Challenge Tuscany bike tour

Arrive on your own to Pienza, the most perfect Renaissance town in the world. Meet & greet, bike-fitting session OPTIONAL short ride to Montepulciano and Monticchiello 35 km

Today we'll start out on a long descent into the rolling green pastures of the Val d'Orcia: You are now at Parco Naturale e Artistico della Val d’Orcia, an Unesco site with this main justification: “ The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures.” Imagine cycling up and down in a scene from painting...
Bagno Vignoni: The ancient village is located in the heart of Tuscany, in the Val d'Orcia Natural Park. Thanks to the Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), these thermal waters were found and have been used since Roman times. The heart of the village is the "Square of sources", namely a rectangular tank of 16th-century origin, which contains the original source of water that comes from the underground aquifer of volcanic origins
Along the way face the hearty uphill to Castiglione d'Orcia, with the imposing Rocca A Tentennano. After a rest, enjoy a long downhill to Sant'Antimo Abbey , your next stop: if you have luck, you will hear the monks chanting. On your way to the Etruscan village and wine town of Montalcino you’ll pedal through magnificent vineyards. It is a fortified town which was used as a shelter by Siena nobles during the 16th Century. Today it is even more famous thanks to the production of one of Italy's premier fine red wines, Brunello di Montalcino. Back to Pienza via San Quirico d’orcia: stop in the village at Horti Leonini Garden, the top attraction of town.
Total Distance 68 km/42 miles available longer ride via San Filippo and Abbadia 100km

Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. Following a picturesque road, you’ll ride by Castelmuzio, Trequanda. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands, with strange rock formations and lone farmhouses flanked by twin cypress trees. 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. Cycle in the valley for a while and reach Lucignano, a small village that represents one of the more extraordinary examples of medieval urban planning for its system of elliptic rings arrived intact over the centuries. Destination is a real castle restored – its magical!
Total Distance: 57 km/35 miles. Available extension via Asciano

Pedaling north, we'll whisk past a pair of typical southern Tuscany towns and make a stop at Castelnuovo Berardenga, the gate to Chianti Classico region, then pass through the vineyards, continue to Castello di Brolio winery, home of Barone Ricasoli and his world-renowned wine. Few miles more and we’ll get in Gaiole; stop in the village for a light lunch. Now face the climb to Badia a Coltibuono thinking only you will enjoy the beautiful downhill to Radda in Chianti. Now last 10 km up and down and get to your palazzo hotel with a spa. Before dinner we will be treated a terrific Chianti Classico wine tasting in a small winery.
Total Distance 64 km/40 miles - available extension to Monte Luco

Ride to San Gimignano: more vineyards await us today, but you'll be amazed at how different they look once we get into the district of San Gimignano. Soon you pass 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. Soft, colorful, rolling hills of vineyards and sunflowers provide the backdrop to pre-Roman Etruscan remnants on your route to San Gimignano’s "medieval skyscrapers” in the distance you will see the seventeen towers. You'll have plenty of time to wander through the cobblestoned streets, window shop and buy a few last-minute Tuscan mementos for our friends and...why not, for ourselves too!
Total Distance: 60 km/37 miles

Today, you will leave San Gimignano behind and cycle to the ancient Etruscan town of Volterra. Through a patchwork-like landscape dotted with wheat fields, olive groves and villas, you reach the base of the imposing hill upon which the town is set. One more solid climb before you arrive in the old town. The “magic and mysterious” city of Volterra has its roots in three thousand years of history. It is possible to find evidence and traces from every historical period which gives the artistic city a unique aspect.
Total Distance 60 km / 37 miles