Here is a Tuscan travel dream list with 10 small towns in Tuscany that are worth a visit. These are the places that we want to discover or to see again, because visiting the Tuscan hidden gems always seems like the first time. Enjoy, come up with your own list and try to reach them all!
Arezzo and surroundings: Castiglion Fiorentino
Castiglion Fiorentino is a small, walled city located 342m above sea level near Arezzo in eastern Tuscany, also situated close to Cortona. The earliest trace of Castiglione dates to the 10th century and we know that, at the time, it was an estate of the Marquis of Monte Santa Maria. It has had an eventful history, characterized by various conquests, eventually becoming part of the Grand Duchy of Tuscany ruled by the Medici family. Numerous architectural structures, such as the massive town walls and the impressive fortified complex of the Cassero, highlight the town’s past strategic importance. Today, in light of recent archaeological discoveries, Castiglion Fiorentino has also achieved distinction as an important Etruscan centre in the Valdichiana area. The main sights include the Church of Sant'Angelo al Cassero, where, during the restoration, different alignments of the walls were discovered in the crypt, characterized by large, square blocks belonging to the Etruscan wall circle (4th century BCE). Other sights are Piazzale del Cassero, where an excavation has unearthed a sanctuary; castle walls; the Etruscan gate (4th century BCE); the Casseretto; the Palazzo Pretorio and the Archaeological Museum.
Florence and surroundings: Pontassieve
Pontassieve takes its name from the bridge that connects Florence and the Val di Sieve (“ponte” means bridge and “Sieve” is the name of the river). Pontassieve is located about 14 kilometres east of Florence, not far from Fiesole, and was immediately viewed as an area of enormous strategic importance, which explains why the town was fortified. The most important period of growth for the town was in the eighteenth century under the rule of the Grand Duke Lorena, when, thanks to two new roads, both trade and population increased. During World War II, Pontassieve, due to its importance as a railway junction, suffered substantial damage and was repeatedly bombed by Allied planes, which destroyed it almost entirely. Today, the town's aspect is due to the post war reconstruction, even though the town has kept its original medieval look in the town centre. There are many churches and parish churches worth visiting as well as beautiful surrounding countryside of olive groves and vineyards.
Grosseto and surroundings: Sovana
Sovana is a small town situated in southern Tuscany, near to Sorano. It is known for being one of the major Etruscan centre, a medieval and Renaissance town and episcopal seat. The village is included in the list of most beautiful towns in Italy. The main sights include the Rocca Aldobrandesca, probably built on top of a pre-existing Etruscan/Roman fortress; the Palazzo Pretorio (13th-15th centuries); the Romanesque church of Santa Maria Annunziata (12th-13th centuries); the St. Peter Cathedral, built in the 11th-12th centuries on top of an older 8th-century building in Romanesque style decoration with biblical scenes and a curious relief of a two-tailed mermaid; the Church of San Mamiliano, maybe the oldest in the village.
Livorno and surroundings: Sassetta
Sassetta is located about 50 kilometres southeast of Livorno, inland between Cecina and Piombino. Mentioned in documents dating to the 11th and 12th centuries, it is surrounded by chestnut woods and Mediterranean scrubland. In the Museo del Bosco ('Woodland Museum'), an interesting themed museum of local daily life and professions, like chestnut and blackberry picking and ancient coal merchants. The park in Poggio Neri, a place of amazing beauty, is an oasis of uncontaminated nature. Among the places of interest we can include the remains of the Orlandi castle in the town centre, the building Palazzo Ramirez de Montalvo, the Church of St. Andrew and the Oratorio di San Rocco. Going south, towards the river Cornia, you can find a trekking route in a wooded area of natural interest, which includes Mount Calvi and the hills north of Castagneto Carducci.
