Day 1: Pienza
Meet and greet in Pienza, the purest reniassance town in the world, for welcome and bike fitting. Pienza is a remarkable example of reniassance-era town planning. If you have even the least appreciation for beautiful architechture, it's a real treat to stroll around it's cobblestone streets. Take an optional test ride to San Quirico d'Orcia (13 miles/20 km).
Overnight in Pienza
Day 2: Pienza – Montepulciano and vino nobile (34 miles/55 km)
Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.
Overnight in Pienza
Day 3: Pienza – Montalcino brunello land (29 miles/46 km)
Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, 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 destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked.
Overnight in Montalcino
Day 4: Montalcino – Siena and Monte Oliveto Abbey (36 miles/58 km)
Today will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. Following a picturesque crest road, you’ll ride by Monte Oliveto Maggiore Abbey, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere.
Overnight in Siena
Day 5: Siena – Chianti hills (31 miles/50 km)
Ride from Siena to Castellina in Chianti, following the "Chiantigiana" road. Along the way you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlet. Not far away is Castello di Brolio, a castle and winery that you can visit. There's also the chance to shop at a first-class ceramics workshop. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get to Castellina.
Castellina's medieval street, the Via delle Volte, was originally open to the sky, but over the years houses and shops have encroached on the ancient city walls, covering the street and providing an intriguing underground home for shops and restaurants.
Overnight in Castellina in Chianti
Day 6: Castellina – Greve in Chianti and Panzano (34 miles/56 km)
Circular bike ride to Florence chianti: bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany's forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honeys and rich olive oil. Have a stop at Greve's main piazza, characterized by an original formation of irregular triangular shape, defined by beautiful long porticos. Back via Panzano with preserved the old walls, gate and the keep of the medieval castle. relax by the vanishing edge poolspilling into the countryside of endless vineyards.
Overnight in Castellina
Day 7: Monteriggioni (optional 20 mile/32 km loop ride)
The short bike ride allow you to visit Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around.
