Travel Guide: The Fairy-Tale Villages in Tuscany Full of Medieval History

In Tuscany, the scenic landscapes play the songs of enchanting beauty stuck in time. The hilly villages transcend the ages of history in their lovely streets. Tuscany creates magic with the flute of its charming villages.

The rolling hills are filled with breathtaking views, especially in Val d’Orcia, which is listed as UNESCO World Heritage Site. Tuscany is the land where poetry takes the principal note. Numerous artists and poets have been inspired by its gracious existence.

Between the tiny cypress trees, stone houses and ancient castles, Tuscany lives the magical moments. Under the promising sky, Tuscany holds the dream that never sleeps.

The Fairy-Tale Villages in Chianti Region

The Chianti is situated between Sienne and Florence among picturesque vineyards and fantastic images. This famous region defines the classical countryside of Tuscany with the successful wine tour as the best option.  The wonder of green hills intertwines with the magic of olive groves.

Scenic views of the vineyards in the Chianti region in Tuscany
Scenic views of the vineyards in the Chianti region in Tuscany- Credit:

Doing a road trip along the Chianti region is the most rewarding choice to discover the landscape. The Chiantigiana route offers wonderful hidden corners and pleasant photo opportunities. Taking a bus from Florence or Sienne matches the roads, but freedom comes with the proper car.

Castellina in Chianti

Castellina in Chianti is one of the top destinations in the region, alluring with its medieval charm. The ancient walls embrace the village and the lovely fort shines like the crown. Now it holds significant traces from the Bronze Age, Etruscan and Hellenistic times. A small Etruscan museum is situated in this ancient fortress from the 15th century.

Aerial view of the stone houses in Castellina in Chianti
Aerial view of the stone houses in Castellina in Chianti- Credit:

One long street is a vibrant gathering of several small shops and cafe bars. The fascinating Via delle Volte merges with the ancient walls while shaping the covering tunnels. This charming street gives several spots for romantic meals.

Tasting wine is one of the classical activities in Castellina within one of the various enotches.

Castellina creates “Lega del Chianti“ together with Radda and Gaiole in Chianti, which had an important defensive role in the past.

Greve in Chianti

Greve in Chianti is a pretty little town located 30 km from Florence. The triangular-shaped square dominates the centre with classical loggia in view. The famous Italian explorer Giovanni da Verrazzano from Greve holds a memory dedicated to the statue here.

Greve in Chianti is a place of markets and they’re especially popular every Saturday. The antique market on Easter Monday is a true sign of the place. Several festivals have a fantastic ambience in the main square of Greve. The most popular are the music Spring festival and Chianti Classico Exposition.

The arched loggia hosts various artisan and local products on sale at the colourful Piazza Matteotti.

Greve got the name by the small river that flows through it. Few castles decorate the streets of Greve, while the castle of Verrazzano is a beautiful hilly villa.

Radda in Chianti

Radda in Chianti is a picture-perfect hill town in Tuscany embraced by walls. The narrow streets shine on the medieval appearance of this ancient village from the 9th century.

The history of Radda traces back all the way to the Etruscans. Once the capital of Chianti, Radda can thank this to the central location between the Chianti hills. The Palazzo del Podesta’ inside the walls enjoys the beautiful decor and medieval feel of the 16th century. The Museum of Sacred Art inside the Franciscan Monastery is one among the similar ones in the Chianti region.

Pretty stone houses of the hilltop village Radda in Chianti
Pretty stone houses of the hilltop village Radda in Chianti- Credit:

The Ice House of the Grand Duke is an interesting building created to store snow and turn it into ice.

Radda is rich with cultural events that attract visitors to cobblestone magic.


Montefioralle lies in close proximity to Greve in Chianti, another fortified wonder of Tuscany. This charming village enchants by the tower houses full of medieval spirit.

Montefioralle was the birthplace of the famous Italian explorer Amerigo Vespucci. His family lived in the castle of Montefioralle.

Fascinating artworks hold the shine in the Church of Santo Stefano.

Embraced by the picturesque vineyards and olive groves, Montefioralle is the perfect place to enjoy a glass or two.


One of the prettiest villages in Tuscany, Monteriggioni, is embraced by stone walls with defensive towers. It shines majestically on the hill Monte Ala, while the impressive landscape around just confirms its glory.

Located about 20 km from Siena, Monteriggioni spells its medieval magic from 1213 when the fortress was built, even before. It has been an admiration to many artists and poets, including Dante Alighieri.

