Rugby School and Ampleforth College, with an adjoining monastery, are letting teenagers drink alcohol in moderation from the age of 16 at weekends.
The idea is that pupils learn to drink responsibly and do not drink too much once they leave school and enter university life.
The Benedictine monks even produce their own beer and cider made from the abbey's apple orchid, but the pupils are not allowed to drink the end result as it is deemed too strong.
Speaking to The Times newspaper, David Lambon, the first lay head of Ampleforth College, said that: "Parents worked with the school to get a suitable venue within the safety of the grounds, where pupils could eat and drink alcohol under the supervision of staff."
Students have their very own night club, the Windmill, contained on the 2,000 acre grounds, around half a mile from the school.
Mr Lambon continued: "They have food too because of licensing laws and the parents give the children smart cards that are charged remotely.
"It's very closely policed.
"In the first year of sixth form they are allowed one drink of beer or cider and in the upper sixth they can have two drinks.
"Spirits are banned."
The club is supervised by non-teaching staff.
Mr Lambon said: "We're trying to create somewhere they can let their hair down but we're all on call.
"It's a fine balance with children of that age - they need to be treated like adults and feel independent."
In the town centre Rugby School also has a club, Peter Green the head, said: "Alcohol is brought by their parents and food is served.
"They are not allowed to take bags in with them so they can't sneak in extra alcohol."
He added that it was rare for pupils to "do something wrong with alcohol."