Tuscany Bicycle Trip Itinerary

A bike tour in Italy is heaven...on a stretch where town and country, sunlight and seascape exist in spectacular harmony, one will be struck by the near certainty that here lies the most perfect spot on Earth. Tuscany.

Tuscany Day One & Two: Bicycle to Montepulciano Vino Nobile
Enjoy a loop ride around Pienza, an architectural gem of Tuscany. This area is so spectacular, you'll feel like you are on a movie set.  Bicycle the lovely Val d'Orcia stopping at Monticchiello, Montepulciano, Castelmuzio. Taste fabulous wines, Brunello di Montalcino and Vino Nobile di Montepulciano, and some of the region's pecorino cheese. Take time to meander on the cobbled streets of Pienza, sit at a café, and people watch. After a delicious dinners comprised of regional favorites, we'll spend the two night in Pienza/Montepulciano.

Tuscany Day Three: Bicycle to Montalcino Brunello
Today's cycling route is one of the most beautiful rides in Tuscany. We begin with a downhill stretch that affords a breathtaking view of Mount Amiata, the highest peak in Tuscany, and a glimpse of the imposing tower of Radicofani. We meet outside of Montalcino for a delicious picnic lunch. In the afternoon, enjoy free time in Montalcino, a picturesque town famous for Brunello wines and medieval architecture. This evening, we'll enjoy another classic meal at our villa.

Tuscany Day Four: Bicycle to Siena Piazza del Campo
Today you will spin through the Crete Senese, pass the Abbey of Monte Oliveto Maggiore, and view the Renaissance frescoes at the monastery.  After an invigorating ride, we'll enjoy a home-style lunch at a local trattoria.  In the afternoon we'll arrive in Siena, a consummate medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. The piazza was designed to be work of art in itself, blending into the stunning surrounding landscape. Here you'll have time to shop while exploring the many hidden medieval walkways.

Tuscany Day Five: Bicycle trip to Chianti Classico
Ride deep into the hills of Chianti past rows of olive trees and tall cypress. Bike past vast stretches of beautiful vineyards – this is the birthplace of the famous Chianti Classico red wine. Pedal along winding panoramic roads to towns Radda and Castellina. In Castellina we enjoy a private tasting of Chianti's best wines. After dinner, climb into bed at our abode for the night, Villa Casalecchi.

Tuscany Day Six: San Gimignano
Shuttle through the stunning Tuscan countryside. We'll soon arrive in the 14th-century village of San Gimignano, which once bristled with 76 towers. Today, only 13 towers remain in this stunning city known for its art, architecture, and saffron. In San Gimignano we say goodbye to new friends made and reflect on our DuVine Tuscany adventure!
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Your bicycle trip itinerary in Italy provides deluxe cycling including gourmet food, authentic italian wine tastings and luxury tuscany accommodations for your bicycle tour.