In the 13th century Vertine was already in the hands of the Ricasoli, the Florentine lords of the territory, and, as a sign of its importance, it also served as their residence. It became the largest of all the fortified villages in the Chianti by extension, thus successfully resisting the Aragon invasion and avoiding the following destruction. That was also the reason why it was chosen as gubernatorial seat by the Florentine Republic . The remainder of the ancient fortifications consists of the outer walls, the stronghold, the Church of San Barolomeo , the guard tower and the small village itself, which numbers approx. 20 dwellings. In the 14th century the fortifications were restored and expanded, however without altering substantially their appearance. The painting of "Madonna della Misericordia" , originates from Vertine, and it is the most important painting of the entire Chianti. This early 14th century Siennese masterpiece depicts the majestic and unfaltering figure of the Virgin under whose protective mantle princes, clerics and laymen flock, each and everyone rendered with keen perspicacity. Of the splendid colours the deep burgundy of the Virgin's garment stands out, defining and enhancing the composition which seems to unfold like a flower. The work has been identified as the first by Simone Martini' s hand.