Home | About Self-Guided Travel | Italy | Spain | England | Reserve an Adventure | About Zephyr

Terra di Siena Bike Dream - Biking - Itinerary

View Overview Reserve This Adventure Map This Adventure Reservation Policy

Day 1: BENVENUTI! Arrival in Arezzo

The Zephyr Guide will meet you in Arezzo, provide you with maps and route directions, make sure your bike is properly fitted, and answer any questions you might have.

The Day's Highlight: You can arrive any time you wish and so there is no riding today. However, enjoy a walk through Arezzo's streets.

Ride Details: No riding.

About the Town: Arezzo has been an important town since Etruscan times and its central piazza and magnificent gothic Duomo are highlights for any visitor.

Day 2: Ride from Arezzo to Cortona

The Day's Highlight: Beautiful views of the valley along the way and a stop in the medieval town of Castiglion Fiorentino.

Ride Details: Basic Route: EASY- 49 km (20% gravel, 80% asphalt) mainly flat route with some short and easy hills. An option long route of 70 km. A very nice and easy ride, mostly flat along the Val di Chiana flatlands.

About the Town: Cortona is an ancient Etruscan hilltown close to the border with Umbria. The city boasts an historic piazza with Etruscan walls and Renaissance churches and was described in the book "Under the Tuscan Sun."

Special Event of the Day: Walk along the ancient city walls of Cortona, imagining the history as you see the 5th Century BC base created by the Etruscans.


The Day's Highlight: Seeing the town of Montepulciano in the distance as you approach the hilltop town.

Ride Details: MODERATE - 45 km (100% asphalt) through rolling hills with a big final climb to Montepulciano at the end. A longer route of 70 km is available.

About the Town: Montepulciano is a medieval walled town built on a limestone ridge, with many beautiful Renaissance style palazzi and churches. The town is very pedestrian-friendly and a great place to walk.

Special Event of the Day: Taste the famous Vino Nobile wine from a streetside cafe in the middle of town.


The Day's Highlight: This is a fantastic loop route through the heart of Central Tuscany. Pienza, the dream town of Pope Pius II, is a place of architectural masterpieces, beautiful ceramics, and delectable pecorino (sheep's) cheese. The long route extension includes a stop in Bagno Vignoni, famous for its thermal springs!

Ride Details: MODERATE - km 45 (25% gravel 75% asphalt) on rolling hills with a longer route (65 km) available. The ride up to Pienza is a tough climb but well worth it!

Special Event of the Day: Shop for lunch in a market in Pienza and eat while overlooking the valley on top of the city walls.


The Day's Highlight: Visit the church of S. Anna with a fresco by Sodoma after enjoying your ride along the most beautiful "Strada Bianca" of Tuscany.

Ride Details: MODERATE - 50 km (70% dirt 30% asphalt) on rolling hills with a long climb to Montalcino at the end. A longer route of 75 km is available.

About The Town: Montalcino is a medieval hilltop town famous for its imposing "Fortezza" (fortress), the delicious Brunello red wine, and honey.

Special Event of the Day: Buy a bottle of Brunello in Montalcino and sip it in the Fortezza, with sunset views of the surrounding area.


The Day's Highlight: Views of Tuscan towns and countryside abound as you ride to the imposing Abbey of Monte Oliveto Maggiore, which dominates the Crete Senesi (Siena Clays). This is a wonderful ride across gorgeous rollercoaster roads.

Ride Details: MODERATE - 65 km (100% asphalt) on rolling hills with a longer route of 75 km available.

About the Town: Monte San Savino was another Etruscan town that was fortified by the Romans and is a great place for an overnight stay.

Special Event of the Day: See the frescoes by Sodoma on the main cloister in the Abbey of Monte Oliveto Maggiore.


The Day's Highlight: A relaxing easy loop ride across the fields of the Chiana Canal, bursting with sunflower, apple, and corn, and back to Monte San Savino.

Ride Details: EASY - 30 km (95% asphalt) route that loops back to the hotel. An extension adds 11 km (60% asphalt). After showering, we will shuttle you back to your starting point in Arezzo.

Contact Us | Press & Travel Agents | Affiliates | Partners | Privacy Policy