BOATS WITH LIVES OF THEIR OWN It is this sense of belonging that gives the event its particular texture. These are not museum pieces. They are working vessels – maintained, repaired, sailed hard and cared for with a level of attention that borders, at times, on devotion. The distinction between restoration and preservation is not always clear-cut, but it is always deliberate. Every decision – what to replace, what to retain, what to improve – is part of an ongoing conversation between past and present. More than 30 yachts are expected for 2026, combining international pedigree with strong local representation. Among the local boats, New Moon, a 31-foot Carriacou sloop, stands out for both her vivid blue-and-orange livery and her purpose. Crewed by young Antiguan sailors, she is not only a regular presence on the podium but also a working training platform. Young sailors can often be seen barefoot on deck, moving without instruction during manoeuvres that feel almost instinctive. Regular podium finishes and multiple Concours d’Elegance awards have made her both competitive and emblematic of the regatta’s spirit. Returning favourites include Charm III, a Swedish schooner from 1928 now based in Anguilla. Once intended for rumrunning during Prohibition, she has since built a more polished legacy, including overall victory in 2025. Athena, with her flirty spinnaker, a 1988 Hinckley Sou’wester 59, also returns for her third regatta, her recent performances suggesting a boat – and crew – to be reckoned with. Among the larger yachts, Ashanti IV has a special place. Built in Bremen in 1954 as the private yacht of the shipyard owner Ernst Burmester, the 114-foot steel schooner was once Germany’s largest yacht and remains a commanding presence on the racecourse. Under the ownership of a German businessman, she has secured multiple class wins, including overall victory in 2018. It was aboard Ashanti IV, over drinks at the saloon table with her then captain Uli Prüsse and charts still open, that the idea for the Antigua Classics Regatta was first conceived. Earlier along the timeline, Adventurer offers her own perspective. Alexander Child’s gaff-rigged schooner began life as Malabar VI, designed by the renowned naval architect John Alden. Measuring 52 feet on deck and 65 feet overall, she was built by the Hodgdon Brothers in Boothbay, Maine in 1925. Seven sister ships were constructed to this design, but Adventurer is the only one that remains – a rare survivor from a celebrated era of American yacht design. Few yachts carry a story as poignant as Guiding Light, back after a long hiatus. Launched in 1936, she was painstakingly restored by the late Roy Boughton after he purchased her in 1993, much of the work done by hand, often in silence in a Southampton yard. After years of sailing in the United Kingdom, he brought her across the Atlantic to the Caribbean, where she became a familiar presence at the regatta, winning her class and the Concours d’Elegance in 2010. Her history includes both near loss – she was once rescued from sinking during the 2015 Parade of Classics – and personal tragedy. Boughton was lost at sea off St Lucia in 2018. Now restored once more by Alasdair and Gill Maclean, Guiding Light returns as both vessel and legacy. Elsewhere in the fleet, the schooner Kairos returns after an absence since 2017, while Magnolia, a 56-foot schooner built in Maine, makes her debut. Zig Zag, an Oyster 82, adds a more contemporary note within the classic framework. The 72-foot ketch Ticonderoga of Greenwich also returns, while Jabberwonk, Olympic gold medallist Poul Jensen’s Dragon, demonstrates that classic design and competitive sailing remain closely aligned. A more recent chapter is represented by Maiden, the 58foot ocean racing yacht associated with Tracy Edwards and her pioneering all-female crews. Her presence connects the regatta’s historical focus with more contemporary milestones, including winning the 2024 Ocean Globe Race, with fast-becoming-legendary Antiguan sailor Junella King among the crew. RACING, QUIETLY INTENSE Racing begins with the Single-Handed Race, a measured but demanding test of seamanship. Two reaching legs and a short upwind finish provide a precise opening to the regatta. You notice the silence between manoeuvres more than the noise – the pause after a sail fills, the moment a boat settles onto her line. To watch Kalle Ebner, captain of Ashanti IV (winner Single-Handed 2018), manoeuvre the 114-foot yacht alone is a masterclass in seamanship. Across the following days, racing unfolds without urgency but not without intensity. These boats are not indifferent to competition. They are sailed to win. But the margins are different, and so is the experience. You see it in the way crews pause before a tack, in the extra second taken to feel the wind rather than simply read it. 22 read more
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