COWES High School’s headteacher has announced he is to retire ahead of £36-million plans to transform the school.
Medina High School is also to lose its headteacher, Richard Williams, who is to become principal of an academy school in Kent.
David Snashall, head at Cowes for the past seven years, said the timing of his departure, at the end of this term, was linked to the school re-organisation.
Under the changes planned for Island schools, Cowes will undergo a massive rebuilding programme, becoming a pathfinder school, with links to Southampton University.
The body appointed to run the school, Cowes Pathfinder Partnership (CPP), was this week expected to begin searching for a principal to take over the running of the school in 2011.
An acting head will be appointed to run the school until the CPP-appointed principal takes over.
"I am disappointed I will not be able to see the fruition of all the work we have put in to make Cowes a successful school in relevant terms.
"But now is the time to pass it on," said Mr Snashall, who said he would no longer teach but would work in education consultancy.
Mr Williams, who has been head of Medina for seven years, said his decision to leave no later than Easter, was also influenced by re-organisation.
"I do not feel I am being pushed out by the re-organisation. I would not disagree that the school has been transformed and a new leadership should come in and see where the school is now as the start point and take it forward," said Mr Williams, who will not leave until an acting head has been appointed.
He said the school had changed from one which was undersubscribed and unpopular, to the only high school which would be oversubscribed this year.