English Harbour, Antigua – As Antigua prepares to hit full sail with Antigua Sailing Week just around the corner, another gem in the island’s sailing crown quietly steals the spotlight: the Antigua Classic Yacht Regatta.

Now in its 36th year, the 2025 edition promises five unforgettable days, from 16th-21st April, of elegant racing, salty tales, and vibrant shoreside festivities—all set in the island’s iconic English Harbour. Sandwiched between the world-famous RORC Caribbean 600 and Antigua Sailing Week, Classics is no less prestigious—but it is unmistakably different. This regatta isn’t just about speed and trophies. It’s about the boats themselves—their beauty, their craftsmanship, and the stories they carry.

Whether it’s the oldest boat in the fleet—the 1911, 52-foot Bristol Channel Pilot Cutter Cornubia—or the youngest, the 2013 Spirit of Tradition Harmon 60 Scotch Mist, each vessel is a living piece of maritime heritage.

The Antigua Classic Yacht Regatta was born in 1988, when a group of traditional boats, many of which had gathered to race informally at Sailing Week, decided they needed an event of their own—one that celebrated classic design, camaraderie, and the joy of sailing without the cutthroat edge.

From those humble beginnings, the regatta has grown into one of the most respected classic yacht events in the world, drawing vessels from across the Caribbean, Europe, North America, and beyond. It remains rooted in its original spirit: warm, welcoming, and dedicated to the love of beautiful boats.

Over 40 classic and modern-classic boats are expected this year, with entries from across the globe. Local pride will be on full display too, with Antiguan entries like the WISH Foundation’s 2010 Carriacou Sloop, New Moon, crewed by young, up-and-coming sailors, and Carlo Falcone’s sleek 44-foot sloop Caccia a La Volpe. From veteran yachts like Freya to Robbie Ferron’s Bunglebird, each participant contributes to the regatta’s laid-back, community-first atmosphere.

Among the returning favourites is the Anguilla-based Charm III, a Swedish-built schooner dating back to 1928.

Originally purchased by a Chicago businessman with plans to run rum during Prohibition, this salty beauty has since carved out a far more glamorous legacy. She dominated the schooner class at the 2024 Regatta with four first-place finishes, and her elegance shines off the racecourse too—Charm III is a six-time Concours d’Elegance winner and has previously claimed the Spirit of the Regatta-Seashore Trophy (2012) and the John Leader Trophy (2013).

Also back on the water is Athena, Jill Jinks’ 1988 Hinckley Sou’wester 59 from Southwest Harbor, Maine. She turned heads in 2024, surprising the veterans with her impressive performance. No longer the newcomer, she returns this year with a target on her sails—everyone’s watching to see what she’ll do next.

This year also marks the return of the crowd-favourite Single-Handed Race, set on a brand-new triangular course. With two reaching legs and a short upwind finish, it’s a challenge tailored for solo sailors who are brave enough to take the helm alone—a thrilling opening to the regatta and a true test of classic yacht seamanship.

Off the water, the dockyard transforms into a sea-lover’s playground, complete with steel bands, fire eaters, stilt walkers, and plenty of rum- fuelled storytelling. Evening sing-alongs, impromptu jam sessions, and dancing under the stars turn the historic setting into a living postcard of

Caribbean charm.

So yes, Antigua Sailing Week may get the headlines—but if you want soul, splendour, and stories shared between sailors over sea shanties and sunsets, the Antigua Classic Yacht Regatta is where you’ll find it.