Day 1: Arrival
We meet in Cortona. Join us for a Welcome dinner. Book your flight into Florence or Rome and and there is good train service from both cities to the start of the trip. Cortona, the setting for Francis Mayes’s best seller, Under the Tuscan Sun and a beautiful hill town to begin our tour.
Overnight in Cortona.
Day 2: Cortona – Montepulciano – Ride 50 km
Today we will ride 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. We’ll settle into one of our favorite villas outside of Montepulciano for 2 nights.
Overnight at Villa Cicolina.
Day 3: Montepulciano – loop ride 40 – 60 km
In the morning we will enjoy a 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. Our guide will take us on a tour of the city including the underground channels, wine tasting options, Duomo, multiple Piazzas.
We’ll return to our lodging in the late afternoon with time to swim and relax in our amazing villa. We return to our same lodging near Montepulciano. Overnight in Villa Cicolina
Day 4: Montepulciano – Bagno Vignoni Ride 50 km
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.
Our lodging is a romantic country inn that is a finely restored 16th century horse and carriage station where we will spend 2 nights. Overnight in Bagno Vignoni.
Day 5: Bagno Vignoni loop ride 60 km
Our loop ride today is one one of the most beautiful in all of Tuscany! We ride to the gorgeous abbey of Saint Antimo, a well preserved 12th-century church that still echoes with Gregorian chants. We continue to Montalcino riding past the vineyards of the famous Brunello wines. We will have lunch in Montalcino before returning back to our villa in Bagno Vignoni.
Day 6 – Bagno Vignoni – Siena – ride 60 km
The road winds through hills and oak woods to Monte Oliveto Maggiore, the most impressive abbey in Italy. We’ll finish the ride with amazing vistas of the crete landscape and then it’s on to Siena, our 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. We’ll have our farewell dinner near the famous Campo piazza in Siena.
Overnight in Siena.
Day 7 – Departure
Your tour ends after breakfast. There are both train and bus stations in Siena with easy access to both Rome and Florence.
Siena is a wonderful city worth spending an extra night if you have the time.