Bicycling the Best of Southern Tuscany

  • Itinerary Summary

    Bicycle through the heart of Tuscany on a tour that begins in Cortona made famous by Frances Mayes in her book, "Under the Tuscan Sun." From Cortona you pedal to the beautiful Val d'Orcia recognized by UNESCO as a "World Heritage Landscape" for its unique blend of human and natural environments. Over the course of eight days you'll visit Pienza, Montepulciano, Montalcino, and Siena. Prepare to explore the picture postcard landscape of Tuscany, one of the most beautiful regions in Italy.

    ***If this sounds great but you prefer a longer tour check out our Bicycling the Best of Southern Tuscany Plus! Florence tour.***

    View Day-by-Day Itinerary
    Hide Day-by-Day Itinerary
    1. Day 1: Arrive today in Cortona

      Highlights: Ancient Etruscan city of Cortona, Etruscan Museum, setting for Frances Mayes book "Under the Tuscan Sun"

      You are in the spectacular hill town of Cortona today looking over the Chiana River valley (the "Val di Chiana"). Cortona offers the perfect introduction to Tuscany since its founding as an Etruscan town dates to 600 BC. Today Cortona retains the look and character of a Medieval city. Come a day early to see the newly restored Etruscan Museum or the Diocesan Museum with its Fra Angelico paintings. We'll fit bikes late this afternoon before going to dinner together.

      Distance: Test Ride. Meals: D

      Lodging: Relais Villa Marsili

    2. Day 2: Bicycle from Cortona to San Casciano dei Bagni

      Highlights: Views across the Val di Chiana, Lake Trasimeno, and the spa town of San Casciano dei Bagni

      You'll pedal south today across the Chiana Valley to the spa town of San Casciano dei Bagni. San Casciano sits on the slopes of Monte Cetona, the northernmost of a series of extinct volcanoes in central Italy. Enjoy views looking back on your route from Cortona across the Val di Chiana. Enjoy a dip on the thermal pool overlooking the valley before dinner together.

      Distance: 75km (47 miles). Meals: B, D

      Lodging: Hotel Fonteverde

    3. Day 3: Bicycle the Orcia Valley - "Val d'Orcia" to Pienza

      Highlights: Pienza and the Val d'Orcia, Tuscany

      You'll ride through Radicofani today dominated by its 11th century castle and continue through the Orcia Valley to Pienza, home of Pope Pius II. Pope Pius turned this tiny village into a showpiece of Renaissance town planning in the 16th century. Our hotel tonight is just inside the city walls. Take a walk around Pienza and sample the local wines and cheeses (we highly recommend the Pecorino that is wrapped in chestnut leaves and aged under a bed of ashes allowing for uniform drying and aging).

      Distance: 60km (37 miles). Meals: B, D

      Lodging: Hotel Relais il Chiostro di Pienza or Hotel Residence Casanova

    4. Day 4: Cycle Pienza to Montepulciano and the Val d'Orcia.

      Highlights: Wine village of Montepulciano, Bagno Vignoni thermal springs and San Quirico d'Orcia

      Your loop ride today takes you through the wine village of Montepulciano and into the heart of the Orcia Valley. This valley is unique in Tuscany. Composed of poor clay soils the 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. The margins of the valley are lined with volcanic plateaus allowing for better soils to cultivate grapes and olives. Cycle through the tiny Medieval spa of Bagno Vignoni and on to San Quirico d'Orcia.

      Distance: 55km (34 miles). Meals: B, D

      Lodging: Hotel Relais il Chiostro di Pienza or Hotel Residence Casanova

    5. Day 5: Bicycle from Pienza to the wine town of Montalcino

      Highlights: Brunello di Montalcino, wine tasting, optional loop to the Abbey of San'Antimo

      This morning starts with a ride on the ridgeline of the bare clay hills north of Pienza. Cypress trees mark the entrances to isolated Tuscan farms on distant hills. The quaint village square in Trequanda is an excellent mid-morning cappuccino stop. As you continue down the Asso River Valley, you leave the clay hills and ride through vineyards as you make our way to the Etruscan village and wine town of Montalcino. This fortified town sheltered summering Sienese nobles during the 16th century, but today is more famous for producing one of Italy's premier red wines, Brunello di Montalcino. Call it a day and head to the hotel or take an extra ride to the famous Abbey of Sant'Antimo. We have a special wine tasting planned this evening.

