A Weekend and New Year's Eve in Tuscany Between Cortona and Arezzo

First day

Welcome to Valdichiana
Arrive at your convenience in Castiglion Fiorentino, a Tuscan village nestled in the heart of the beautiful Valdichiana. Leave your car at home: reach Castiglion Fiorentino by train; it’s about a 15-minute walk from the station to the B&B, or you can always ask the B&B for a ride. Drop off your luggage in your room and start strolling through these narrow streets typical of a medieval village with Etruscan influences, among historic walls, tower houses, abbeys, and the Logge del Vasari. In the evening, we’ll meet up with our local guide , who will give us a preview of the weekend ahead, and we’ll enjoy our first traditional dinner together at a restaurant.

Second day

On the Trails of the Via Clanis
A hearty breakfast at the B&B, and we’re ready for this first day of group hike. The town of Castiglion Fiorentino is one of the most beautiful and important in the Valdichiana in the Arezzo area and enjoys a privileged location where the Clanis Valley meets the Valdichio—a natural amphitheater nestled among green ridges. The Via Clanis , with its 8 stages, forms a circuit around the Valdichiana between the provinces of Arezzo and Siena. We’ll walk along these trails, discovering its ancient history, enjoying unexpected views, passing through unique geological features, and even encountering a canyon and the surrounding Mediterranean scrub.

Third day

Arezzo: Art and Hills
On a typical weekend: Today we’ll explore Arezzo. With a guided urban hike , we’ll wander through its ancient streets before venturing into the nearby countryside and the hills surrounding the city. Carducci said, “Arezzo alone would be enough for Italy’s glory.” At times, it will feel as though we’re walking through another era—the time of Piero della Francesca—and in that spirit, we’ll visit the Bacci Chapel inside the Basilica of San Francesco in Arezzo, which is adorned with his frescoes. Here we’ll admire one of the most famous Renaissance painting cycles and best-known in the world, the "Legend of the True Cross" by Piero della Francesca. In the afternoon, we’ll return to Castiglion Fiorentino for dinner together.
For New Year’s Eve only: On the morning of December 31, we’ll go on a light hike along the Via Romea Germanica , which will take us to the Montecchio Vesponi Castle, a picturesque castle dating back to the year 1000. In the late afternoon, we’ll head to Arezzo (in participants’ cars) to tour the city and celebrate New Year’s Eve in the square. Dinner at a traditional restaurant.

Fourth day

Cortona from Above
Today we’re visiting the beautiful Cortona, a charming historic town in the Valdichiana, surrounded by ancient Etruscan walls. It stands on a hill at an altitude of about 600 meters, offering a splendid view of the Valdichiana and Lake Trasimeno in Umbria. Its iconic symbol is the Town Hall, with its distinctive clock tower, the striking staircase of “pietra serena” stone that dominates Piazza della Repubblica—the beating heart of the city—and, last but not least, the famous Franciscan hermitage, the "Celle" of Cortona. Once the guided hike , we’ll bid farewell to this corner of Tuscany and can set off again directly from here.