In the Maremma plains and low hills, the town of Roccastrada is north of Grosseto and south of Siena. It is midway between the stunning Val d'Orcia and the Mediterranean seacoast at Follonica and Punta Ala. While the town of 8,800 people is located at 283 meters above sea level, the peaks beyond it rise -Monte Alto is 797 meters and Sassoforte is 787 meters above sea level. The area offers a rich diversity of landscapes (and seascapes!) in a short distance. It has a train station along the Grosseto - Siena line.
The Middle Ages brought the powerful Aldobrandeschi family but Siena conquered the territory and controlled the zone until the 1500s. It was valued for the copper and silver mining in the hills. With the fall of the Siena Republic in 1555, the territory entered under the dominion of the Grand Duchy of Tuscany.
There are a few frazioni hamlets under the jurisdiction of Roccastrada. They are charming villages you should also seek out: Ribolla, Roccatederighi; Sassofortino; Sticciano; Torniella; and Piloni.
What to see in the town and surrounding area? In town, the main church of San Niccolo dates to 1283 and holds two impressive frescoes - one of the Annunciation, and a Madonna with Child. The tall clock tower, standing proudly amidst the medieval buildings, and the Teatro dei Concordi theater are must sees in town. Also, don't miss the Wine Museum (Museo delle Vite e del Vino), located below the clock tower. With its underground rock-hewn rooms and panoramic terrace over the Maremma, it is worth a visit.
In the country between Roccastrada and Montemassi, the mystic-like remains of the Abbey of San Salvatore are intriguing; the underground crypt seems lost in time, like something you'd see in an Indiana Jones movie. It is worth seeking it out, in localita' Casacce.
Montemassi is a dramatic sight on the hill, crowned by the remains of its castle rising on the top. The village was immortalized in a fresco in the Palazzo Pubblico in Siena, so if you visit that art city, keep your eyes open for the painting depicting the town!
The ruins of the castle, Castello Sassoforte, are evocative and a nice walk from Sassofortino. While you're there, stop in at the Parco delle Forme di Pietra, a stone sculpture park.
Riserva Naturale Farma is a beautiful nature reserve along the Farma River valley, with natural pools and waterfalls, amidst forests of beech, sycamore and birch, and some unusual canyon-like formations, too.
Parco Tecnologico Archeologico delle Colline Metallifere Grossetane is a long name for a park dedicated to the biodiversity, rocks and minerals that are found there - it combines mining history, geology, archeology and nature.
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Explore nearby towns
The hamlet of Montemassi is a dramatic sight with its dominating castle settled on the rock above the clustered buildings of the town.
In the heart of southern Tuscany between Siena and Grosseto, Civitella Paganico clusters on a hill above a wavy landscape.
In the hills of Tuscany's Maremma district, the town of Ribolla is a modern addition to the hamlets of the area.