      Distance: 59-79km (37-49 miles). Meals: B

      Lodging: Hotel dei Capitani

    6. Day 6: Bicycle from Montalcino to Siena

      Highlights: Monte Oliveto Maggiore, the "Crete Senesi," Siena

      The full beauty of the Tuscan landscape with the lush green fields and forests of the Orcia Valley and the barren clay hills of Central Tuscany unfold before us today as you leave Montalcino and pedal to Siena. You'll pass by the historic monastery of Monte Oliveto Maggiore and spin along the eroded chalk hills of the Crete Senesi. Siena remains Italy's best-preserved medieval city and rivaled Florence for dominance over Tuscany during the 1300s. You'll be transported back in time as soon as you enter the city walls. We'll take a guided tour of the city later this afternoon and learn about the Palio, the horse race that takes place twice a year in the main square.

      Distance: 57km (35 miles). Meals: B

      Lodging: Hotel Santa Caterina

    7. Day 7: Rest day in Siena

      Highlights: Siena, ride to Castello di Brolio

      You have the option today to take a rest from the bike and enjoy some sightseeing in Siena or join us on a loop ride into the Chianti hills. Not far from Siena is the famous Castle of Brolio or, "il Castello di Brolio." Brolio is the estate where the blend of wines that today make up Chianti was invented. This famous Tuscan wine is a blend of 70% Sangiovese, 20% Canaiolo and 10% Malvasia or Trebbiano wines. We'll be back to Siena in time for you to enjoy gelato or an aperitivo on your own in Piazza del Campo, before dinner together.

      Distance: Optional Ride 48km (30 miles). Meals: B, D.

      Lodging: Hotel Santa Caterina

    8. Day 8: Cycling tour ends in Siena

      Highlights: Siena

      Enjoy more of this fabulous city, or head to Florence or Rome.

    • Highlights

      Cortona, Siena, Montalcino, UNESCO World Heritage Landscapes in Val d'Orcia
    • Includes

      Use of a quality 27-30 speed bicycle; 8 days, 7 nights' accommodation; all breakfasts, 5 dinners with wine; wine tasting; guided tour of Siena plus "The Usual"
    • Countries

    • Begin/End

      Cortona / Siena
    • Arrive/Depart

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

      306-374km (189-231 miles)
    • Daily Distance

      Average per day if you ride every mile 62km (38 miles)
    • Rating

      301 Expect hilly terrain with short climbs (2-3 miles) and at least one extended climb of 6-7 miles each day.
    • Terms

      Terms & Conditions
  • Dates Price Private Room Charge Notes
    Sep 3-10, 2017 USD$3850 US$550 Guaranteed to Go! Book it
    Jun 17-24, 2018 USD$3850 USD$550 Book by November 10th and Save $200 per person. Book it
    Aug 19-26, 2018 USD$3850 USD$550 Book by November 10th and Save $200 per person. Book it
    Sep 16-23, 2018 USD$3850 USD$550 Book by November 10th and Save $200 per person. 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 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

    • Wonderful scenery and incredibly charming towns. The food was among the best I''ve ever had. The best vacations of my life!

      Jack I., Boulder, CO
    • Awesome!!! This truly exceeded our (my wife and myself as well) expectations. Great team! Wonderful, unforgettable experiences! A fantastic way to explore other countries and cultures!

      Frank G., Fairport, NY
    • Everything was incredible! As my first experience traveling abroad, I am now spoiled towards any other travel! Guides were very knowledgeable on a variety of topics; bikes were awesome and perfectly fitted for each person; and the food!!!!!

      Tracey G., Fariport, NY

Find a Tour:

Explore Map