Self-Guided Biking Vacation in Tuscany
Destination: Italy
Activity: Bicycle Touring, Cultural Tours, Art/Architecture
Duration: 8 days
How Tough? Moderate
When? March-November
For Kids? For Adults Only
This self-guided, eight-day cycling tour explores the classic Tuscan countryside that is as beautiful as the picture books protray it.
You have the freedom to cycle at your own pace, with support behind the scenes. You have a set itinerary, pre-paid accommodations, luggage transfers and emergency support if you need it.
You begin your journey near San Gimignano, whose towers and rollercoaster hills beckon with the promise of breathtaking views.
You continue to Siena, rich with red brick. The frescoes, as beautiful as the scenery, adorn country abbeys and churches, especially Monte Oliveto Maggiore.
The 12th-century monastery of Sant’Antimo nestles in the arms of a quiet green valley, romantic in the moonlight. Montalcino stands high above the vineyards producing the celebrated Brunello wine.
Next, you continue on to Montepulciano, where enoteca (wine tasting boutiques) sit aside pretty squares and grand palaces.
Or, on this independent bike adventure, you can choose a harder tour and head south away from the tourists to an ancient land of volcanic rock, thermal cascades of steaming water and mysterious Etruscan tombs.
Your average daily distance is 30 miles (48 km). This is a hilly region with many climbs of moderate difficulty throughout the day.
You spend two nights in two locations, so you can take time off from cycling on some days.
Tour Plan
Tuscany Biking Itinerary
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. (26 miles/43 km)
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. (28 miles/36 km)
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. (23 miles/37 km) Your agritruismo is just 2 miles/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. (22 miles/36 km)
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. (18 miles/30 km)
Day 7: 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. (30 miles/48 km)
Day 8: Stroll around Montepulciano before departure.
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