Choosing between so much brilliant architecture, first-class art, sublime landscapes and good food is an almost impossible task when looking at the  towns of Tuscany.  

Around the magnificent Florence and Siena a lot of populations swirl that reproduce on a small scale the milestones of the great capitals of the Middle Ages and the Renaissance. Places where it is very easy to sound; where well understood romanticism flows through the pores of those who visit it and where it is not surprising that dozens of artists settled in search of inspiration and inner peace. Its famous landscapes full of vineyards and multicolored sunsets between the green of the plains, the brown of the rocks, the reddish of the sunset and the crimson of the roofs, fill the imagination of anyone who thinks of Italy and Tuscany.

Montefioralle

In the Chianti valley, famous above all for its wines, stands out this small and charming medieval town with cobbled streets and flowers on the windowsills. Every September the Expo del Chianti Clasico festival is held here, which allows you to taste the region’s wines and learn more about their excellence.

Montalcino

From afar you can see the portentous fortification, perched on a hill, of Montalcino. In this town some of the best wines in Italy are produced, the Brunello, as well as the Rosso di Montalcino i Sant’Antimo The town is located between Mount Amiata and the sea, about 45 kilometers from Siena, in the heart of the Orcia Valley and its origin dates back to the twelfth century. The walk through its cobbled streets has many attractions, and one of them, without a doubt, is to sit in one of its small squares to taste a glass of red wine. 

Certaldo

The hill on which this little town lies is so narrow and variegated that Certaldo is one of the few monumental towns in Tuscany that does not have a square. To compensate, this settlement, inhabited since Etruscan times, has a street, Via Bocaccio, which not only reminds us that one of the great writers of the Italian language was born here. It also houses the cathedral, the remains of the loggia (now walled) and the main palazzi, among which the Stiozzi Ridolfi stands out. Of course, here all the tourist signs lead to its great monument, the Praetorian Palace, the mother house of the Counts Alberti, where the audience room, the jails, the chapel and the private rooms of the Vicars shine with their own light.

Also close to Siena is the best-preserved medieval citadel in the region, which stands on a hill, 324 meters above sea level, dominating the Elsa Valley. With its fourteen square towers rising on the horizon (it originally had 71), the city is full of must-see monuments such as the Collegiata, the 12th-century cathedral with Renaissance frescoes, the 13th-century Palazzo del Popolo and the Church of San Agostino, another Tuscan Romanesque jewel.

Saint Gimignano

Also close to Siena is the best-preserved medieval citadel in the region, which stands on a hill, 324 meters above sea level, dominating the Elsa Valley. With its fourteen square towers rising on the horizon (it originally had 71), the city is full of must-see monuments such as the Collegiata, the 12th-century cathedral with Renaissance frescoes, the 13th-century Palazzo del Popolo and the Church of San Agostino, another Tuscan Romanesque jewel.

Montepulciano

South of Siena is this town of delicious wines, such as the Vino Nobile of Montepulciano, and exceptional architecture. The Piazza Grande is its center and accumulates a good handful of buildings such as the Town Hall, Gothic and with a high tower from which you can see everything around. The Cathedral and the church of San Agostino, along with the sanctuary of the Madonna del Biagio, on the outskirts, are must-sees.

Pienza

All the essence of Tuscany is concentrated in this town and its surroundings with slight hills on which rows of cypresses zigzag. Pienza arose from the dream of Pope Piccolomini who in the fifteenth century undertook the task of turning a small village into a model Renaissance city. All the streets lead to the main square where the wonderful Duomo emerges and in whose surroundings you can buy and taste the pecorino cheese. Do not miss the view from the viewpoint with a spectacular panoramic view of the Valle di Orcia .

Volterra

A few kilometers from San Gimignano is Volterra, a splendid compendium of architecture and art from different Etruscan, Roman, Medieval and Renaissance periods. The Roman theater and the solid walls that surround a beautiful medieval quarter are some of its attractions.

Monteriggioni

Between Siena and Florence is this small walled town with high medieval towers where time seems to have stopped. The castle was founded in the middle of the 13th century by the Republic of Siena to defend itself against the Florentines, until in the 16th century, both were annexed to Florence. With several entrance doors to the city, it is convenient to take a walk along the walls to get an exact idea of ​​what the town and its surroundings are like.

Cortona

It is one of the oldest Etruscan settlements in Tuscany, founded in the 5th century BC Located in the south of the region, Cortona became a center of traveling pilgrimage a few years ago when the book and the film Under the Tuscan Sun were released . highlight its undoubted charm. The views of the entire Val di Chiana from the top of the town are impressive.

Pistoia

Off the beaten tourist track and halfway between Florence and Lucca, Pistoia looms , with its ocher-tiled roofs announcing a model Tuscan town. This city is claimed as an excellent stopover to get to know the authentic Tuscany, whose roots go back to the Middle Ages. In Piazza del Duomo we find the set of buildings that are essential to visit: the cathedral, the baptistery and the campanile. For art lovers, the Museo Civico and the Museo Marino Marini exhibit Pistoian art and history. And for the most folklore, the Giostra dell’Orso,a journey through time that, every year at the end of July, transforms Pistoia into a medieval setting.

Anghiari

In the province of Arezzo , this small town of stacked houses stands out on an ancient Roman site. The monastery of San Bartoleo and the church of the Badi a are its two most representative medieval monuments, but there is much more, palaces, small oratories, patios that house pleasant restaurants  that can be discovered on a walk through its steep and narrow streets.

Pitigliano

A set of winding, cobbled alleys, elegant arches and picturesque rock houses make up this town of Etruscan origin that became a fiefdom of the wealthy Aldobrandeschi and Orsin families. They expanded the fortress, reinforced the walls and built the imposing aqueduct. Piazza Petruccioli and Piazza Garibaldi remain from that time , connected to each other. An essential visit in Pitigliano is the Piccola Gerusalemme, the former ghetto where the Jewish community settled when Pope Pius IV expelled them from Rome in the 16th century.

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