Grosseto is the biggest town in the region, and of relatively more recent origin that the many ancient Etruscan and Roman towns in the area. It was founded in the middle ages, first mentioned in historical records in 803 as a fief of the Aldobrandeschi family, then steadily grew in importance and was consequently fought over by everybody for centuries. The Republic of Siena, Pope Clement IV, Emperor Louis IV, Alfons V of Sicily, Jacopo Piccinino the mercenary, and even the antipope Nicholas V sacked, occupied, invaded, and battled over the town until it was decimated by the Black Plague in the 14th Century.

Sienese rule finally ended in 1559, when the Holy Roman Emperor Chales V handed the territory to the Grand Dukes of Tuscany, the Medici family, who rebuilt the town, drained the nearby swamps, and built sturdy defensive fortifications and walls. It remained a small town of only a few hundred families, however, until flourishing in the 18th Century under the ruling House of Lorraine who named it the capital of the Maremma province, which it still is today. Visit the Maremma. No armies required…