The itinerary will guide you through the historical and artistic treasures of the city, among palaces, churches, monuments, and scenic viewpoints.

We begin our fascinating tour at the evocative Porta Bifora, one of the main gates welcoming visitors into the heart of the city. From this point, we’ll delve into the picturesque streets of Via Guelfa, passing through the ancient Porta San Vincenzo, to reach the true beating heart of the city: Piazza della Repubblica.

This square represents a historical crossroads, where the two main roads of Roman Cortona—the Cardo and the Decumanus—intersected, forming the North-South and East-West axes. It is right here that the forum came to life, the focal point of the city, a place steeped in history and culture. Through our tour, we’ll explore together the roots and the stories hidden behind every corner of this captivating square.

Overlooking Piazza della Repubblica stand important historic buildings, including the Palazzo Comunale, which dates back to the 12th century, and the Palazzo del Capitano del Popolo, later transformed in the 16th century into Palazzo Passerini. The imposing arches of the Logge della Pescheria frame the square, offering enchanting views of small piazzas and Renaissance buildings.

Our path will then lead us to the evocative Piazza Signorelli, where the austere and prestigious Palazzo Casali takes center stage—now home to the Museum of the Etruscan Academy and the City of Cortona, known as MAEC. As we continue together, we’ll explore the historical and artistic treasures that define this place, immersing ourselves in the echoes of the past.

The palace has 13th-century origins and was once the residence of the powerful Casali family, rulers of the city from 1325 to 1409. The Signorelli Theatre, located in the square of the same name, is also part of the visit, with the possibility to explore its interior.

Heading down Via Casali, we’ll reach Piazza del Duomo, home to the Cathedral dedicated to Santa Maria Assunta, built in the 16th century. Originally, it was the Parish Church of Santa Maria, documented as early as the 11th century and constructed over the remains of an ancient pagan temple. Inside, it preserves important works of art, including the Adoration of the Magi by Pietro Berrettini.

In front, we’ll find another important place of worship: the Church of the Gesù, with its prestigious oratory. Today, the church houses the Diocesan Museum of the City of Cortona, established in 1945. Among its treasures is the refined Annunciation by Beato Angelico, as well as works by the master Luca Signorelli, including the Lamentation over the Dead Christ, painted in 1502 for the high altar of the Church of Santa Margherita—an artwork of great sculptural power and vivid color.

Also notable is the splendid Assumption of the Virgin Giving the Girdle to St. Thomas, a masterpiece by Bartolomeo della Gatta, dated to the early 1470s. From the square, one can also admire a stunning pre-Apennine panorama, with the prominent peak of Monte Sant’Egidio (1,057 m).

The tour continues along Via Jannelli, with an external visit to the picturesque Medieval Houses. From here, we’ll return to Piazza della Repubblica, heading up Via Roma, where you can admire the rear side of the Town Hall and its tower.

Climbing Via Benedetti and Via Maffei, we arrive in front of the monumental Church of San Francesco, built on a large artificial terrace, probably of Roman origin, once the site of thermal baths known as the “Queen’s Baths” (Bagni della Regina). The church was designed between 1245 and 1246 by Friar Elia Coppi, the first Minister General of the Order of Friars Minor.

The original conventual architecture—sober and austere—was altered starting at the end of the 16th century, when the frescoes decorating the walls were whitewashed and side altars in pietra serena were installed.

The Church of San Francesco is the first and most significant example of a typology that became the most widespread within Franciscan architecture. The church rises majestically above the staircase, which was rebuilt in the first half of the 17th century. Inside, it houses distinguished relics: the funeral pillow of Saint Francis, the reliquary of the Holy Cross, and a tunic traditionally believed to have belonged to Saint Francis.

Returning to Piazza della Repubblica, and descending along Via Cantucci, we’ll stroll down the city’s main street, Via Nazionale, affectionately known by the locals as “Rugapiana”.

We will slowly walk by ancient palaces dating from Renaissance and seventeenth-century periods. We will also walk by the many local shops and typical restaurants of the area. Then finally we will reach the third and last square, Piazza Garibaldi.

Here, you’ll be enchanted by the beautiful view of the Valdichiana Valley, as well as by the nearby Church of San Domenico. The current complex dates back to the late 15th century.

It was in this very Dominican building that, in 1438, Beato Angelico created one of his finest Annunciations for one of the church’s altars, a masterpiece now preserved inside theDiocesan Museum.

Adjacent to the Church of San Domenico, you’ll find the Public Gardens, the “Parter”, where you can glimpse a charming corner, surrounded by ancient convents and monasteries with their sail bell towers. The park features an avenue of about 3 km.

Additionally, from this side (to the left of the entrance to the Parterre), you can admire part of the splendid Mosaic by Gino Severini, depicting Saint Mark, the patron saint of Cortona.

The afternoon can be dedicated to a visit to the upper part of the city, with the Sanctuary of Santa Margherita, the Patroness of the City and a Franciscan tertiary. Upon her death (February 22, 1297), it was decided to build a church in her honor, beside the ancient church of San Basilio, which Margherita herself had restored after choosing it as a place of penance.

The church was designed by Giovanni Pisano and frescoed internally by Pietro Lorenzetti. Unfortunately, little of the original building remains today. The current church is the result of 19th-century reconstruction. Dominating the hill of Cortona is the Girifalco Fortress, which is also open to visitors, where you can stop for a snack and taste local products inside the Bistrot.

Cortona also offers other places to visit, truly rich in spirituality and breathtaking scenic views, such as the Eremo delle Celle, located at the foot of Monte Sant’Egidio, a place where nature and silence reign supreme. The hermitage was founded in 1211 by Saint Francis with his first Cortonese brothers, the blessed Guido Vagnotelli and Friar Elia.