Itinerary

Day 1: Meet in Torgiano, Umbria
Highlights: Fit bicycles and take a walk around town
Arrive today in Torgiano, famous throughout Italy for its wines. Take time to explore the comprehensive olive oil museum and the wine culture museum, the famous tower and the narrow alley ways. After fitting bikes you'll have time to go out for a short ride to Deruta, known internationally for its ceramics. In fact the classic Italian ceramic patterns will be familiar to you from many Italian restaurants in the U.S. We'll suggest a few studios you might like to visit. Back to the hotel we'll get together for introductions and a welcome dinner together this evening. Daily Mileage: 16km (10 miles).

Lodging: Hotel Al Grappolo d'Oro
Day 2: Loop ride to Assisi
Highlights: Bicycle to Assisi, guided visit of Assisi, Roman town of Spello
Our ride takes us across the Umbrian Basin to Assisi, home to Italy's patron saint, St. Francis. Assisi is a beautiful medieval town built on a hill overlooking a scenic valley. We'll have a guided visit to learn more about this fascinating town and then enjoy lunch together. Back on the bikes we'll ride to the Roman town of Spello with its impressive city gates and original Roman walls. We loop back to Torgiano later this afternoon. Dinner is on your own this evening. Daily Mileage: 50-60 km (31-38 miles).

Lodging: Hotel Al Grappolo d'Oro
Day 3: Bicycle to Cortona
Highlights: Etruscan city of Cortona, Etruscan Museum, Lake Trasimeno, scenic Tuscan countryside
We will leave Umbria today cycling through the picturesque landscapes that have made Tuscany Famous. Our first destination is the hilltop town of Magione with its castle, owned by the Sovereign Military Order of Malta, founded about nine centuries ago in Jerusalem with the aim of protecting the Holy Land. We'll continue along the shores of Lake Trasimeno, famous for Hannibal's defeat of the Roman army in 217 B.C. after crossing the Alps with elephants! Entering Tuscany we'll stay at the imposing town of Cortona looming over the valley with its defensive Etruscan, Roman and Medieval walls. Cortona is the ideal place to learn more about the Etruscans and their history. A must-see is the recently restored Etruscan Museum or the Museo Diocesano with Fra Angelico paintings. Cortona was made famous by Frances Mayes' book and movie, Under the Tuscan Sun. Dinner is together this evening. Daily Mileage: 70 km (44 miles)

Lodging: Hotel San Michele and Hotel San Luca
Day 4: Montepulciano, Val d'Orcia and Pienza
Highlights: Montepulciano, Pienza and Val d'Orcia, Tuscany
We'll pedal to Montepulciano and Pienza, home of Pope Pius II who, with the help of a number of renowned architects, turned this tiny village into a showpiece of Renaissance town planning in the 16th century. Our hotel tonight is just outside the city walls, overlooking the Orcia Valley, a pleasant and very relaxing spot. Take a walk around town, sample the local wines and cheeses (we highly recommend the Pecorino that is aged under ashes and wrapped in chestnut leaves). Dinner is together tonight. Daily Mileage: 60km (37 miles)

Lodging: Piccolo Hotel La Valle
Day 5: Loop ride across Val d'Orcia to San Casciano
Highlights: The World Heritage Landscape of Val d'Orcia, San Casciano thermal springs and historic town center
Wide stunning views await us today as we head south to the very heart of the Orcia Valley. The smooth and rounded hills change color with the seasons from bright greens and reds in spring to soft gold in summer and deep gray when the fields are ploughed in late fall. We pedal on to Bagno Vignoni, a Medieval spa with its hot spring, take a look at the old famous pool Vasca di Santa Caterina and soak your feet in the therapeutic warm water. Dinner is on your own tonight, there are several local restaurants and osterie that serve the typical homemade pasta; garlic lovers should try the pici all'aglione! Daily Mileage: 80-90 km (50-56 miles)

Lodging: Piccolo Hotel La Valle
Day 6: Bicycle to Montalcino
Highlights: Visit the town famous for its red wine, Brunello di Montalcino, Abbey of San'Antimo, wine tasting
This morning we'll start pedaling among the bare clay hills of the Chianti Senese dotted with Italian cypresses and poderi the typical ancient Tuscan farms. The quaint village square in Trequanda is an excellent mid-morning cappuccino stop. As we continue down the Asso Valley, we'll leave the clay hills and ride through vineyards as we make our way to the Etruscan village and wine town of Montalcino. This fortified town was used as a shelter by Sienese nobles during the 16th century, but is more famous today for producing one of Italy's premier red wines, Brunello di Montalcino. You can rest in one of the many wine bars or continue pedaling on a scenic route to the famous Abbey of Sant'Antimo for a visit of this spiritual retreat. We'll have a special wine tasting together late this afternoon so no matter which activity you choose be sure to be back to enjoy this treat. Dinner is on your own tonight. Daily distance: 52-75 km, (32 -47 miles)

Lodging: Hotel dei Capitani and Vecchia Oliviera Hotel
Day 7: Bicycle from Montalcino to Siena
Highlights: Convents and fortified towns dot the landscape, Siena.
The full beauty of the Tuscan landscape, lush green fields and forests of the Orcia Valley and the barren eroded clay hills of Central Tuscany all unfold before us today as we leave Montalcino and pedal to Siena. Shepherds keep watch over their flocks and cypress trees punctuate the horizon. Siena is Italy's best-preserved medieval city and rivaled Florence for dominance in Tuscany during the 1300s. You'll be transported back in time as soon as you enter the city walls. We'll have dinner together this evening. Daily Distance: 60kms (37 miles)

Lodging: Hotel Santa Caterina
Day 8: Rest day in Siena
Highlights: Medieval town of Siena, Piazza del Campo, guided visit
We'll have a guided tour of the city this morning and learn about the Palio, the horse race that takes place twice a year in the main square. Take the afternoon to explore on your own. We'll suggest the best places for lunch, gelato and for dinner on your own this evening. No bicycling today.

Lodging: Hotel Santa Caterina
Day 9: Siena to Greve in Chianti
Highlights: Castellina in Chianti, wine tasting at the famous Macelleria Falorni
We'll leave Siena and climb some of the famous Chianti hills as we make our way to Greve, the cultural capital of the region. You'll notice the difference in landscapes today as you ride through steep-sided forested valleys. Vineyards and perfectly-restored, country-houses add variety. We'll enjoy a wine tasting and sample some local, cured-meat specialties at the famous Macelleria Falorni, before dinner together tonight. Daily distance: 50-60 km (31-37 miles)

Lodging: Albergo da Verrazzano
Day 10: Bicycle from Greve in Chianti to Florence
Highlights: Renaissance Florence
It's a fairly short ride to the outskirts of Florence where we'll regroup and ride into town together. The afternoon is yours to explore this capital of Renaissance Italy. Our hotel in Florence lies on the banks of the Arno River, close to the Uffizi Gallery. We'll enjoy a farewell dinner together this evening. Daily distance: 30 km (19 miles)

Lodging: Hotel Balestri
Day 11: Tour ends in Florence, Italy
Highlights: Florence
After breakfast in the hotel, you're ready to become a tourist again. You're on your own now, so get out there and visit Michelangelo's David at the Accademia, Botticelli's Birth of Venus and the other masterpieces of the Uffizi Gallery, and more. Have a great trip!

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