Pretty walled town of Monteraggioni in Chianti, Tuscany
Pretty walled town of Monteraggioni in Chianti, Tuscany- Credit:

The castle is still well preserved as its original purpose had a defensive role against Florence.

The surrounding villages carry a pure enchantment, like Abbadia Isola, Valdelsa or Val di Cecina. The legendary Via Francigena traces numerous nature trails, including the one from San Gimignano to Monteriggioni.

Several cultural events vibrate the life of the village. The medieval festival is in July and one of the oldest cultural festival in Italy. Slow Travel Fest celebrates the glory of outdoor travellers in June, September and October.

Val D’Orcia- The Scenic Landscape South of Siena

Val d’Orcia is a fairy-tale valley which stretches from the south of Siena to the volcanic mountains of Monte Amiata. It got its name by the river that flows through the heart of the valley. Val d’Orcia belongs to the six UNESCO World Heritage Sites in Tuscany.

Typical scenery of Val d'Orcia with rolling hills and cypresses
Typical scenery of Val d’Orcia with rolling hills and cypresses- Credit:

This dreamy landscape will just enchant with the rolling hills that seem to come out of the paintings. The immense beauty spreads its wings here from the astonishing castles, ancient villages, fabulous cypress trees and many thermal hot springs. Bagni di San Filippo offers the natural pools at the palm of the forest.


The historical jewel of Tuscany, Montalcino, is the home to a large medieval castle. The recognizable sign of Montalcino is Brunello wine, the famous red wine.

Piazza di Popolo marvels within the vibrant centre, which transfers to the scenic views at the top of the fortress. The fortress hosts the popular Jazz & Wine Festival in July.

Museo Civico e Dioceziano is the archeological treasure of Montalcino, holding fascinating artworks. Museo del Vetro (Glass Museum) clusters the history of glass making from Egyptian to Roman times and Venetian marvels.

Sant’Antimo Abbey is the charming Romanesque church, 10 minutes from Montalcino.

The colourful streets are made to wander along the pretty cafe bars, crafty shops and restaurants.


The hilly views of Montepulciano enchant the visitors from the first moment. The soft valley of Val d’Orcia spreads so perfectly from the balconies of Montepulciano.

Elegant palaces and charming squares hold the beauty of Montepulciano. The walls that surround Montepulciano transcend the Renaissance style and romantic spirit.

The Vino Nobile enriches Montepulciano with its local taste and few wine cellars are worth to visit. Piazza Grande collects all the medieval treasures, like the clock tower of Palazzo Communale, the historical well or the unfinished Duomo. Piazza Grande is the point of cultural events with artistic designs in the style of its author, Antonio da Sangallo.

Chianciano Terme and Lake Trasimeno make an easy trip from Montepulciano.


A typical Tuscanian town ornates the hilly images and cobblestone streets inside the walls. Pop Pius II created his Renaissance vision on the utopian principles. This vision includes the Cathedral, Piccolomini Palace, the Town Hall and a lovely central square.

The Cathedral del’Assunta is decorated by elegant paintings. Palazzo Piccolomini delights with the impressive views from the garden loggia. That’s why the romantic movie Romeo and Juliet had some scenes in this place.

Fabulous view from the main terrace of Pienza, Val d'Orcia
Fabulous view from the main terrace of Pienza, Val d’Orcia- Credit:

Pienza owes its praise to the delicious cheese Pecorino made from sheep’s milk. Lovely shops are rich with outstanding varieties of pecorino and other local products. In September, a famous festival is dedicated to pecorino cheese, Fiera del Cacio.

San Quirico d’Orcia

San Quirico d’Orcia is a stunning village of Etruscan origins and idyllic atmosphere. This walled village embraces the main street of Dante Alighieri, which leads to the church Collegiata di San Quircio. Together with the Church of Santa Maria Assunta, the medieval grace invites.

Palazzo Chiggi hosts elegant frescoes from the 17th century.

The Renaissance gardens of Horti Leoni are the delight of the village, covering the symmetrical shape.

The famous cypress trees of San Quirico d’Orcia are the symbol of Tuscany.

Bagno Vignoni

Bagno Vignoni is a charming village near San Quirico d’Orcia. It holds a large pool with thermal spring water just on the main square.

Bagno Vignoni has a reputation as a spa town though tiny in size. Several hotels are located here as the main pool is not for bathing. It’s a lovely place to absorb the vibe of the honey-coloured houses.

