Countdown to Antigua Sailing Week 2026

For more than half a century, Antigua Sailing Week has been one of the Caribbean’s most recognizable sailing events. For racers, in recent years, it has meant tight courses off the south coast, competitive fleets, and long afternoons dissecting starts over cold drinks. For Antigua, it has meant full anchorages, busy docks, and a global spotlight on the island’s sailing culture.

So when word began to circulate that Antigua Sailing Week would be changing its format in 2026, it was natural for eyebrows to rise. Change, especially to something so deeply woven into Caribbean sailing history, invites questions. Why now? Who is it for? And does “change” mean leaving the past behind?

The short answer is no. What’s happening behind Antigua Sailing Week is not a departure—it’s an evolution shaped by the realities of modern sailing, shifting demographics, and the simple truth that how people experience boats, events, and time on the water has changed.

As Antigua Sailing Week ushers in its refreshed format — blending relaxed racing with a cruising rally spirit — it’s the sailors themselves who bring the concept to life. From lifelong Caribbean campaigners and multigenerational family teams to first-time international competitors chasing sunshine and challenge, this year’s fleet reflects the diversity and energy that define racing in Antigua. If you have been considering taking part this year, there is still ample time to prepare - so consider this your reminder to enter before entry fees increase on March 7.

With less than 7 weeks before the start of the event, we would like to spotlight some of these enthusiastic teams embracing the adventure, camaraderie, and competitive edge of this exciting new chapter.

While he may be among the older crew in this year’s Antigua Sailing Week fleet, Patrick Holloran, from Essex in the UK and who turns 80 in March, will be racing Caipirinha, his Beneteau First 40.7 in the 57th Antigua Sailing Week regatta. The boat has lived in the Caribbean since it was purchased in 2000 and Holloran bought it in 2006 after his kids inspired him to race in Antigua following their first trip to the island in 2003.

SHORESIDE & SPECTATORS

For those not racing or cruising around the island, in addition to joining the sailors at the scheduled post race parties around the island, there are other exciting ways to experience the spectacle and be a part of Antigua Sailing Week 2026.

On Tuesday April 21 sailors, spectators and visiting guests are all welcome to join in a night of irie vibes featuring Caribbean artist Luciano the Messenjah at the 15th edition of Reggae in the Park.

Luciano’s music is deeply rooted in faith, unity, resilience, and social awareness. His timeless anthem It’s Me Again Jah became an international reggae staple, cementing his reputation as an artist whose message transcends borders and generations and the Antiguas best reggae talent Zambai & Friends, Bless Eye will be backed by The Climaxx Band. 

On Saturday April 25th, everyone is welcome to experience the vibrant day-long celebration Riddim & Tides. Inspired by the Caribbean’s growing culture of on-the-water lifestyle events, Riddim & Tides blends sailing, soca music, beach vibes, and island tastes into one unforgettable Saturday. This is a chance for the Antigua Sailing Week participants to enjoy an Antiguan social immersion on day three of their circumnavigation.