Truman B Takes Honours at the 2026 David Foster Memorial Catboat Race
The Cayman Catboat Club gathered on Saturday, 31 October 2026, for the annual David Foster Memorial Race, celebrating Cayman’s traditional sailing heritage, friendly competition and the longstanding support of the Foster family.
The annual David Foster Memorial Race got underway on Saturday, 31 October, bringing together Cayman’s traditional catboats and accompanying Hobie Cats for a day of sailing across the North Sound.
The race, which began at Dragon Bay and finished at Bioluminescence Bay near Kaibo, was scheduled to start at 10:00 a.m. However, a passing squall delayed proceedings, with the fleet finally setting sail shortly after 11:00 a.m.
Despite the unsettled start, conditions provided an interesting challenge for the participating crews, with shifting winds and decisions on which course to take playing an important role in the day’s results.
Truman B Leads the Catboat Fleet Home
The day’s winning catboat was Truman B, helmed by Simon Speirs, who had been entrusted with the vessel in place of Simon Boxall.
Speirs was joined by Boxall’s son, Oliver, who handled the mainsail trimming, and fellow crew member Henry, whose agility proved valuable throughout the race.
Truman B arrived at approximately 1:40 p.m., completing the course in around two hours and forty minutes.
Reflecting on the experience, Speirs expressed his appreciation for the opportunity to sail one of Cayman’s traditional vessels.
“I want to thank you all so much for the honour of being trusted to stand in for Simon Boxall and helm one of these precious boats. Perhaps the truest expression of Caymankind.”
Capt. Simon Speirs
Speirs praised Oliver’s focus on keeping the sail correctly trimmed, while noting the physical demands of balancing the vessel, even in winds of 8 to 10 knots.
With two crew members positioned along the rail and another working the weatherboard, keeping Truman B sailing flat required constant attention.
For those unfamiliar with catboat sailing, the weatherboard is an extension fitted to the windward side of the boat, allowing crew members to shift their weight farther out to counterbalance the force of the wind on the sail.
Truman B, which Speirs described as a copy of Kem’s Captain D, proved herself a competitive vessel, keeping pace with the modern Hobie Cats along portions of the course.
The crew chose a route north of Barkers, making use of favourable current before sailing close to the reef past Stingray Sandbar and reaching Rum Point, then heading south along the shoreline towards Bioluminescence Bay.
The course proved a successful choice, particularly given the shifting winds experienced by the fleet.
“Catboats are genuinely amazing craft. Thank you for the opportunity,” Speirs concluded.
A Day of Racing on the North Sound
The two accompanying Hobie Cats were reported to have reached the destination at approximately 1:15 p.m., followed by Truman B at 1:40 p.m.
The catboat Traveller unfortunately did not finish the race because of technical difficulties and was towed in at approximately 3:00 p.m.
Brac Cat reached the beach shortly afterwards at 3:03 p.m., while Whittaker Cat made its arrival after 3:23 p.m.
The day was not simply about reaching the finish line first. It was also an opportunity to bring together sailors, supporters and families who continue to keep traditional Caymanian sailing alive.
Following the racing, participants gathered at the Foster family residence in North Side for food, refreshments and fellowship.
Remembering David Foster and His Contribution
During the gathering, Cayman Catboat Club President Jerris reflected on the important role the late David Foster and his family played in supporting the Club’s development.
When the Cayman Catboat Club was formed in 1998, David Foster was among its earliest supporters, helping provide the funding and encouragement needed to establish the organisation.
Jerris recalled that Foster had originally owned a traditional round-bottom catboat which the Club regularly used and cared for. Recognising the Club’s dedication to its preservation, Foster eventually entrusted the vessel to the organisation.
His support extended beyond the boats themselves, helping establish a lasting relationship between the Foster family and the Club.
Following Hurricane Ivan in 2004, when the Club lost its clubhouse, John Michael Foster was among the first to offer assistance, providing a boardroom where members could continue meeting.
Jerris also acknowledged the longstanding encouragement of Mrs. Chi Chi Foster, sharing a light-hearted memory of an occasion when David Foster went sailing in a catboat while dressed for an evening out, leaving Chi Chi, who was also dressed for the occasion, waiting ashore.
The story brought a personal touch to the gathering and reflected the close relationship the Foster family has maintained with the Club over the years.
Looking Ahead to the Future of the Race
Originally known as the Foster’s Food Fair Race, the event was later renamed the David Foster Memorial Race in recognition of his contributions.
During his remarks, Jerris spoke about the next chapter for the event, with responsibility for its continued stewardship transitioning to the Foster family.
He also recalled developing a dedicated race logo in 2009, which is intended to become a consistent part of the event’s identity, including future commemorative shirts and promotional materials.
Looking ahead, the Club is considering making the David Foster Memorial Race the final points-scoring event of its annual Catboat Championship Cup.
This would allow the racing season to conclude in October, followed by an annual championship prize-giving in November.
The proposal is expected to be discussed further at an upcoming Club meeting.
Keeping Cayman’s Maritime Heritage Alive
The David Foster Memorial Race remains an important part of the Cayman Catboat Club’s calendar, combining the competitive spirit of traditional sailing with an appreciation for the people who have helped preserve these vessels and the skills needed to sail them.
The Club extends its appreciation to the Foster family for their continued hospitality and support, and to the skippers, crews, volunteers and supporters who contributed to the day’s activities.
More than a competition, the annual race serves as a reminder that Cayman’s maritime heritage continues to live through the people who build, maintain, sail and share these remarkable boats.