Main square of Bagno Vignoni with the thermal spring water
Main square of Bagno Vignoni with the thermal spring water- Credit:

From Parco dei Mullini, just outside the main Plazza, you can enjoy the view of Monte Amiata and the ancient structure of the canals.

Arrezo Region

On the eastern wing of Tuscany lies the Arrezo region. Taking the crown with the medieval city of Arrezo, this area is a hidden gem of Tuscany. It’s surrounded by the mountains of Casentino and Pratomagno in the valleys between the Tiber and Chiana rivers.

Arrezo town is one of the oldest Etruscan places in Italy and has a strong medieval touch.


This small medieval town is situated 30 km from Arrezo and picturesquely stands on the hill. Known by many artisan shops, wandering around is pretty magical. Wood, textiles and ceramics are the most common crafts in this lovely place. Many workshops hold the historic touch and Popular Tradition Museum adds the artistic note.

Aerial view of the walled village Alghiari in Arezzo region
Aerial view of the walled village Alghiari in Arezzo region- Credit:

Anghiari celebrates art of craft with a traditional exposition in April.

Several palaces enchant the historic touch of the place. The ancient walls gently shape the town.


The fabulous views from Cortona spread up to the soft valleys and even to the lake Trasimeno. The narrow streets charmingly touch the Etruscan walls with the Basilica of Santa Margherita popping up.

Located 30 km from Arrezo, Cortona impressively touches the heritage of several museums and palaces. Diocesam Museum holds the main role with the panel painting by Beato Angelico.

The Tuscan Sun Festival is a popular event during summer giving praise to the art.

The Fairy-Tale Villages Near Pisa & Lucca

Pisa and Lucca stand under the protection of the mighty Appuan Alps. Rolling hills near Pisa create a fascinating landscape in the valley of the river Arno. The relaxing holidays surrounded by lovely nature is the choice in the spa towns like San Giuliano Terme, Montecatini Terme, Cascina or Uliveto.

Charming hilltop village of Barga with the mountain background of Appuan Alps
Charming hilltop village of Barga with the mountain background of the Apuan Alps- Credit:


Barga is a beautiful hiltop town set in the heart of the Apuan Alps, near Garfagnana. Located about an hour from Lucca, Barga is a heavenly resort with a mountain background.

The most scenic views in Barga hide themselves near the Cathedral, a beautiful Romanesque building. The town filled with palaces speaks about its rich history. In particular, Loggia dei Mercanti represents the past of the market town.

Teatro dei Differenti and Casa Pascoli are the most significant buildings where the cultural heritage opens the doors of Barga.

Casa Pascoli is a museum dedicated to the most famous citizen, Giovanni Pascoli. The garden inside is the place of many musical, artistic and children’s events.


Volterra is a hidden gem in the Cecina valley with strong Etruscan traces. The rich offers from the museums include the Etruscan Museum, the Museum of Sacred Art or the Eco-museum of Alabaster. Alabaster is the typical product of Volterra, dedicated to the vast palette of the local arts and crafts.

Six walled gates protect the entrance of this stunning village. The main square, Piazza dei Priori, is a specially charming place to enjoy a cafe.

The lovely cobblestone streets are filled with flowers and just outside of the town is the Roman Theatre.

The Fairy Tale Villages in Maremma

The city of Grosetto lies on the southern corner of Tuscany in the region of Maremma. The colourful palette of its natural wonders includes lovely beaches, soft hills and natural thermal pools.

Lovely hilltop village of Massa Maritima with the surrounding fields
Lovely hilltop village of Massa Maritima with the surrounding fields- Credit:

Massa Marittima

This hiltop town surrounded by green fields lies 20 km from the coast. The highlight of the visit is the Cathedral of San Cerbone at the centre of Piazza Garibaldi.

Mining has been a hidden treasure of Massa Marittima and a source of living. The Mining Museum shows the vast panorama of minerals in the past.

The history of the town belongs to the Etruscans.

Chandelier Tower from the 13h century offers fascinating panoramic views of the surrounding hills.

Conclusion- The Incredible Charm of the Tuscanian Villages

Tuscany is the treasure that belongs to a dream, its villages shine with the living poetry inspired by the medieval Europe. The artistic heritage belongs to paintings and returns the splendid views of paintings.

The hilly towns are abundant in images of nature with the typical cypresses, soft hills and medieval spirit. Magic just needs to exist here along the protected valleys of UNESCO.

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