The best traffic-free bike rides around Castiglion Fiorentino

Montecchio Vesponi Castle dominates the Val di Chio from a hill over 360 meters above sea level. With its crenellated walls, towers, and an imposing 30-meter-high square tower, it is one of the best-preserved medieval castles in Tuscany and can be recognized from afar throughout the valley. Contested for centuries by Arezzo and Florence for its strategic position on the road to Cortona, it became a Florentine stronghold after the Battle of Campaldino in 1289. In the 14th century, it was also home to the famous mercenary captain John Hawkwood. Today, the castle comes back to life with guided tours, events, and reenactments that evoke the atmosphere of the Middle Ages.

In Castiglion Fiorentino, just outside the city walls, stands the Church of the Madonna della Consolazione. Its history stems from a sacred image of the Madonna and Child, attributed to Luca Signorelli, once kept in a tabernacle along the road. Tradition holds that Eleonora di Toledo, wife of Cosimo I de' Medici, regained her sight by praying before that image. In gratitude, she financed the construction of the church, which began in 1565 and was completed only decades later. Inside, in a side chapel, the original fresco of the Madonna is still preserved.

Dominated by the imposing Torre del Cassero, this medieval village offers one of the most spectacular views of the Valdichiana and the Val di Chio below. A stop in the Piazza del Municipio allows you to admire the elegant Vasari Loggias, a true natural terrace that frames the Tuscan landscape in a timeless atmosphere.

Muzzicone is famous for Florentino grilled steaks.. Best around!

A few kilometers of well-maintained gravel road

Obelisk to Giuseppe Garibaldi, Castiglion Fiorentino The monument to the fallen in Piazza Giuseppe Garibaldi: a symbol of all the Risorgimenti.

Chiesa di San Francesco, Via Alessandro Codivilla, Castiglion Fiorentino The church, overlooking the square of the same name, was built by the Franciscans in the mid-13th century on an existing 12th-century structure, first dedicated to San Salvatore and then to San Leonardo. The building has a Romanesque-Gothic sandstone façade featuring a slender mullioned window surmounted by a small rose window. On the lunette of the portal, one can admire a terracotta depicting Saint Francis teaching the turtledoves how to breed, a work by Antonio Brogi, a local ceramist from the year 900. The interior, according to Franciscan custom, consists of a single nave, closed off by a short transept with three cross-vaulted chapels. The roof is gabled. Altars from the 16th and 17th centuries lean against the walls, and one can admire works by Francesco Morandini known as "il Poppi" (Crucifixion), Giorgio Vasari (Madonna with Saints Anne, Sylvester, and Anthony), and Salvi Castellucci (Invocation of Saint Matthew and Annunciation to Saint Anne). Note the third niche on the right, now empty, which once housed a Saint Francis by Margarito d'Arezzo. Below, protected by a grille, was the Holy Cross, a 13th-century reliquary of exceptional value. Both works are now on display in the Pinacoteca di Santa Maria Novella. Also of great importance are the wooden crucifix, painted in faux bronze by Giovanni Patriarca, and a wooden statue of Christ Captured in the Garden of Olives, created in 1651 by Sallustio Lambardi of Lucignano, which is carried in procession by the Society of Saint Anthony on Holy Tuesday. The choir, in Pietra Serena, whose decoration consists of panels, dates from 1546. The two central panels depict Saint Michael and Saint Francis, with floral motifs on the sides. The whole is supported by two large double-voluted shelves and plant motifs. On the left side of the church is a rectangular cloister, rebuilt in the early decades of the 17th century on a 13th-century portico, and characterized by a double loggia in the Tuscan style, with a circular fountain at its center. Under the arches of the lower tier, you can admire the frescoed lunettes depicting scenes from the life of Saint Francis, a seventeenth-century work by Pelliccione da Colle. Inside the cloister, you can see the tombstones of many important figures from Castiglione who wished to be remembered here. On the right side of the church, the oratory of the Company of Saint Joseph was built in 1560; in 1785, the company was dissolved and the oratory was sold to private individuals. Text / Source: Turismo Comune Castiglionfiorentino https://turismo.comune.castiglionfiorentino.ar.it/contenuti/242169/chiesa-san-francesco

Le Logge Café, Town Hall Square, Castiglion Fiorentino Le Logge Café, Town Hall Square, 4/5, 52043 Castiglion Fiorentino AR, Italy Tel. 0039 347 831 96 43