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Tuscany Cycling: Self-guided TourTour Duration :
8 Days  Day 1:
Transfer from Poggibonsi to Staggia. A wonderful villa and a splendid dinner await you. Day 2: Pedal into the rolling countryside to Colle di Val d’Elsa, a medieval gem famous for glass-blowing. Continue to San Gimignano, once known as the “city of beautiful towers”, with one of the most striking skylines of any Italian town. Then wind your way among vineyards and olive groves back to Staggia. (43 km/26 mi) Day 3: Ride to delightful Castellina in the heart of the Chianti wine region. Then it’s on to Monteriggioni, a 13th-century fortress town still encircled by high walls with heavily fortified watchtowers. Today’s destination is Siena, one of the most beautiful cities in Italy. Stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for dinner. (36 km/28 mi) Day 4: Leave the vineyards of Chianti for the primeval landscape of the crete senesi . Visit tiny Murlo, the oldest settlement in the area, before arriving at Buonconvento, a delightful little town with imposing walls. (37 km/23 mi) Your agritruismo is just 3 km outside of Buonconvento. Day 5: Head into the spectacular eroded hills of the crete and through thick cypresses and olive groves to the 14th-century Benedictine monastery of Monte Oliveto Maggiore. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. Then continue to Montalcino, a classic Tuscan hilltown renowned for its ruby-red Brunello wines. (36 km/22 mi) Day 6: A highlight today is the abbey of Sant’Antimo, set in a peaceful valley south of Montalcino. Its 12th-century church is well preserved and is an outstanding example of the Italian Romanesque. It still echoes with Gregorian chants when the monks are at their devotions. Then a spectacularly scenic road leads you back to Montalcino. (30 km/18 mi)
Today is filled with wonderful sights. Pause at the hot sulfurous pool in the piazza at Bagno Vignoni, then continue to Pienza, a Renaissance jewel redesigned by Pope Pius II. Pause for an espresso in Montichiello, a tiny walled village, then head for beautiful Montepulciano, one of Tuscany’s highest hilltop towns and famous for its Vino Nobile. (48 km/30 mi) Day 8: Stroll around Montepulciano before departure.
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