ExperiencePlus! - Bicycle Tours since 1972

Fall Cycling in Tuscany and Umbria

  • Itinerary Summary

    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!
    View Day-by-Day Itinerary
    Hide Day-by-Day Itinerary
    1. Day 1: Arrive in Assisi, Umbria

      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.

    2. 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).

    3. Day 3: Deruta

      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).

    4. 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).

    5. Day 5: Pienza and the Abbey of Monte Oliveto Maggiore

      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).

    6. Day 6: Montalcino and 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).

    7. Day 7: Bike to Siena, Italy

      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).

    8. Day 8: Farewell

      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 plus "The Usual"
    • 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)
    • Rating

      301-401
    • Terms

      Terms & Conditions
  • Dates Price Single Supplement Notes

    * We are happy to match solo travelers who would like to share a room with someone of the same gender. If no match exists, due to hotel pricing, we will charge 50% of the single supplement rate. This fee will be collected at the time of the final payment. If a roommate assignment is available this fee will be refunded at the conclusion of the tour.

  • Stories

    • 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

Find a Tour:

Loading
Or
Explore Map