Lucca and surroundings: Massaciuccoli
The village of Massaciuccoli is situated in the heart of the Versilia area in the municipality of Massarosa and preserves traces of human presence since prehistoric times. Olive trees, the Massaciuccoli Lake and many remains of the Roman era characterize this area. The Archaeological Area of “Roman Massaciuccoli” boasts a perfectly preserved mosaic, two leading complexes from the Imperial Roman era and area called “Le Terme” (the baths). In recent years, the archaeological site has been renovated with a museum featuring small relics commonly used in Roman times such as jewellery, vases, coins, etc. More here http://www.turismo.intoscana.it/allthingstuscany/tuscanyarts/archaeological-area-massaciuccoli/ The area of the lake is very appealing, too, and can be considered the wild side of Versilia, with the largest natural lake in Tuscany. The Oasis of Massaciuccoli is a protected natural area that aims to preserve the local fauna and flora. Here you can find long wooden trails passing through the marshes, as well as special sighting points where you can watch out for birds.
Massa Carrara and surroundings: Montignoso
Situated 3 kilometres from Massa, Montignoso does not have a town centre as such, but each hamlet is independent. The old feudal castle of Aginulf, now Aghinolfi Castle, was the first modern settlement of the town and a strategic point of military observation. The municipality of Montignoso, on the Gothic Line, suffered numerous devastations during the last war and was awarded the Gold Medal for Civil Valour. The main sights include the already mentioned Castello Aghinolfi, constantly fought over by the military forces of Pisa, Genoa and Lucca; Villa Shift Giorgini, a splendid nineteenth-century residence and the current seat of the Municipal Authorities; the Church of St. Eustace (15th century) and the Parish Church of St. Vito and St. Modesto (12th century).
Pisa and surroundings: Lari
Lari is a hamlet in the municipality of Casciana Terme Lari, in the province of Pisa and is located about 25 kilometres southeast of Pisa, on a hilltop. The town was awarded with the Orange Flag by the Italian Touring Club as one of the most interesting small towns in Italy. The small town of Lari has been inhabited since Etruscan times. The castle, in a dominant position overlooking the town centre, originally dates to the Middle Ages, but most of the present structure dates back to the mid-seventeenth century. A defensive wall with three entrances protects the castle: the Porta Fiorentina, the Porta Pisana and the Porta Volterrana. The town’s important monuments include the fifteenth-century San Leonardo and Santa Maria Assunta Church.
Pistoia and surroundings: Abetone
Abetone is located in the higher Pistoia Mountains, near the border with Emilia-Romagna. Abetone is known as a holiday resort in the summer and winter and it is considered the most important ski resort in the Apennines. In the nineteenth century, Abetone was a destination for elite tourism and has over 50 kilometres of ski slopes in four beautiful valleys: the valley of Sestaione, the valley of Lima, the downstream of Scoltenna and the Val di Luce. Abetone has been frequented by tourists since the mid-nineteenth century and by skiing pioneers from the beginning of the 20th century, with a peak in tourism in the 1930s. Abetone is important mainly from a naturalistic point of view.
Prato and surroundings: Montepiano
Montepiano is one of the most beautiful tourist resorts in the Tuscan-Emilian Apennines in the municipality of Vernio, and it is located on a plain where the River Setta flows. Mountains, dense forests and sunny meadows surround it. Its territory borders the Tuscan Protected Area of Local Interest "Alta Carigiola e Monte delle Scalette" and the Emilian "Parco dei Laghi". The centre of the village, located along the regional road number 325, consists in a nineteenth-century village with bars, hotels, restaurants and shops. Montepiano is the ideal destination for anyone looking to escape the hustle and bustle of the city. One of the main sights is Saint Mary Abbey built around the 1095 and a beautiful lake.
Siena and surroundings: Radicondoli
25 kilometres southwest of Siena, in the metal-bearing hills that overshadow the Val di Cecina, lies Radicondoli, a walled town perched on a hilltop with panoramic views of the Tuscan countryside. There was human presence here even in Etruscan-Roman times, but the subsequent medieval installation erased it completely. In this town you can admire the Elci castle, the convent of St. Francis, the parish of St. Simon, the castle of Radicondoli, the castle of Belforte and "the Energies of the Territory" museum.