Bicycling the Best of Southern Tuscany Plus! Florence

  • 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 twelve days you'll visit Pienza, Siena, San Gimignano and Radda in Chianti on your way to Florence. 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 shorter tour check out our Bicycling the Best of Southern Tuscany tour.***

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    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, alternative ride to Castello de 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: Bicycle from Siena to the famous medieval town of San Gimignano

      Highlights: San Gimignano, the town of towers

      Your bike ride today takes you into the heart of Tuscany. You will pedal past vineyards, 17th century villas, and small towns on our way to San Gimignano, one of the best-preserved medieval villages in Italy and designated a UNESCO World Heritage Site. San Gimignano is famous for its many towers, remnants of the 13th and 14th centuries (there was once more than 100 in the village). We'll have dinner tonight at one of our favorite restaurants.

      Daily Distance: 68km (42 miles). Meals: B, D

      Lodging: Hotel Relais Santa Chiara

    9. Day 9: Loop ride to Volterra

      Highlights: Bicycling to Etruscan town of Volterra

      You'll be San Gimignano again tonight and we've planned a loop ride to Volterra, one of most important Etruscan towns in Italy. Those who wish can continue pedaling to explore the rugged hills of southern Tuscany while the rest of us go to Volterra for some sightseeing. Ancient history fans will want to visit the Etruscan museum and both the Etruscan and Roman ruins on your own this afternoon.

      Distance: 62km (39 miles). Meals: B

      Lodging: Hotel Relais Santa Chiara

    10. Day 10: Bicycle from San Gimignano to Radda in Chianti

      Highlights: Castellina in Chianti, wine tasting, the Chianti wine region

      Your ride today takes you into the heart of Tuscany's famous Chianti region. You'll be in Radda in Chianti this evening and on the way there we will stop for a stroll in Castellina in Chianti. Radda is a gem of a small town and historically it was an important junction for traveler's heading north and south from Florence to Siena. We'll enjoy a wine tasting before dinner together.

      Distance: 49km (30 miles). Meals: B, D

      Lodging: Palazzo San Niccolò

    11. Day 11: Look for Itinerary changes in 2018 - Bicycle through the Chianti Wine Region to Florence

      Highlights: Renaissance Florence, the Chianti Hills, Greve in Chianti

      Today is the last ride of your cycling tour of Tuscany so be sure to enjoy the sights on your way to Florence. Stop in Greve in Chianti to visit the main square and the famous Macelleria Falorni, producer of local salumi. The afternoon is yours to explore Florence, the capital of Renaissance Italy. Our hotel in Florence lies on the banks of the Arno River, close to the Uffizi Gallery. We'll enjoy a celebratory dinner together this evening.

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

      Lodging: Hotel Plaza Lucchesi.

    12. Day 12: Cycling tour ends in Florence. We'll shuttle you to Florence in 2018

      Highlights: Florence

      After breakfast in the hotel, you're ready to become a "regular" tourist again - get out there and visit Michelangelo's David at the Accademia, Botticelli's Birth of Venus and the other masterpieces of the Uffizi Gallery. Enjoy all this wonderful city has to offer.

      Meals: B

    • Highlights

      Siena, Cortona, Montalcino, Chianti wine region, UNESCO World Heritage Landscapes in Val d'Orcia, San Gimignano, Florence
    • Includes

      Use of a quality 27-30 speed bicycle; 12 days, 11 nights' accommodation; all breakfasts, 8 dinners with wine; 2 wine tastings; guided tour of Siena plus "The Usual"
    • Countries

    • Begin/End

      Cortona / Florence
    • Arrive/Depart

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

      545-613km (336-378 miles)
    • Daily Distance

      Average per day if you ride every mile 68km (42 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 3-14, 2017 USD$4950 USD$650 Guaranteed to Go! Book it
    Jun 17-28, 2018 USD$4950 USD$650 Book by November 10th and Save $200 per person. Book it
    Aug 19-30, 2018 USD$4950 USD$650 Book by November 10th and Save $200 per person. Book it
    Sep 16-27, 2018 USD$4950 USD$650 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

    • Beautiful scenery, with just the right amount of challenge, fantastic food and wine!

      Sara L., New Castle, NH
    • The cycling event of my lifetime!! It was awesome! Fabulous! Outstanding!

      Kay E., Seattle, WA
    • The perfect balance of cycling, sightseeing, exploring and dinning. It was amazing.

      Barbara P., Lafayette, CA

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