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Easy to reach and always a delight to see, Tuscany is a well-known destination that never fails to amaze, no matter the season. For the Immaculate Conception long weekend or New Year’s Eve, for example, we invite you to join us on an organized tour led by a local nature guide to discover the still-little-known village of Castiglion Fiorentino, where you can lose yourself in its narrow streets and fragrant scents. You’ll also discover Arezzo, a city on a human scale that, between November and January, comes alive with the events and magical atmosphere of the famous “City of Christmas” in its streets and palaces. Your passion for easy hikes will be satisfied with a day’s walk along the Via Romea Germanica, one of the most important pilgrimage routes connecting Germany with Rome, which, in this area, intersects with the Via Clanis. Are you ready to follow in the footsteps of one of Italy’s most beautiful trails? The gentle slopesof the Tuscan Apennines and the picturesque villages of the Valdichiana will captivate you, offering you a weekend or New Year’s Eve getaway in a city unlike any other. Come hike with us!
WHERE ARE WE GOING?
Program
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 the narrow streets typical of a medieval village with Etruscan influences, surrounded by historic walls, tower houses, abbeys, and the Logge del Vasari. In the evening, we’ll meet 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
After a hearty breakfast at the B&B, we’re ready for this first day of group hiking. The town of Castiglion Fiorentino is one of the most beautiful and important in the Arezzo Valdichiana and occupies a privileged location, serving as a link between the Clanis Valley and the Valdichio—a natural amphitheater nestled among green ridges. The Via Clanis, spanning 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 surrounded by Mediterranean scrub.
Third day
Arezzo: Art and Hills
During our regular weekends: today we’ll explore Arezzo. On a guided urban hike, we’ll stroll through its ancient streets before venturing into the nearby countryside and the hills surrounding the city. Carducci once 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 and well-known Renaissance painting cycles in the world: Piero della Francesca’s “Legend of the True Cross.” In the afternoon, we’ll return to Castiglion Fiorentino for dinner together.
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 Castle of Montecchio Vesponi, a picturesque manor 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 town of Cortona, a charming historic town in the Valdichiana, surrounded by ancient Etruscan walls. It sits on a hill at an elevation 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 made of pietra serena 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 is over, we’ll say goodbye to this corner of Tuscany and can depart directly from here.
Overnight stay in double rooms at a B&B; twin beds are available only on New Year's Eve
breakfasts and 3 dinners in a restaurant
Full-day expert environmental guide and guided tours
health and baggage insurancetravel, meals and beverages, train ticket to Arezzo, tourist tax, and anything not listed under “Includes.”
Single occupancy starting at €50, depending on the season.
B&B in Castiglion Fiorentino - AR. Located in an ancient medieval village in the heart of Tuscany, this B&B is designed to help you slow down and indulge in life’s little pleasures. It offers an intimate atmosphere, tastefully decorated rooms, and a sense of tranquility that invites you to step away from the daily grind. A place where you can rediscover the joy of taking time for yourself, surrounded by history and the rolling Tuscan hills.
For New Year’s Eve, the group may be accommodated in several B&Bs located in the center of Castiglion Fiorentino or in neighboring areas.
Train to Castiglion Fiorentino; from the station to the B&B it is about a 15-minute walk. Alternatively, contact the B&B for a free ride (just let them know at least 20 minutes before arrival) or check the availability of taxis on site (the cost is around €10). The B&B rooms are available from early afternoon, and the meeting with the guide will be around 7-7:30 p.m. On the last day, the tour ends around 3 p.m., and we recommend taking the train from Camucia-Cortona station. If you arrive by public transport, you will use the cars of the other participants, paying a reimbursement to those who make their cars available.
On New Year's Eve, we recommend arriving by car because we will need them to reach Arezzo on the evening of December 31! If you arrive by public transport, you will use the cars of other participants, paying a reimbursement to those who make their cars available.
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