Cortona to Siena Cycling Tour

Welcome to the stunning hill town of Cortona, perched above the Chiana River Valley. Famous for its delicious Chianina steak, this medieval town dates back to 600 BC, offering a perfect introduction to Tuscany. Take time to explore the Etruscan Museum or admire Fra Angelico’s paintings at the Diocesan Museum. This afternoon, we'll gather for a bike fitting and briefing to get you ready for your Tuscan adventure!

Pedal your way to the picturesque shores of Lake Trasimeno, where Hannibal famously defeated the Romans after crossing the Alps with elephants! If you’ve got extra time, take a boat ride to Isola Maggiore for stunning views. On your way back to Cortona, cycle through the rolling hills that inspired Frances Mayes in Under the Tuscan Sun. For a more relaxed ride, opt for the scenic route to Castiglione del Lago, a charming village perched on a cliff, and enjoy a leisurely afternoon back in Cortona.

Easier option to Castiglione: daily distance 64 km (40 miles); elevation gain + 715 m (2345 ft)

Harder option to Lake Trasimeno: daily distance 53 km (33 miles); elevation gain +1022 m (3352 ft)

Today, ride to Montepulciano, renowned for its famous Vino Nobile di Montepulciano. Wander through the medieval streets and stop by one of the local wine cellars for a tasting. After enjoying lunch, head towards Pienza, one of the first planned Renaissance towns. With the help of architects during the 16th century, Pope Pius II transformed his humble hometown into a breathtaking masterpiece.

Today’s loop ride takes you deep into the Orcia Valley, a stunning landscape known for its vibrant hills that change color with the seasons. Cycle through the tiny medieval village of Monticchiello and experience the valley's unique charm. As you return to Pienza, take time to sample the local wines and cheeses, including the famous Pecorino, aged under chestnut leaves for a rich, smoky flavor. Choose between two ride options:

Short option: 35 km (22 miles), +613 m (2011 ft) elevation

Long option: 52 km (32 miles), +777 m (2549 ft) elevation

Start your day with a scenic ride along the ridgeline of the bare clay hills north of Pienza, where cypress trees mark the entrances to isolated Tuscan farms. Stop for a cappuccino in the charming village square of Trequanda before continuing your journey through the Asso River Valley and its surrounding vineyards. Head toward the historic hilltop town of Montalcino, once home to Sienese nobles, and now famous for its world-renowned Brunello di Montalcino wine.

Today's scenic route starts with a visit to the Abbey of Sant Antimo, a stunning 8th-century landmark. As you ride on, enjoy panoramic views as you climb to Castiglione d'Orcia and descend into the beautiful Orcia Valley. At the valley's base, take a second chance to explore Bagno Vignoni, a picturesque village known for its thermal baths. Cycle through San Quirico d'Orcia, a key stop along the Via Francigena, the ancient route linking Rome to northern Italy. End your ride with a climb up to Montalcino.

Options:

Short ride (S. Antimo & back): 22 km (14 miles), +370 m (1214 ft)

Long ride (through San Quirico & Bagno Vignoni): 55 km (34 miles), +1144 m (3753 ft)

Today, you'll experience the full beauty of Tuscany as you leave Montalcino and pedal towards Siena. The landscape transitions from the lush green fields and forests of the Orcia Valley to the striking barren clay hills of Central Tuscany. Along the way, pass by the historic Monastery of Monte Oliveto Maggiore and ride through the eroded chalk hills of the Crete Senesi. As you enter Siena, you'll be transported back in time. This medieval city, once a powerful rival to Florence in the 1300s, remains one of Italy's best-preserved cities.

After breakfast, your Tuscan adventure comes to an end, but Siena is worth an extra day or two to explore. With frequent and fast trains, you can easily travel to Florence or head south to Rome.