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Experience Plus - Bicycle Tours since 1972
Cycling the Best of Southern Tuscany
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Bicycle Tours in Italy: Cycling the Best of Southern Tuscany

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.

Day 1: Meet in Torgiano, Umbria

Highlights: Fit bicycles loop ride to Deruta

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 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. 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 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

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: 52 km (32 miles).

Lodging: September 2014 we'll be at Chiostro di Pienza. Otherwise Piccolo Hotel La Valle

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!

Lodging: September 2014 we'll be at Chiostro di Pienza. Otherwise 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 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. 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: 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.

  • Highlights
    Assisi, Ceramics in Deruta, Val d'Orcia, recognized by UNESCO as a "World Heritage Landscape", Cortona, Guided tour of Siena
  • Includes
    "The Usual" plus... Use of a quality 27-30 speed bicycle; 8 days, 7 nights accommodation; 5 dinners, 1 lunch, all breakfasts; wine tasting; guided tour of Siena & Assisi
  • Countries
    Italy
  • Begin/End
    Torgiano / Siena
  • Arrive/Depart
    Rome Fiumicino Airport (FCO) or Florence Airport (FLR)
  • Total Distance
    212 - 248 miles (344 - 402 km)
  • Daily Distance
    Average daily mileage 30 - 35 miles (49 - 57 km)
  • What to Expect
    Medieval & Renaissance cities and villages, vineyards, spectacular scenery and intriguing historical towns
  • 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.
  • Notes
    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.
  • Terms
Dates Price Single
Supplement*
Notes Next
Step
Sep 10 - 17, 2014 $3650 $550 Confirmed. Book It
*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.
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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)
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