Sailing is available throughout the year and is run in conjunction with Sherborne Girls. Sailing takes place at the local Sutton Bingham Reservoir and is the largest school sailing progamme in the geographical area.
There is, subject to demand, the facility for teaching pupils with no experience and indeed some such pupils have progressed to representing the School in matches. Pupils have access to a variety of boats with a matched fleet of six 420s supplemented by Fireflies, Lasers, Fevas and Picos. There is a full programme of coaching and team racing against schools throughout the year, in addition to entries to British Schools Dinghy Racing Association (BSDRA) competitions. Boys and girls from both the junior and senior parts of the School may compete either as a combined team, or separately as a junior and senior team.
The School enters between two and four boats for the Schools Fleet Racing Championship every year. In the past, Sherborne has excelled posting a first and a second place in this highly competitive event.
Boys in the Fifth Form are encouraged to apply for the Andrew Yorke Award, which covers all the costs for them to complete the full RYA Dinghy Instructor's course.