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On December 26 took place in Montaione the traditional Live Crib, during which the inhabitants of Montaione give life to the characters of the Nativity. Along the streets of the historical centre of Montaione it has been possible to visit the hut with Jesus, Mary and Joseph, the ox and the donkey, the shepherds, the Three Wise Men and many other characters, all accompanied by traditional Christmas songs played for the occasion by Philharmonic Donizetti.
The Festival of St. Regolo in Montaione is certainly one of the most important religious events of Montaione. The Festival of St. Regolo, the patron saint of Montaione is celebrated on May 3, and when the day falls during the weekend – usually every 5 or 6 years – a feast is made even greater by involving all the village of Montaione, its citizens and the many tourists who annually come to Montaione to spend their holidays in Tuscany. During this festival, which began Saturday, May 3, is made a first procession, starting from the Church of San Regolo through the streets of the historic centre, carrying the Holy Crucifix followed by the faithful who pray and sing accompanied by the music of the Philharmonic Donizetti (the historical band of Montaione famous throughout Tuscany). Sunday May 4 the procession, accompanied by the Mayor of Montaione, has extended its route to the retirement home Villa Serena and then fall in the historic centre of Montaione and along the main streets such as Via Chiarenti, Via Cresci and the main Via Scipione Ammirato and Via Roma, and then fall in the Church of San Regolo. The Philharmonic Donizzetti then gladdened the large audience with lots of music and with the majorette, while in the evening held a fireworks show on the sky of Montaione.