Founded in 1313 by Bernardo Tolomei, a jurist from one of the most outstanding families in Siena, the monastery of Monte Oliveto Maggiore is Benedictine in practice. Benedictine monks are the most mainstream, practicing "peace, prayer and work," while living in autonomous communities with their own local government.
Monte Oliveto Maggiore owned most of the land in the Siena region, so having its own private government would come in handy when dealing with such riches. Fortunately, Bernardo Tolomei was a jurist, leaving the monastery in a very lucrative state by the time he died.
- Monte Oliveto Maggiore could be translated as "the greater Olivetan mountain," to set it apart from other Olivetan monasteries.