The history of Maremma in the Middle Ages, from the fall of the Roman empire (476 AD) up to the beginning of Renaissance is tightly connected with the names of some important families, including the Aldobrandeschis, a family of Longobard origins that in the Middle Ages possessed several important fiefs in the region, in particular those of Santa Fiora and Sovana.

The Orsini family took over the county of Sovana in the 13th century and moved the centre of power to Pitigliano. In the same period the county of Santa Fiora passed in the hands of the Sforzas. Up until the early 12th century Pisa exerted its influence over the economic life of the area, but following the definitive abandonment of the Etruscan towns in the communal age, this part of Tuscany became a satellite of Siena .

Most of the fortresses, small fortified bourgs and castles that still stand atop the hills of Maremma were built between the 11th and 14th centuries. There is Montemerano with its fortified walls, Capalbio and the Aldobrandeschi fortress, Manciano with its beautiful churches, Magliano in Toscana with its prestigious city walls and the gate of Pereta, Pitigliano with its aqueduct and the Orsini Palace, and many others. All of them are really worth a visit! Strolling in these medieval bourgs it will be like making a travel back in history.

Sassoforte, Belagaio, Montemassi, Monte Lattaia, Roccatederighi, Paganico, Arcidosso, Porrona, Monte Antico, Triana, Montepò and Scarlino are just some of the castles you could visit but the list could go on and on! Many of the castles house important works of art dating back mainly to the late Middle Ages and to Renaissance.

The Spaniards, who took the control over the coast of Maremma in the 16th century, established fortified garrisons in Orbetello, Argentario, Talamone and Piombino to protect the territory from the Ottomans. All of these fortresses overhanging the sea are well-preserved and open to the public!