One of the best things about Tuscany is getting lost in the small roads of the territory and discovering new hidden gems. With beautiful, historic towns, you'll be immersed in an entirely unique atmosphere.
If you're not sure where to start, here you'll find a list of 38 charming small towns that boast the Bandiera Arancione. The "Orange Flag" is the tourism quality mark awarded annually by the Italian Touring Club and dedicated to small inland villages that are distinguished by landscape conservation, welcoming atmosphere, promotion of cultural heritage, quality accommodation facilities and great food.
These are the top small towns in Tuscany that you should include in your next itinerary around Tuscany.
Cutigliano stands at a height of 678 m above sea level. Some of the most beautiful sights include the town hall, the historic courthouse, the 15th century church of the Madonna di Piazza and that of St. Bartholomew.
Approaching Anghiari from the west, there's a point in the road where many first time visitors are awestruck as the entire town suddenly pops into view as your car rounds a hairpin bend.
Anghiari stands out in the wonderful landscape of Valtiberina which hasn’t been overtaken by mass tourism.
Barberino is a beautiful medieval village located in the Chianti area.
The village is contained within centuries-old walls and the town retains its original round shape, characterized by the main street connected to the two gate towers, Porta Romana and Porta Fiorentina.
Barga is a must-see when exploring northern Tuscany. This medieval town is a true hidden gem due to its location in the Tuscan-Apennine hills at 410 metres above sea level, dominated by the Pania della Croce, a mountain in the Apuan Alps.
Casale Marittimo is worth a visit as tgus area is home to some incredible natural features with hidden medieval villages where time seems to stand still.
Here, you can enjoy the fresh scent of the sea breeze as it's not far from the Tyrrhenian coast.
Lari is situated where three hilltops meet in the Pisan hills in an area that has been inhabited since Etruscan times.
The castle looms over the town centre and originally dates back to the Medieval era with most of the present structure dating back to the mid-seventeenth century.
Casciana Terme is a great spa town where you can find relaxing hydrotherapy pools, a pool used for motor rehabilitation and hot tubs with thermal water.
Just a short way from the main road between Colle and Volterra, lies the small hamlet of Casole d’Elsa. This is a lively and historic town that features a number of shops selling traditional local food products. In this area, you can find an award-winning eco accommodation, according to Legambiente.
Castelnuovo Berardenga is located in the southern area of Chianti Classico, not too far from Siena. It was built in 1366 as the stronghold of Siena given its strategic position on the border with Sienese land.
Castelnuovo Val di Cecina is a small town surrounded by oak forests. It' s not on the usual Tuscan tourist trail but that's to its advantage as you can enjoy the peaceful surroundings and experience life in an untouched rural Tuscan town.
In Castiglion Fiorentino, everything is either up or down. The peak is not drastic, with everything else perched on its side. Located between Arezzo and Cortona, it's renowned for the Etruscan archeological site and for the nine arch loggia overlooking the valley, constructed by Vasari in 1513.
The famous Tuscan writer Boccaccio, author of the Decameron and the Life of Dante, was born here. Certaldo is a great place to enjoy Tuscan food, especially in September/October during the Boccaccesca Festival. In July, don’t miss “Mercantia”, an international street art festival.
Passing through the Val di Chiana, you'll see a high but rounded, forested mountain called Cetona. At its foot, there's a town named after it. The houses surround the castle built on the summit of the hill, covered with cypresses and pines.
Chiusi is a very small town but it boasts some extraordinary necropolis, the Porsenna’s Labyrinth and the National Archaeological Museum, which houses true Etruscan treasures as well as Greek and Roman pottery. The Etruscans of Chiusi made a particular kind of pottery called Bucchero ware that's very dark and imitates metal. The lake of Chiusi (located northeast of the city) is a perfect place for those who love nature and sports. In terms of local products, don't forget to taste the DOP Terre di Siena olive oil and wine (Chianti Colli Senesi DOCG, IGT Toscana).
From its hillside position, Collodi boasts a magnificent villa and beautiful gardens, one of the most beautiful sights in Italy. Collodi hosts the most important theme park dedicated to Pinocchio and its creator, Carlo Collodi.
Fosdinovo is located about 15 km northwest of Massa and its history has been shaped by its position between the sea and mountains.
Lucignano is a small medieval village overlooking the Valdichiana, halfway between Siena and Arezzo. It's known for the Tree of Love, a true masterpiece of Gothic jewelry decorated with coral, enamel and rock crystal.
