Meet your guides at 9:30 in Florence this morning for a bike fitting and the start of your first ride. We know the city well, so have a great way to get out of town and into the Chianti hills while avoiding the city traffic. Our destination is the village of Panzano in Chianti, where we stay at the hotel Relais Fattoria Valle (or similar), a beautiful 18th-century Tuscan manor house. Once home to a noble Florentine family, it has been restored and transformed into a lovely country hotel. The views from the garden and pool area are gorgeous, and it’s a great place to kick back and relax after a challenging day of riding the Tuscan hills. We dine in the hotel garden beneath a leafy canopy of plane trees. Overnight near Panzano. Hotel and dinner included.

Today we explore the hills and historic villages of Chianti, beginning with Radda, one of the cities in the Chianti League that helped Florence defend its territory from the Sienese during the Middle Ages.  After a coffee break and some window-shopping, we continue on to Gaiole where we have lunch in the main square. Stop for a visit to a local ceramics producer on the way home, then return to your hotel.  Late this afternoon we will visit the winery of Fattoria Le Fonti, a small, family-owned boutique winery owned and operated by my friends Guido and Vicki. After this special visit, we will have dinner nearby. Overnight near Panzano. Hotel, breakfast and dinner included.

Today’s ride takes us through the tiny hamlet of La Piazza and then on to Castellina in Chianti for a mid-morning cappuccino. Your uphill efforts are rewarded by a fantastic downhill into the valley below. We stop for lunch at a local trattoria with a fabulous choice of pasta dishes and salads. We then ride to Siena and check into our hotel, La Colonna (or similar), which is situated just outside the medieval city walls and has a pool. We’ll have a visit of the city in the late afternoon, and then you are free to dine as you like tonight since it’s a “free night.” Overnight Siena. Hotel and breakfast included, dinner not included.

This morning we bike into a terrain that is completely different from what we have seen so far, and enter the clay hills of the Crete Senesi. Those who have seen the films Stealing Beauty or The English Patient will recognize this starkly beautiful landscape of barren rolling hills punctuated by solitary cypress trees. We first stop in the charming and authentic village of Asciano, an ancient walled town whose inhabitants have ingeniously incorporated the old defensive walls into their homes. After lunch, we bike to our hotel, the Hotel Casabianca (or similar), a beautiful 4-star hotel in a renovated manor house featuring a lovely garden and gorgeous swimming pool. Relax by the pool and then meet up again for dinner. Overnight at the Hotel Casabianca. Hotel, breakfast and dinner included.

Today we have a loop ride to the beautiful Benedictine Abbey of Monte Oliverto Maggiore, whose monks are famous for their erudition and strict vows of silence. Visit the frescoed cloister and then enjoy a coffee in the garden before continuing on to lunch in the medieval village of Montisi. Optional extension ride or return to the hotel and enjoy some down-time by the pool or in the shady garden. Overnight at the Hotel Casabianca. Hotel, breakfast and dinner included.

Today we ride through the dramatic landscapes of southern Tuscany to the Renaissance gem of Pienza. The town was designed between 1459-62 following a decree by Pope Pius II in which Pienza was to become a showcase for Renaissance architecture and as such it boasts one of the earliest Renaissance cathedrals in Tuscany. It is also the heart of the local pecorino cheese production which goes so well with a glass of Vino Nobile from neighboring Montepulciano!  On our way to Pienza we stop for lunch at the unique village of Bagno Vignoni, whose thermal springs have been treating Tuscany’s nobility for centuries. Our hotel will either be the four-star Relais Il Chiostro (or similar), a renovated cloister located inside the city walls with spectacular views over the countryside, or the recently restored Hotel Corsignano (or similar), just outside of the city walls. Dinner together in a local trattoria.  Overnight Pienza. Hotel, breakfast and dinner included.

Our final day of cycling in Tuscany ends with a fantastic ride that takes us to the hilltop towns of the Orcia Valley. A sweeping downhill (and then uphill!) takes us to the lovely walled hamlet of Montichiello, where we can stop for a coffee break and enjoy breath-taking views over the valley.  We then continue on to Montepulciano. Founded by the Etruscans 2,500 years ago, it continued to be a vital and important city well into the Renaissance. It sits high on a hilltop, so was the perfect location for the Medici to expand their power into south-eastern Tuscany. We have lunch here, and you have time to explore the main squares, back alleys and shops before we meet up again to continue our ride back to Pienza. Tonight we get together for a final aperitivo and dinner together in town. Overnight Pienza. Hotel, breakfast and dinner included.

9:00 transfer to Chiusi for 10:00 trains to Rome, Florence and beyond. Breakfast and transfer included.

The biking in Tuscany is hilly! We sometimes ride sustained climbs of 10-15 kms, with some steep grades. We ride 40 – 65 km a day, with optional extensions as well as van support, which allows you to relax off the bike for a while. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or explore the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region.

The City of Florence: everything you need to know about the city.
The Accademia:  home of Michelangelo’s David and other world-famous works and The Uffizi Gallery: one of the greatest collections in the world. We recommend you make reservations ahead of time. The official site for both the Uffizi and Accademia is http://www.polomuseale.firenze.it  and http://www.Uffizi.org where in addition to ticket reservations useful information about the museum the artworks, the events,
and what visitors need to know before visiting the gallery.
The Duomo: one of the wonders of the Renaissance, Florence’s cathedral.
Siena: this site has interesting links to areas within Siena province, like Chianti, the Val d’Orcia, & the Crete Senesi
Chianti Classico wine corsortium: a site devoted to this world-renown wine and its group of producers
Monteriggioni: more information on this fascinating hilltop fortress
UNESCO World Heritage Sites: Italy has more sites listed than any other country!