and Splice in RS Elite One Design.
Many stories of the heart of this race aren’t reflected on the scoreboard. Take for example Little Wing, whose crew included two good friends who had done Antigua Sailing Week together 20 years prior and returned this year aboard one of the only cats in the fleet for a reunion. Though their racing was cut short by a torn mainsail, the crew says they enjoyed their visit and the shoreside social aspect of the race program.
Another star of the show was the venue itself, which provided beautiful clear water against the backdrop of stunning rock formations. Throughout the week, the fleet sailed in the shadow of the Pillars of Hercules, a geological marvel carved out of the coastal cliffs over thousands of years. The water remains deep right up until the shoreline which resulted in boats tacking in dramatically close to the cliffs, truly a sight to behold. Elsewhere, Antigua’s green volcanic hills dipped down to the beaches for more stunning views.
The shoreside events are also a celebration of the sailing community, with live music and plenty of opportunities to socialize with other crews throughout the regatta. A lay day midweek provided the opportunity for sailors to do any necessary maintenance, stop by beach parties, or explore the island. Click here for our island guide.
For the full results, click here.
And for more on Antigua Sailing Week, click here.
