Day 1: Arrival
We meet in Assisi. Join us for a Welcome dinner. Airlines from a variety of European cities fly into Perugia and the airport is close to Assisi. Trains from Rome, Florence and Milan service Assisi. Overnight in Assisi.
Day 2: Assisi Loop
Morning bike fitting followed by a lovely bike loop ride. Enjoy the back road to Spello, a perfectly preserved town with Roman origins. A visit to Bevagna, another wonderful medieval village & a special wine tasting are afternoon highlights. Ride: 45 kms
Overnight in Assisi.
Day 3: Assisi – Poggiolo
Our route through Umbria is highlighted by a visit to Deruta, a town famous for its ceramics. Ride: 52 kms
Overnight in a special villa in Poggiolo. Tonight will be one of the best dinners of the trip. We’ll go to a nearby farmhouse of one of our friends who was a chef in a restaurant.
Day 4: Poggiolo – Cortona
A curvy road will lead us to Lake Trasimeno whose shores teem with migratory birds. We’ll cycle near beautiful olive groves to Cortona, the setting for Francis Mayes’s best seller, Under the Tuscan Sun. Ride: 55 km
Overnight in a wonderful hotel just a stone’s throw from the Piazza.
Day 5: Cortona – Montepulciano
Today we 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 at Villa Cicolina.
Day 6: Montepulciano
Today most folks will enjoy spending the entire day visiting Montepulciano. Our guide will take us on a tour of the city including the underground channels, wine tasting options, Duomo, multiple Piazzas.
You can also opt for a morning loop ride to Montefollonico, a lovely 12th century hilltop town. We’ll also reach Montepulciano by lunch, where we’ll have time to visit the town and can also sample the Vino Noble wines in many of the local wine shops.
We’ll return in time to enjoy an afternoon swim and relax in our amazing villa. We return to our same lodging near Montepulciano. Overnight in Villa Cicolina
Day 7: Montepulciano – Bagno Vignoni
Today we ride an amazing Cyprus lined downhill to Monticchiello, climb to Pienza for lunch, descend to San Quirico and continue to our lodging near Bagno Vignoni, a famous Roman spa town. Ride: 50 km
Our lodging is a romantic country inn that is a finely restored 16th century horse and carriage station. Overnight in Bagno Vignoni.
Day 8: Bagno Vignoni to Montalcino
Our final ride takes us to the gorgeous abbey of Saint Antimo, a well preserved 12th-century church that still echoes with Gregorian chants. We finish our ride among the vineyards en route to Montalcino, a 13th century paradise and the home of Brunello wine. Our ride is shorter today and we plan to arrive in Montalcino at lunch time, so you will have plenty of time today for shopping and sampling some of the fine Brunello wines. Ride: 30 km
Overnight in Montalcino.
Day 9: Departure
After breakfast, we will transfer you to Siena where there is good train access to all of Italy. Siena is a wonderful city and worth spending a night if you have the time.