2025 CLASSIC TOUR OF TUSCANY

Itinerary

Day One: Welcome to Tuscany and Cortona / Welcome Dinner
Begin your journey in Cortona, the iconic medieval town celebrated in “Under the Tuscan Sun” and “Life is Beautiful.” Its cobblestone streets, lined with cozy cafés and boutiques, lead to stunning views over the Tuscan landscape. Upon arrival, a shuttle will take you to your four-star hotel where our team will ensure your bikes are a perfect fit. Tonight, dinner is your chance to explore Cortona’s culinary delights on your own, savoring the start of your Tuscan adventure.

Day Two: Castiglion del Lago Loop
Embark on a 10km scenic ride to Castiglion del Lago, nestled above Trasimeno Lake. Explore the village's castle and historic center, rich in shops and boutiques. For lunch, try a "tagliere con formaggi e salumi" or the traditional "pici" pasta, embodying the area's flavors. Consider a visit to Baldetti Winery for a reserved tasting of wines, bruschetta, olive oil, and pecorino cheese, enhancing your return trip. Finish the day with a 12km ride back to Cortona, with dinner on your own to discover more local tastes.

Day Three: Cortona to Pienza
Embark on a captivating bike ride through Siena's enchanting province, starting with a thrilling descent from Cortona and culminating in a challenging ascent to Pienza. Choose your adventure: the shorter route offers a gentler climb but skips the medieval charm of Montepulciano. Both paths converge in Torrita di Siena, a quaint village en route to Pienza, 15km away. Pienza, once known as Corsignano, transformed under Pope Pio II into an ideal Renaissance town, marking the dawn of urban planning. Its central square, flanked Savor the journey with a taste of Pecorino Toscano, a hallmark of Pienza's culinary tradition. Whether aged or fresh, this savory sheep's cheese is a delight. Opt for the longer route to explore Montepulciano's historic walls and indulge in the renowned Vino Nobile, a testament to Italy's rich winemaking heritage. This ride isn't just a journey through Tuscany's landscapes but a voyage through its cultural heart and soul.by majestic buildings, led to its UNESCO World Heritage status in 1996.

March 9: Strade Bianche Gran Fondo!
Today is your opportunity to test yourself on the famed gravel roads of Toscana during the Gran Fondo Strade Bianche! The route is as beautiful as it is challenging! After the final ascent up the challenging Via Santa Caterina in the center of Siena, you’ll experience on the greatest finish lines in all of sport - the Piazza del Campo! This afternoon, relax at our villa while savoring the week and all of the adventures we’ve shared together before our “Farewell Dinner.”

March 10: Transfers / Extend Trip Option
After breakfast and a final cappuccino at the villa, we’ll organize transfers to the Florence Airport. Estimated time of arrival at the airport is 12 noon. If you drove to the villa, your trip will conclude with check-out at 12 noon.