Cycling the Best of Southern Tuscany

  • Itinerary Summary

    Join us on a bike tour through Italy that combines the best of Umbria and Southern Tuscany. The bicycle tour includes 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 finish our trip in Siena, Italy's best preserved medieval city.

    If this sounds great but you'd like a longer tour, check out our Cycling the Best of Southern Tuscany Plus! Florence tour, which extends this itinerary by 3 days.

    View Day-by-Day Itinerary
    Hide Day-by-Day Itinerary
    1. Day 1: Meet in Perugia - shuttle to the starting hotel

      Highlights: Shuttle to Torgiano, fit bicycles, loop ride to Deruta

      We offer a complimentary shuttle from Perugia to the tour start in Torgiano. Perugia is the capital of the Umbria region, and is also the European capital of chocolate! It is definitely worth arriving a day, or two early, to explore this wonderful city before your bike trip. Your cycling will begin from 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: 15 km (9 miles). Meals: D

      Lodging: Hotel Al Grappolo d'Oro

    2. Day 2: Loop bicycle ride to Assisi

      Highlights: Bicycle to Assisi, guided visit of Assisi, Roman town of Spello

      Our 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 then 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.

      Daily Mileage: 64 km (40 miles). Meals: B.

      Lodging: Hotel Al Grappolo d'Oro

    3. Day 3: Bicycle to Cortona

      Highlights: Etruscan city of Cortona, Etruscan Museum, Lake Trasimeno, scenic Tuscan countryside

      We will leave Umbria today and enter Tuscany, cycling through the picturesque landscapes that have made Tuscany famous. We'll pedal 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.

      Daily Mileage: 74 km (46 miles). Meals: B, D

      Lodging: Hotel San Michele

    4. 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).

      Daily Mileage: 52 km (32 miles). Meals: B, D

      Lodging: Chiostro di Pienza.

    5. Day 5: Loop ride across Val d'Orcia

      Highlights: The World Heritage Landscape of Val d'Orcia, Bagno Vignoni 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: 30-52 km (18-32 miles). Meals: B

      Lodging: Chiostro di Pienza.

    6. 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 you'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.

      Daily distance: 53-73 km, (33-45 miles). Meals: B, D

      Lodging: Hotel dei Capitani

    7. 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.

      Daily Distance: 58 km (36 miles). Meals: B, D

      Lodging: Chiostro del Carmine

    8. Day 8: Tour ends in Siena

      Highlights: Guided tour of Siena

      We'll offer a guided tour of Siena this morning from 9:00AM to noon. If you'd like to join us please make your departure plans accordingly. In any case thanks for joining us, buon viaggio! If this sounds great but you'd like a longer tour, check out our Cycling the Best of Southern Tuscany Plus! Florence tour, which extends this itinerary by 3 days.

      Meals: B

    • Highlights

      Assisi, Ceramics in Deruta, Val d'Orcia, recognized by UNESCO as a "World Heritage Landscape", Cortona, Guided tour of Siena
    • Includes

      8 days, 7 nights accommodation; 5 dinners, 1 picnic lunch, all breakfasts; wine tasting; guided tour of Siena & Assisi plus "The Usual"
    • Countries

    • Begin/End

      Torgiano / Siena
    • Arrive/Depart

      Rome Fiumicino Airport (FCO) or Florence Airport (FLR)
    • Total Distance

      346 - 388 km (214 - 240 miles)
    • Daily Distance

      Average daily mileage 49 - 55 km (30 - 34 miles)
    • Rating

      201-301 Relatively flat the first 4 days with one climb a day. It gets hillier with multiple climbs each day in the second part. Two rest day options.
    • Terms

      Terms & Conditions
  • Dates Price Private Room Charge 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 private room charge. This charge will be collected at the time of the final payment. If a roommate assignment is available it will be refunded at the conclusion of the tour.

  • Stories

    • After hearing such glowing comments from your previous guests at the last two years'' demo rides here in Ft Collins I had very high expectations and your entire team exceeded them every step of the way. We are already talking about where we want to go with you on our next EP trip!

      Peter S., Fort Collins, CO
    • The trip was fantastic. The experience amazing. Loved every minute. The guides were the best. The food was indescribably delicious.

      Bonnie A., Seattle, WA
    • The best vacation I have ever had. Great exercise, scenery, learning, food and new friends.

      Peter H., Portland, OR
    • I loved exploring all the old towns. I very much enjoyed the company of the other cyclists. I loved the descents. We had a great holiday. Thank you

      Majan S., Malvern, VI Australia
    • The riding was fabulous, I loved the climbs, some were challenging, but the descents were incredible. I felt like a kid screaming down some of the deserted roads we were on. The new titanium bikes are a great addition. Mine fit perfectly and was so comfortable. I loved being with my friends and meeting new folks on the trip as well. The landscape was gorgeous. Oh yes, the chalking (navigational arrows) is another great part of the trip. I also enjoyed the multi-day stays on this tour, it is nice to not have to pack up every day. Thanks for everything, it was a great tour, we all had a blast!

      Sally L., Boulder, CO
    • Do you have any additional comments on hotels? We were having so much fun, we could of camped!

      Tony M., Petersburg, AK
    • What was your favorite experience on this trip? Experiencing the culture, the villages, the meals that were included, the organised wine tours, and cycling was the best way to see it all! My first tour with ExperiencePlus! and I thoroughly enjoyed the entire time in Tuscany. A wonderful tour thanks!

      Tracey M., VI, Australia

Find a Tour:

Explore Map