The easiest way to get to Montepulciano is to take the train to Chiusi and transfer to a bus to Montepulciano. Those of you on the pre-tour package in Rome will have an OutWest trip leader with you. OutWest will provide detailed instruction on how to get to meet up with the group.
Accommodations: Il Marzocco

DAY TWO.  RIDING THROUGH WINE COUNTRY.  The Tuscan countryside is a patchwork of hay meadows, pastures with grazing sheep and cattle, fields of wildflowers, and quaint farmhouses. On the bike ride from Montepulciano we’ll go through the villages of Pienza and Bagno Vignoni.You’ll experience this pastoral setting as you pedal between villages with stops to enjoy food and drink. That afternoon we’ll be back in Montepulciano.
Accommodations: Il Marzocco

DAYS THREE AND FOUR.  CORTONA Today’s route brings us from the hilltop town of Montepulciano across a wide valley with relatively flat terrain, to the hillside town of Cortona. The Etruscans settled this town in the 8th century BC and the Romans later moved in. Like many Tuscan towns, a walking tour will bring us through piazzas, a Romanesque cathedral, and small pedestrian alleyways. We’ll be two nights in Cortona.

The second day in Cortona will feature riding around Trasimeno Lake, the fourth largest lake in Italy. Along the way, you can stop to visit a 13th century palace, take a stroll along one of the village promenades, stop for a drink at an outdoor café, or take a swim in the lake to cool down.
Accommodations: Hotel Corys

DAY FIVE.  UMBRIA: BEVAGNA. After transferring by van to the walled city of Assisi, we’ll make a stop to tour the town’s main plaza, cathedral, and roman ruins. The town is best known for being the home of St. Francis of Assisi. The bike journey will bring us along a route that borders a protected natural area. Our final destination is the small town of Bevagna.
Accommodations: Hotel Brunamonti

DAY SIX.  SPOLETO Best known for its Roman ruins, museums, and theater performances, Spoleto is a famous Italian cultural destination. Our biking route will bring us through the countryside and vineyard, to this city of 37,000 people.
Accommodations: Hotel Clitunno

DAY SEVEN.  ARRIVEDERCI!  This trip ends in Spoleto where you can take a train to Rome (1 1/2 hours) or Florence (2-3 hours) or other parts of Italy. Ciao!