Reggie Benjamin grew up on Karsten De Hoop farm in De Doorns and matriculated in 2022. He joined the Waitrose Foundation’s Youth Development Programme in 2023, starting his journey at The Pines farm before becoming a Sailing Instructor at The Little Optimist Sailing Academy.

Now based in Heideveld, Cape Town, Reggie works at the academy’s headquarters at the V&A Waterfront. In 2025, he will be part of an exciting new pilot project with the 9 Miles Project, launching the first Sailing Therapy programme at the Strandfontein tidal pool. Reggie’s connection with the Waitrose Foundation began in primary school, where he participated in the ATKV group and youth choir and even met England cricket captain Alastair Cook during a visit in 2016.

After reconnecting with the Foundation post-high school, he completed programmes like the School of Entrepreneurship and the Laureus YES Programme, gaining confidence and leadership skills that led him to speak on public panels—something he once thought impossible. Reggie is deeply grateful to the Waitrose Foundation for the mentorship, knowledge, and personal growth it has offered, helping him turn perceived weaknesses into strengths and empowering him to inspire others through the sport of sailing.