Join us on a bike tour through Italy that combines the best of Umbria and Southern Tuscany and ends with a spectacular ride into Florence. This bicycle tour visits Assisi, home to St. Francis and pedals to Deruta, famous for its ceramics, and Cortona, made famous by Frances Mayes in her book, Under the Tuscan Sun. From Cortona we bicycle to Pienza in the beautiful Val d'Orcia, recognized by UNESCO as a "World Heritage Landscape" for its unique blend of human and natural environments. We loop back north and ride to Siena before bicycling through the heart of the Chianti wine region where we stay in Radda in Chianti. Join us as we sample some of our favorite wines of Tuscany. We'll taste some local wines at the famous Macelleria Falorni. Our bicycle rides give us ample time to explore some of the most photographed landscapes in Italy, Tuscany is truly a postcard!
If this sounds great but you don't have time for the full 11 days, check out our Cycling the Best of Southern Tuscany tour, which features the first 8 days of this itinerary.
Day 1: Meet in Torgiano, Umbria
Highlights: Fit bicycles and loop ride to DerutaArrive 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 SpelloOur ride takes us across the Umbrian Basin to the Roman town of Spello with its impressive city gates and original Roman walls. We'll continue 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. We loop back to Torgiano later this afternoon. Dinner is together this evening. Daily Mileage: 62 km (39 miles).
Lodging: Hotel Al Grappolo d'Oro
Day 3: Bicycle to Cortona
Highlights: Etruscan city of Cortona, Etruscan Museum, Lake Trasimeno, scenic Tuscan countrysideWe 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
Day 4: Montepulciano, Val d'Orcia and Pienza
Highlights: Montepulciano, Pienza and Val d'Orcia, TuscanyWe'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: 52 km (32 miles).
Day 5: Loop ride across Val d'Orcia
Highlights: The World Heritage Landscape of Val d'Orcia, Bagno Vignoni thermal springs and historic town centerWide 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: 30-52 km (18-32 miles).
Day 6: Bicycle to Montalcino
Highlights: Visit the town famous for its red wine, Brunello di Montalcino, Abbey of San'Antimo, wine tastingThis 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: 54-75 km, (33-47 miles)
Lodging: Hotel dei Capitani
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: 60 km (37 miles)
Lodging: Hotel Santa Caterina
Day 8: Rest day in Siena
Highlights: Medieval town of Siena, Piazza del Campo, guided visitWe'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 Radda in Chianti
Highlights: The Chianti, wine tastingWe'll leave Siena and climb some of the famous Chianti hills as we make our way to our final climb to Radda in Chianti our home for the night. You'll notice the difference in landscapes today as you ride through steep-sided forested valleys. Vineyards and perfectly-restored, country-houses add variety. Radda is a delightful gem of a small town and was an important junction for traveler's heading to north and south. Daily distance: 56 km (35 miles).
Lodging: Hotel Palazzo San Niccoló
Day 10: Bicycle from Radda in Chianti to Florence
Highlights: Renaissance FlorenceIt's your last ride in Italy so be sure to enjoy the sights on your way to Florence. Stop in Greve in Chianti for a short visit of the main square and the famous Macelleria Falorni, producer of local salumi. 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: 58 km (36 miles)
Lodging: Plaza Hotel Lucchesi
Day 11: Tour ends in Florence, Italy
Highlights: FlorenceAfter 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!
HighlightsAssisi, Ceramics in Deruta, Siena, Montalcino, Chianti wine region , Cortona, Val d'Orcia, recognized by UNESCO as a "World Heritage Landscape", Florence
Includes"The Usual" plus... Use of a quality 27-30 speed bicycle; 11 days, 10 nights accommodation; 7 dinners with wine, all breakfasts; 2 wine tastings; guided visits of Assisi and Siena
Begin/EndTorgiano / Florence
Arrive/DepartRome Fiumicino Airport (FCO) or Florence Airport (FLR) / Florence
Total Distance273 - 322 miles (442 - 522 km)
Daily DistanceAverage daily mileage 30 - 36 miles (49 - 58 km)
What to ExpectMedieval & Renaissance cities and villages, vineyards, spectacular scenery and intriguing historical towns
Relatively flat the first 4 days with one climb a day. It gets hillier with multiple climbs each day in the second part of the tour. Three rest day options.
NotesIf this sounds great but you don't have time for the full 11 days, check out our Cycling the Best of Southern Tuscany tour, which features the first 8 days of this itinerary.