Terms & Conditions Apply
This cycling trip captures the essence of glorious Tuscany, starting the tour by staying at the beautiful Villa Marsili, in Cortona. You will discover Montepulciano, Pienza, Val d’Orcia and the Crete Senesi.
The mystique of this land lies not only in its landscape, but also in its nature, its vineyards and its history: oak woods, olive groves and vineyards watch over enchanting hillsides, medieval villages and historical monuments. Each day you rise, enjoy a good espresso or cappuccino, cycle for five or six hours in the fresh air and spend the night in a warm, welcoming inn.
Nice to meet you! Transfer from Chiusi station to the charming Villa Marsili followed by a bike-fitting session. You are then free to explore this delightful town, made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun.
Welcome dinner at Le Loggette in the main square.
Ride to Valle di Pierle. The history of Val di Pierle is closely linked to the history of the splendid castle (la Rocca) that dominates the valley. The castle was built prior to the 10th century and belonged to the marquises of Monte Santa Maria Tiberina. Another climb and you will reach the top of the hill (Cima di Tuoro) from where you will be able to enjoy a stunning view of the Lake and its islands. From the top enjoy the lovely downhill to Tuoro sul Trasimeno. You are in the Umbria region now and in Tuoro you can stop in the village at the beach. On the saddle again and back to Cortona on gentle terrain!!
Total distance: 52 km/32,5 miles
Ride from Cortona to Montepulciano. This splendid little town, whose artistic and architectural heritage led it to be called the Pearl of the Cinquecento, has preserved its beauty intact. Going up the steep streets of its outlying districts you will discover beautiful palazzos and churches. Back in the saddle and after 15 km let’s stop in the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the Orcia valley where you will bike through the fields that inspired Renaissance painters. Il Chiostro di Pienza is housed in a 15th-century convent in a quiet, secluded location right in the centre of Pienza – itself a rare masterpiece: entirely rebuilt between 1459 and 1462. In the evening you will enjoy a gourmet dinner at your hotel La Bandita Townhouse.
Total distance: 60 km / 37,5 miles
Circular bike ride into Orcia valley: for the first 15 km of the ride you will glide downhill among the gentle, rolling hills. . A gentle climb is needed to the enchanting medieval village of Radicofani, with a Rocca dating back to 1200. After a stroll around the stately old town, we’ll head back into the country, along some of those winding cypress-lined roads. On the way back we will have a “pecorino” sheep milk cheese tasting at Pianporcino organic farm followed by dinner in town.
Total distance: 66 km / 41 miles
First we pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe, then push on to the monastery of Sant’Antimo, where you might catch one of several vesper services performed each day by the monks.
The famed wine town of Montalcino is your highlight: visit the fortress to see a breathtaking view of the entire valley you’ve just cycled through . Back in the saddle and enjoy the long downhill and flat paths to reach the winery. Lunch at the cellar and Brunello wine tasting. Back to Pienza by bike or by van. Dinner at Dopolavoro at la Foce.
Total Ddistance: 68 km / 42,5 miles
Enjoy the downhill from Pienza, first stop Giovanni d’Asso The ancient Borgo of San Giovanni d’Asso famous for its valuable white truffle, is rich with farms, hamlets and castles reminiscent of the colors of the paintings of the Renaissance. On the way you’ll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings. Next, you’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands. Your destination is a charming resort between the town of Siena and the Chianti wine region.
Total distance: 66 km / 41 miles
Arrivederci – end of bike tour – explore Siena on your own before you reach the train station for your next destination in Italy.