Cycling the Best of Southern Tuscany Plus! Florence

  • Itinerary Summary

    Join us on a bike tour through Italy that combines the best of Umbria and Southern Tuscany and ends with a spectacular ride into Florence. This bicycle tour visits 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 ride to Siena before bicycling through the heart of the Chianti wine region where we stay in Radda in Chianti. Join us as we sample some of our favorite wines of Tuscany. Our bicycle rides give us ample time to explore some of the most photographed landscapes in Italy, Tuscany is truly a postcard!

    If this sounds great but you don't have time for the full 11 days, check out our Cycling the Best of Southern Tuscany tour, which features the first 8 days of this itinerary.

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    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 definitely worth arriving a day, or two, early to explore before the 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 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 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 we'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: Rest day in Siena

      Highlights: Medieval town of Siena, Piazza del Campo, guided visit

      We'll have a guided tour of the city this morning and learn about the Palio, the horse race that takes place twice a year in the main square. Take the afternoon to explore on your own.

      No bicycling today. Meals: B

      Lodging: Chiostro del Carmine

    9. Day 9: Siena to Radda in Chianti

      Highlights: The Chianti, wine tasting

      We'll leave Siena and climb some of the famous Chianti hills as we make our way to our final climb to Radda in Chianti our home for the night. You'll notice the difference in landscapes today as you ride through steep-sided forested valleys. Vineyards and perfectly-restored, country-houses add variety. Radda is a delightful gem of a small town and was an important junction for traveler's heading to north and south.

      Daily distance: 42 km (26 miles). Meals: B, wine tasting, D

      Lodging: Hotel Palazzo San Niccoló. September 9th departure will be at Palazzo Leopoldo.

    10. Day 10: Bicycle from Radda in Chianti to Florence

      Highlights: Renaissance Florence

      It's your last ride in Italy so be sure to enjoy the sights on your way to Florence. Stop in Greve in Chianti for a short visit of the main square and the famous Macelleria Falorni, producer of local salumi. The afternoon is yours to explore this 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 farewell dinner together this evening.

      Daily distance: 61 km (38 miles). Meals: B, D

      Lodging: Plaza Hotel Lucchesi

    11. Day 11: Tour ends in Florence, Italy

      Highlights: Florence

      After breakfast in the hotel, you're ready to become a tourist again. You're on your own now, so get out there and visit Michelangelo's David at the Accademia, Botticelli's Birth of Venus and the other masterpieces of the Uffizi Gallery, and more. Have a great trip!

      Meals: B

    • Highlights

      Assisi, Ceramics in Deruta, Siena, Montalcino, Chianti wine region , Cortona, Val d'Orcia, recognized by UNESCO as a "World Heritage Landscape", Florence
    • Includes

      11 days, 10 nights accommodation; 7 dinners with wine, 1 picnic lunch, all breakfasts; 2 wine tastings; guided visits of Assisi and Siena plus "The Usual"
    • Countries

    • Begin/End

      Torgiano / Florence
    • Arrive/Depart

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

      460 - 491 km (284 - 303 miles)
    • Daily Distance

      Average daily 51 - 55 km (31 - 34 miles)
    • Rating

      301 Relatively flat the first 4 days with one climb a day. It gets hillier with multiple climbs each day in the second part of the tour. Three 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

    • How would you describe this tour to a friend? Beautiful, culturally rich, challenging riding, fun, great food and wine.

      Gary F., Ft Collins, CO
    • I could not have dreamed that this experience would be so far above our expectations! The tour leaders thought of every detail, made us laugh, got to know us and helped us become better cyclists and appreciate all things Tuscan. We will always remember the sights, foods and folks we met!

      Michelle G., West Chester, OH
    • Cycling in one of the best riding areas of the world with the ambiance and culture of rural Tuscany. ExperiencePlus! stands out relative to other bike tour companies due to the chalked arrows. The family style dinners, nice hotels and excellent guides ensure you''''ll have a great time. Just wish I had more vacation time to do more bike trips with you.

      Joan B., Calgary, Alberta, Canada
    • We had an excellent time on this bike tour. Each day was a great adventure. The Experience Plus guides were super on our tour and the meals they planned were delightful. We really liked the chalked arrows for guidance. We never got lost! We are looking forward to doing another tour in the future with Experience Plus.

      Cliff M., Knockville, TN
    • What was your favorite experience on this trip? The people, the scenery, Tuscany wine regions were fantastic, the day in Assisi wih the guide, cycling through the small villages, the well-marked routes, having the sag wagon there with water and food after a long climb with a head wind.

      Lois C., Holland Landing, Ont, Canada
    • What was your favorite experience on this trip? There were so many - but as Siena is my favorite city in all of Italy I would say the free day there was unmatched. The tour guide was phenomenal, best we've ever had. We thought we knew a lot about Siena but learned even more! We also loved being up late and sitting on the piazza steps in Cortona, incredibly charming, and hanging out with locals in Pienza. But almost all of it was charming! ExperiencePlus! is the ONLY guided bike tour company we would ever use! We love you guys!

      June W., St Paul, MN
    • I loved the tours of Assisi and Siena--both guides were fantastic. I loved a picnic lunch we had in a small hill-top town, where there was a big truck-farmer's market set up and we could get the best fresh fruit. I liked meeting the other participants, who were all very nice. I liked stopping to pick grapes in a random vineyard one afternoon.

      Sharon S., Eugene, OR
    • 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., Toorak, VI, Australia
    • Do you have any additional comments on hotels? We were having so much fun, we could of camped!

      Tony M., Petersburg, AK
    • 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
    • I loved exploring all the old towns. I very much enjoyed the company of the other cyclists. I loved the descents. My favorite day was Day 9 when I was used to the hills and we had this climb to Castellina with a beautiful view of the valley. We had a great holiday. Thank you

      Majan S., Malvern, VI Australia

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