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Fall Cycling in Tuscany and Umbria
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Bicycle Tours in Italy: Fall Cycling in Tuscany and Umbria

Fall in Tuscany and Umbria, on your bicycle! What better way to enjoy Italy? Join us for a week of cycling, spectacular scenery and fall weather. We start with three nights in Umbria, then three nights in Southern Tuscany before finishing in Siena. Enjoy daily rides in the Umbrian basin to Assisi, Spello, Bevagna, Montefalco and the famous ceramics town of Deruta. Then we head to the Orcia River valley for three nights, past Lake Trasimeno, to the walled town of San Quirico. We enjoy this quiet corner of Tuscany for three days, pedaling to Sant'Antimo, Pienza, San Quirico, and the Abbey of Monte Oliveto Maggiore. Our last night is in Siena. Complete your trip with an extra night or two in this wonderful Renaissance town!

Day 1: Arrive in Assisi, Umbria

Main square in Assisi.

Highlights: Fit bicycles and take a walk around town

Arrive this afternoon in classic Assisi, home of Saint Francis. We fit bikes this afternoon and suggest a walk around town to become familiar with our new home! We have a welcome dinner together this evening.

Day 2: Assisi, Italy

Highlights: Visit Assisi, bicycle the hills of Umbria

Home to Italy's patron saint, St. Francis, Assisi is a beautiful medieval town built on a hill overlooking the Umbrian basin. Our ride takes us from Assisi through the Umbrian hills to the Roman town of Spello. We loop back to Assisi later this afternoon. Dinner together this evening. Mileage: 36-60 km (23-38 miles).

Day 3: Deruta

Typical food.

Highlights: Famous ceramics of Deruta, scenic rides

We pedal to Deruta this morning to visit some ceramic studios. Deruta is famous throughout Italy for classic Italian ceramics (these patterns will be familiar to you from any number of Italian restaurants in the U.S.). After a stroll around town (maybe some shopping?) enjoy a scenic ride through the hilltop towns of Montefalco and Bevagna on the way back to the Assisi. Dinner is on your own this evening. Daily mileage: 75 km (47 miles).

Day 4: Arrive in Tuscany, Italy

Highlights: Riding near Lake Trasimeno, and San Quirico d'Orcia, Tuscany

We pack our bags and head to Tuscany today! We'll ride along the shores of Lake Trasimeno, famous for Hannibal's defeat of the Roman army after crossing the Alps with elephants! We enter Tuscany as we make our way to our home for the next 3 nights in San Quirico d'Orcia. The Orcia river valley will be the focus for our rides over the next few days' rides. Settle into our hotel and enjoy dinner together tonight. Daily mileage: 138 km with shuttle support for those who wish. (86 miles).

Day 5: Pienza and the Abbey of Monte Oliveto Maggiore

Tuscan hills.

Highlights: Bicycle through rural Tuscany to the Renaissance town of Pienza

We head toward the planned Renaissance town of Pienza today. With the help of a number of prominent architects Pope Pius II turned his small hometown into a piece of art in the 16th century. We'll ride north to other medieval towns on a picturesque loop through the Tuscan hills. Our route takes us past the Abbey of Monte Oliveto Maggiore, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. We are back in San Quirico this evening for dinner on your own. Daily mileage: 58 km (36 miles).

Day 6: Montalcino and Abbey of Sant'Antimo

Abbey of Sant'Antimo.

Highlights: Visit the town famous for its red wine, Brunello di Montalcino

Pedal through vineyards and wheat fields this morning 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 today is more famous for producing one of Italy's premier red wines, Brunello di Montalcino. Our scenic route takes us to the famous Abbey of Sant'Antimo and then on to Bagno Vignoni, a Medieval spa. Daily mileage: 52 km (32.5 miles).

Day 7: Bike to Siena, Italy

Pedalling Tuscan countryside.

Highlights: Fortified towns and convents dot the scenery on the ride toward Siena

The full beauty of the Tuscan landscape, from the lush green fields of the Orcia Valley to the barren, chalk hills of Central Tuscany, unfolds before us today as we leave San Quirico and pedal to Siena. Often described as Italy's best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You have time to take a leisurely stroll through this medieval art city this afternoon before we gather for our final dinner together this evening. Daily Mileage: 58 km (36 miles).

Day 8: Farewell

Piazza del Campo in Siena.

Highlights: Continue exploring Siena or move on to other parts of Italy!

You are on your own today after breakfast. We recommend an extra day or two in Siena if you have the time, or you can catch the train south to Rome or north to Florence.
  • Highlights
    Assisi, Classic landscapes of Umbria and Southern Tuscany, San Quirico d'Orcia, Daily loop rides from our base hotels in Umbria and Tuscany, Ceramics in Deruta, Siena and Abbey of Monte Oliveto Maggiore
  • Includes
    8 days, 7 nights accommodation, 4 dinners with wine, all breakfasts
  • Countries
    Italy
  • Begin/End
    Assisi/Siena
  • Arrive/Depart
    Florence, Bologna or Rome
  • Total Distance
    268 - 283 miles (429 - 453 km)
  • Daily Distance
    22.5 - 86 miles (36 - 138 km)
  • What to Expect
    Hilly terrain with some steep stretches
  • Rating
  • Notes
  • Terms
Please call 1-800-685-4565 or e-mail us for the dates for this tour.

Click on the "pins" for details about each day's highlights.

Map Key

Green pinStart
Yellow pinCity (on route)
Red pinEnd
Other city dotCity (not part of route, provided for reference)
First, I want to say that the biking in Umbria and Tuscany trip was absolutely wonderful! I loved the routes that we did (the hills were challenging, but we all survived) - these parts of Italy are just fabulous; the food was terrific; the hotels were very good; everything was well organized; you planned almost perfect weather; and our guides were really great.
Kathy S.
Palo Alto, CA
[ My favorite experience was ] never thinking about the next stop; just knowing we were in great hands. All the hotels were awesome, beautiful. Restaurants were great. The tour leaders were always one step ahead ... such a great memory ... a perfect team. Cannot say enough...
Nancy B.
Denver, CO
The tour leaders were amazing. They even rescued and/or helped several people from other tours who didn't have the support provided by Experience Plus. I would never use another tour company after seeing how the others left their customers high and dry and without support. [What was your favorite experience?] Very hard to single out. The food was amazing; the guides were the best; the country and the scenery was beyond belief, and our co-riders were really fun. I guess I would say the scenery and the food were my favorites, but it was all good ... it was a great experience and I have already recommended you guys to lots of people!
Linda M.
Monument, CO
You did a great job. Our trips to and from were harried, as usual, but once we were in Experience Plus's capable hands, we had no worries.
Robert H.
Brentwood, TN