Sailing takes place during normal sports sessions, in both the Michaelmas and Summer Terms, on Tuesdays, and Saturdays. On Thursdays we hold theory sessions at school, covering a number of different topics including weather, rope-work, racing rules and tactics.

The focus is on racing. Once boat speed and good starts have been mastered, sailors learn how to use their skills to out-sail the competition. More experienced racers focus on the sport of Team Racing (known by many as chess-on-water). This sport is commonly played at inter-school (and university), and hones sailing and teamwork skills.

We use Fireflies and RS Feva XLs, which places us in line with nearly every other school and university. Both boats are easy to sail (but difficult to sail well), and are the primary choice boat in UK team racing. 

We sail at Rutland Sailing Club, which is a huge, busy sailing club, based at the largest manmade reservoir in Western Europe. Rutland SC is home to four schools (Oundle, Oakham, Stamford, and Uppingham), as well as the Rutland Raiders team. The club hosted the ISAF Team Racing Worlds in 2015, and the BSDRA Easterns at National Finals in 2018. It has become one of the UK’s most prolific team racing clubs. 

Each weekend we have interschool matches, and three times a year we attend at least three day-long regional regattas which typically host at least 20 teams. At the end of the Summer Term we attend Itchenor Schools’ Week.

After leaving Oundle, many sailors have progressed to University sailing teams. We have had a number of OO university team captains, including a sailor who raced at the Team Racing Worlds.