Massa Marittima is a hidden jewel perched on a hill just 50 km NNE of Grosseto, Southern Tuscany. Massa Marittima bears more resemblance to towns in Northern Tuscany, so it's quite unique in the Maremma area.
Montalcino rises on a hill covered in olive-groves and vineyards that yield the renowned Brunello wine, situated between the Ombrone and Asso Valleys.
The historic center of Montecarlo is well preserved and is famous for its wine, a magnificent fortified wall and its fortress.
On top of a high solitary hill facing Montepulciano, stands Montafollonico, a very characteristic medieval village in the municipality of Torrita di Siena.
Far from busy roads and from the usual tourist trail, it's famous for the production of Vin Santo, a traditional Tuscan sweet wine.
Montepulciano, just eleven kilometres away, is nestled between the Val D’Orcia and Val di Chiana. It's the quintessential Tuscan medieval village, boasting a green landscape of rolling hills, castle walls and ramparts, thermal springs and fine wine.
Monteriggioni is considered one of the best-preserved medieval towns in Italy and boasts magnificent exterior walls with fourteen towers on square bases with buildings inside.
This centuries-old town is important both from architectural and cultural perspectives and it has been mentioned in the Inferno of Dante Alighieri’s Divine Comedy. Nowadays, it's also famous for “Monteriggioni di torri si corona”, one of the most spectacular medieval festivals held in Tuscany.
Murlo is located in the municipality of Siena and is about 70 km south of Florence and about 20 kilometres south of Siena. The old town is intact, harmonious and well-conserved.
Peccioli has a typically Medieval appearance with narrow streets and a central piazza that's home to the Romanesque church of San Verano.
Pienza is a UNESCO World Heritage Site and is considered the “capital” of pecorino cheese given its high quality. It's derived from the fact that the cheese is made from an especially aromatic milk thanks to sheep pastures in the Val d’Orcia area.
Pitigliano has been built into the tuff rock and has a charming Jewish neighborhood. If you visit Pitigliano, don’t miss the two other tuff-built villages of Sovana and Sorano.
In the centre of Val di Cecina, you'll find the enchanting little village of Pomarance that houses the power plant of Larderello.
Radda in Chianti is a typically Tuscan town, boasting a medieval, hilltop city centre. A bell tower dominates the underlying valley, roads and alleyways with a beautifully cultivated countryside where Chianti Classico is made.
Radicofani is a small village situated on the via Francigena, the old pilgrim route running from France to Rome. The Rocca di Radicofani has towered from the top of a hill since the 11th century and dominates the surrounding territory of the Val d’Orcia, Monte Cetona and Monte Amiata.
San Casciano dei Bagni dates back to the Etruscan-Roman period and it takes its name from the famous thermal springs.
Santa Fiora is a small and charming medieval village in Mount Amiata, where stone walls, alleys, small churches and original buildings have been well preserved.
Here, you can see the old seat of local government called Palazzo Sforza Cesarini, the medieval clock tower (“Torre dell’Orologio”), the Parish churches of St. Flora and St. Lucilla, which are the most important and famous of the town’s monuments.
San Gimignano, is known as the “Manhattan of the Middle Ages” given its tall towers, It's famous all over the world and is a UNESCO site as it “represents a masterpiece of human creative genius”.
Sarteano is a charming medieval hamlet located between the Val d’Orcia and Valdichiana area. It has been inhabited since ancient times and boasts one of the most important Etruscan tombs in Tuscany.
Sorano is a town suspended in time, built on a high rock and in an extremely picturesque position that captivates all who visit it. Here, the Etruscans built a majestic necropolis.
Suvereto is a small village that dates back to the year 1000. Situated on the slopes of the hills overlooking the Costa degli Etruschi, it's a true gem that's rich in history and art, set in the green valley of the River Cornia.
Trequanda stands on a hilltop, immersed in the natural woodland with well-curated vineyards and olive groves.
This medieval village is in one of the most unspoiled areas near Siena.
In Vinci, everything is about Leonardo: his birthplace, the church where he was baptized, the museum and the library dedicated to him, even the still intact landscape in which Leonardo contemplated daily.
Volterra, a romantic city that offers visitors a glimpse of its typically medieval character, is filled with squares, palaces and towers with a romantic movie-like feel.
This mysterious hamlet allows you to take a step back in time and proved the perfect setting for the film ‘New Moon’ (Twilight Saga).
The original version of this article was written by Kinzica Sorrenti.