Day 1: Welcome to the Villa
Meet at the Chiusi train station (a major stop on all the Rome-Florence lines) at 1:00pm. Private van transfer to the country house Palazzi del Papa, just a short drive from Pienza. Check into your room and start the bike-fitting session and meet your guides. After all guest are set with bikes and equipment we'll have a short test bike ride in the valley.
Then get ready for your first cooking session with Paola – a perfect way to build the team. You'll enjoy this hands-on lesson: preparing fresh pasta as primo piatto, appetizer, tiramisu; after a rest with a prosecco sparkling wine as aperitif, we'll share the table with all guest and savor the welcome dinner.
Day 2: Cortona (28 miles/45 km)
After a welcome breakfast, we'll have a short transfer by van to just outside Montepulciano village to begin the first ride with a nice gentle downhill through the vino nobile vineyards. After this will be flat terrain--the Val di Chiana, once a swampy lowland--except for the final climb to reach the old town on the hill Cortona, one of Italy's oldest towns.
The first set of city walls were built by the Etruscans in the 4th century BC. Cortona became famous by Frances Mayes's bestselling book (also a movie), "Under the Tuscan Sun." Stroll the winding – narrow and steep! – medieval streets for a while.
Transfer back to the country house by van in the afternoon (or stronger cyclists have an option to ride back)! Dinner in Monticchiello at La Cantina della Porta.
Day 3: Pienza, Montepulciano (29 miles/46 km)
Our ride today starts from the villa. The first stage is Pienza, a pristine Renaissance jewel, founded in 1458. Pope Pius II chose the famous Florentine architect Rossellino to transform his home village of Corsignano into one of the few examples left of 15th century architecture. The main product in this area is the pecorino cheese, a delicious, pungent cheese made using only sheep milk.
You'll continue to next village Montepulciano, known as the Pearl of the 16th Century. After lunch at la Porta di Bacco, you'll see some Etruscan caves and enjoy a wine tour at Cantine de Ricci and explore the underground wine cellar. This Cantina is right in the center of town just off Piazza Grande, and has been dubbed the most beautiful wine cellar in the world.
Back in the saddle, the last stop is the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the Orcia valley where we bike through the fields that inspired Renaissance painters. Tonight you'll have dinner at Locanda in Tuscany.
Day 4: Montalcino and Brunello (30 miles/48 km)
Our ride starts from the villa: first stop after 10 km easy ride is the ancient Roman spa of Bagno Vignoni. Legend has it that Saint Catherine and Pope Pius II both bathed in the thermal waters here. The water has a constant temperature of 51 degrees Celsius (124 degrees Fahrenheit). At the heart of the village is the "Square of sources," a rectangular tank of 16th-century origin, which contains the original source of water that comes from the underground aquifer of volcanic origins.
Now the climb to Castiglione d’Orcia is the challenge part of the day. Once at the top, enjoy a long downhill till Romanesque abbey of Sant’Antimo that dates back to the time of Charlemagne. The final effort is 9 km gentle ascent to Montalcino – the hill town famous for Brunello wine made with the Sangiovese Grosso grape and aged a minimum of four years. After the visit we'll reach the Corte Pavone winery: you will taste this biodynamic and organic Brunello wine, learn about the aging process, and enjoy the lunch at the cellar. Return to the villa for the second cooking lesson.
Day 5: Radicofani and Pici (34 miles/55 km)
Today another terrific bike ride. Start from the villa and reach Radicofani, a medieval and enchanting village with one of the most impressive fortresses in Tuscany. Radicofani is included in the Park of val d’Orcia – a Unesco site and Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), but still is off the beaten path. This will be the quietest day.
From Radicofani now we will ride another secluded road called le Conie and reach Bagni San Filippo. Enjoy the downhill back to the valley. The valley rises along Francigena road near the old Spedaletto Castle, shelter for wayfarers who, in the Middle Ages, wanted to get to Rome from all over Europe. The castle was readapted in a granary, a real fortified farm.
We'll head back to the country house by bike. This afternoon let's learn the classic pasta of the area: pici all’ aglione sauce and pici al ragu di chianina. Pici is a fresh spaghetti, handmade one by one.
Day 6: Siena (38 miles/60 km)
After breakfast ride toward San Quirico, an Etruscan origin village with a superb Italian garden: the Horti Leonini. Pass through Asciano and Le Crete with strange rock formations and lone a farmhouse flanked by twin cypress trees.
Let's pedal through vineyards and forest and arrive in Siena, a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. Visit the shell shape square where the Palio horse race is run and enjoy lunch on your own. Back to the villa, you'll have time for a jump in the pool and a rest. We'll have our farewell dinner at a restaurant at la bandita townhouse.
Day 7: Individual departure
After a farewell breakfast all together, we will transfer you to the Chiusi train station around 10-11:00am. (On request we will arrange transfer at different time.)