Day 1 – Arrival
Our Italian representative will pick you up at the Assisi train station and transfer you to your first hotel. At that time they will give you a tour orientation and bike fitting. Overnight in Assisi.
Day 2 – Assisi Loop Ride: 45 Km
Enjoy the back-road to Spello, a perfectly preserved town with Roman origins. A visit to Bevagna, another wonderful medieval village. Overnight in Assisi.
Day 3 – Assisi – Poggiolo Ride: 52 Km
Our route through Umbria is highlighted by a visit to Deruta, a town famous for its ceramics. Tonight’s lodging is at Poggiolo, a beautiful old rural villa. Overnight in Poggiolo. Dinner Included.
Day 4 – Poggiolo – Cortona Ride: 65 Km
A curvy road will lead us to Lake Trasimeno whose shores teem with migratory birds. You’ll cycle near beautiful olive groves to Cortona, the setting for Francis Mayes’s best seller, Under the Tuscan Sun. Overnight in Cortona.
Day 5 – Cortona – Montepulciano Ride: 50 Km
Today you will enter Tuscany through the magnificent wine country of Montepulciano, one of Tuscany’s highest hilltop towns. Renowned for its Vino Nobile, Montepulciano also boasts a unique blend of Renaissance architecture and is perched on a narrow ridge of volcanic rock. Overnight in Montepulciano.
Day 6 – Montepulciano – Montalcino Ride: 50 Km
Traveling through Pienza, home of Pope Pio II, you’ll find a unique collection of palaces, churches and a charming square. This ride takes you through the Crete landscape, one of the most famous in the world: rolling hills in all shades of brown or green; sturdy brick farmhouses or imposing mansions crowning the hilltops and cypress lined alleys design a perfect scene that inspired painters since the Middle ages. You finish your ride among the vineyards en route to Montalcino, a 13th century paradise and the home of Brunello wine. You will enjoy a two night stay within the walled city. Overnight in Montalcino.
Day 7 – Montalcino Loop Ride: 50 Km
Our loop ride takes you to the gorgeous abbey of Saint Antimo, a well preserved 12th-century church that still echoes with Gregorian chants. There is plenty of time today for shopping and sampling some of the fine Brunello wines. Overnight in Montalcino.
Day 8 – Montalcino – Siena Ride: 53 Km
The road winds through hills and oak woods to Monte Oliveto Maggiore, the most impressive abbey in Italy. Then it’s on to Siena, your final destination. Siena is one of the most beautiful medieval cities in Italy. Its famous Piazza Del Campo is an open-air museum and architectural gem. Overnight in Siena.
Day 9 – Departure
Your tour ends after breakfast. There are both train and bus stations in Siena with easy access to both Rome and Florence.
** Shorter itineraries available.