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Through villages and hills: Arezzo, Cortona, and Valdichiana

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Trekking with a local guide to discover some Tuscan villages such as Cortona, Castiglion Fiorentino, and the city of Arezzo. Choose between the long weekend of April 25 or the end of May.

Spring is the perfect time for an easy weekend hike through hills, olive groves, and Tuscan villages. With a local nature guide , you’ll walk along a section of the Via Romea Germanica, where it meets the Via Clanis, and you’ll have time to explore the narrow streets of Cortona, Arezzo, and the more intimate Castiglion Fiorentino: historic streets, gentle views, and a few tasty stops. The pace is relaxed, no pressure to perform, and we handle all the logistics. Why choose this tour? You’ll enjoy easy hikes of 10–12 km, local storytelling, and authentic tips for making the most of your weekend. I recommend this itinerary to friends, solo travelers, or couples who prefer small groups and flexible schedules. Arezzo, Cortona and the Valdichiana, a mini-vacation of 4 days.


Travel code
ARETK
When are we leaving?
Based on the date
When are you coming back?
Based on the date
How long does it last?
4 days 3 nights
Per person
490 €

WHERE ARE WE GOING?

Program

First day

Welcome to Valdichiana
Free arrival in Castiglion Fiorentino, a Tuscan village nestled in the heart of the wonderful Valdichiana. Leave your car at home: reach Castiglion Fiorentino by train, from the station to the B&B it is about a 15-minute walk, or you can always ask for a ride to the property. Leave your luggage in your room and start walking through the typical alleys of a medieval village with Etruscan influences among historic walls, tower houses, abbeys, and Vasari's Loggias. In the evening, we will meet with our local guide , who will tell us about the weekend ahead, and we will enjoy our first typical dinner together in a restaurant.

Second day

On the trails of Via Clanis
A hearty breakfast at the B&B and we're ready for our first day of group trekking. The village of Castiglion Fiorentino is one of the most beautiful and important in the Valdichiana and enjoys a privileged position linking the Clanis Valley and the Valdichio, a natural amphitheater enclosed by green ridges. The Via Clanis , with its 8 stages, forms a circuit of the Valdichiana between the provinces of Arezzo and Siena. We will walk along these paths discovering its ancient history, enjoying unexpected views, crossing geological features and even encountering a canyon and Mediterranean scrub all around.

Route info: 13 km, elevation gain of approximately 500 meters

Third day

Arezzo between art and hills
Today we will discover Arezzo. With a guided urban trek , we will walk through its ancient streets and then venture into the nearby countryside and hills surrounding the city. Carducci said: "Arezzo alone would suffice for the glory of Italy." At times, it will feel like we are walking in another era, in the time of Piero della Francesca, and in this regard, we will visit Bacci Chapel inside the Basilica of San Francesco in Arezzo, decorated with his frescoes. Here we will admire one of the most famous and known throughout the world, the "Legend of the True Cross" by Piero della Francesca. In the afternoon, we will return to Castiglion Fiorentino for dinner together.

Route info: 13 km, elevation gain of approximately 450 meters (on New Year's Eve, the hike will be a little shorter)

Fourth day

Cortona from above
Today we visit the beautiful Cortona, a charming historic town in the Valdichiana, surrounded by ancient Etruscan walls. It stands on a hill about 600 meters above sea level, offering a splendid view of the Valdichiana and Lake Trasimeno in Umbria. Its iconic symbol is the Palazzo Comunale, with its characteristic clock tower, the striking sandstone staircase overlooking Piazza della Repubblica, the beating heart of the city, and finally the famous Franciscan hermitage, the "Celle" di Cortona. After the guided trek , we say goodbye to this corner of Tuscany and can leave directly from here.

Route info: 10 km, elevation gain of approximately 300 meters
  • overnight stay in double rooms in B&Bs
  • breakfasts and 3 dinners in a restaurant
  • Full-day expert environmental guide and guided tours
  • health and baggage insurance
travel, meals and drinks, train ticket to Arezzo (if applicable), tourist tax, and anything not mentioned under "Includes."
Single occupancy accommodation from €50.
Good to know
Where
accommodation
B&B in Castiglion Fiorentino - AR. Located in an ancient medieval village in the heart of Tuscany, this B&B is designed to slow down and indulge in small pleasures. An intimate atmosphere, well-kept rooms, and a sense of tranquility that invites you to disconnect from the daily grind. A place where you can rediscover the joy of time for yourself, surrounded by history and the rolling hills of Tuscany.
Tour guide
A member of the Jonas team who coordinates the group and accompanies them throughout the trip.
Itinerary information
Travel times are approximate as they vary from group to group. Daily excursions usually last around 4-5 hours, with an elevation gain of around 300-500 meters.
Notes
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. Photo credits: www.arezzomedia.com
Important
The program may be subject to change due to weather conditions, traffic conditions, closing times, and/or at the discretion of the tour guide.
Train

Train to Castiglion Fiorentino; from the station to the B&B it is about a 15-minute walk, alternatively contact the property 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 can use the cars of the other participants, paying a reimbursement to those who make their cars available.

Cars

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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