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The most beautiful towns of Tuscany and Umbria

The area of Cortona and its surroundings is rich in history and traditions. As a cradle of Italian art and culture, this region, straddling Tuscany and Umbria, is the green heart of Italy.

Paesaggio Cortona di notte Toscana
Cortona

Lying like an ancient slumbering entity on the hill north of Lake Trasimeno, Cortona retains the intense stratifications of history from the Etruscan to the Renaissance era. The city uniquely merges urban quality and monumental spaces, rich in art and history, with glimpses of rural life, where monastery gates, little churches nestled in greenery, and houses climbing steeply up to the Poggio, convey the flavor of sleepy, secluded rural villages in the quiet Tuscan countryside.
Its formidable Etruscan walls, smoothed by centuries and winds, enclose a wealth of art and culture, from the Etruscans to Beato Angelico, Luca Signorelli, and Pietro Berrettini, all to leave us breathless and amazed by such beauty.

3,5
Km
Piazza Grande Arezzo Toscana
Arezzo

In the heart of the medieval city, everything speaks of the great eras of Arezzo's architecture and art. This is an itinerary through the memory of the proud commune, narrated by the ancient faces of houses and streets, the color of the sandstone, the unique and beautiful Piazza Grande, and the churches and public buildings that survived the Florentine destructions. Not to be missed are the Saracino Joust, a grand historical reenactment and district competition, the antiques fair, "The Legend of the True Cross" by Piero della Francesca, Cimabue's crucifix, and many examples of Arezzo's renowned gold and silver craftsmanship.

25
km
Veduta Montepulciano Toscana
Montepulciano and Pienza

A day discovering two delightful towns: Montepulciano, said to have been founded by the Etruscan Porsenna and certainly existing since 714 B c. The town, adorned with numerous Renaissance artists' works, is known as the "Pearl of the 16th Century," and today, along with its famous Vino Nobile, is renowned worldwide. Stopping to admire the church of San Biagio and the surrounding panorama, we move on to Pienza, also a true gem commissioned by Pope Pius II, representing the first application of humanistic-Renaissance urban planning concepts and the nucleus for the development of the ideal city project.

30
km
Paesaggio Val d'Orcia Toscana
Val d’Orcia

Gentle rolling hills alternate with sudden cliffs and gullies, creating a varied and picturesque landscape. Val d'Orcia boasts natural and artistic treasures of great value. Mount Amiata overlooks this valley, feeding it with its warm waters springing from the underground, making Bagno Vignoni and Bagni San Filippo important thermal centers.

30
km
Veduta Valtiberina Toscana
Valtiberina

Follow in the footsteps of Piero della Francesca. Castles, parish churches, abbeys, ridge villages rich in history, and two small but precious art cities, Anghiari and Sansepolcro, form the heart of this beautiful area. Not to forget, Monterchi, which houses another great work of the illustrious painter: La Madonna del Parto.

40
km
Piazza IV novembre Perugia
Perugia and Torgiano (Deruta)

Perugia, the capital of Umbria, is an ancient and majestic city. . Its unique cloverleaf shape encloses the high city on the hill, the former Etruscan and Roman acropolis, from which medieval boroughs stretch down the ridges. The historic center is rich in masterpieces harmoniously integrated into the urban fabric built over millennia of history. Numerous exhibitions and events include Eurochocolate and Umbra Jazz. Nearby Torgiano, an ancient medieval village, is renowned for its wine and oil museum.

55
km
Veduta Montalcino Toscana
Montalcino and the Abbey of Monte Oliveto Maggiore

When thinking of Montalcino, Brunello wine immediately comes to mind. However, Montalcino is not just about wine; it's also a fortified city preserving part of its 19 towers and ancient sources, lending it a severe and charming aspect. The beautiful medieval buildings are enlivened by typical shops and wine bars. The rugged part of the Crete Senesi features the unmistakable Abbey of Monte Oliveto, a splendid monastery defended on three sides by sheer cliffs and surrounded by a large park enhanced by a 16th-century fishpond.

60
km
Piazza del Campo Siena Toscana
Siena

A magical atmosphere pervades the streets and squares of Siena, hiding unexplored and incomprehensible secrets within its stern grandeur. This is Siena, the mysterious, breathtakingly beautiful with its intertwining streets and alleys. Protected by its ancient gates, it encloses a true gem of beauty: Piazza del Campo, overseen by the tall and majestic Torre del Mangia.

60
km
Basilica San Francesco Assisi Toscana
Assisi and Spello

At the heart of Christian spirituality, Assisi unfolds on terraces along the slopes of Mount Subasio, with a clearly medieval structure superimposed on the Roman town. The historic center, centered around the Franciscan Basilica and the three main squares of the Commune, San Rufino, and Santa Chiara, contains exceptional monuments of architecture and figurative art. In the same day, a visit to Spello, a characteristic town at the foot of Mount Subasio, is recommended; the Church of Santa Maria Maggiore alone, with works by Perugino and the beautiful Baglioni Chapel frescoed by Pinturicchio, is worth a visit.

70
km
Borgo San Gimignano Toscana
San Gimignano

Not far from Siena is San Gimignano, the city of tower houses, of which thirteen remain intact, with remnants of many more. At its zenith, seventy-two towers were raised. . In its delightful square or under the shadow of a tower, one can savor a glass of Vernaccia, the typical white wine of San Gimignano.

80
km
Palazzo dei Consoli Gubbio Toscana
Gubbio

Founded by the Umbrians, who made it their capital. The houses in Gubbio seem sculpted in limestone, displaying a chromatic uniformity that expresses the city's strength. Its attachment to ancient traditions, like the Corsa dei Ceri, complements the vitality of age-old artisanal activities such as ceramics, wrought iron, lutherie, and the restoration of antique furniture. Not to be missed are the Palazzo dei Consoli and the Ducal Palace, the Renaissance residence of Federico da Montefeltro.

80
km