Experience the Cortona to Siena Cycling Tour, a breathtaking self-guided bike tour through the heart of Tuscany. Ride past rolling vineyards, medieval villages, and stunning landscapes, including the UNESCO-listed Val d'Orcia. This cycling holiday offers the perfect balance of exploration and relaxation, with multiple two-night stays to immerse yourself in Italy’s rich history, culture, and cuisine. Pedal through charming hilltop towns like Cortona, Montepulciano, Pienza, and Montalcino, discovering their Renaissance architecture, local wineries, and artisan shops. Savor Brunello di Montalcino, Vino Nobile, and traditional Tuscan dishes as you cycle through iconic landscapes. From the shores of Lake Trasimeno to the medieval streets of Siena, each day offers scenic rides, historical landmarks, and unforgettable experiences. Whether you're cycling past cypress-lined roads, historic abbeys, or picturesque farmhouses, this Tuscany bike tour is an unforgettable way to explore one of Italy’s most spectacular regions.
Arrival in Cortona
Loop ride to Trasimeno Lake and surrounding hills
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Bicycle to Montepulciano and Pienza
Loop ride in the Orcia Valley
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Bicycle to the wine town of Montalcino
Loop ride to Bagno Vignoni and the Abbey of Sant Antimo
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Bicycle to Siena
Departure
Hotel
