Bicycling the Best of Southern Tuscany Plus! Florence

Bicycling the Best of Southern Tuscany Plus! Florence

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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Tour Style: Classic Hold A Space Request Private Departure Download Itinerary Tour Map
  • Trip At-A-Glance
  • Tour Summary
  • Daily Itinerary
  • Travel Information
  • Map
  • Reviews
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Trip At-A-Glance

Trip At-A-Glance

  • Length / 12 Days
  • Total Distance / 545-613km (336-378 miles)
  • Avg. Distance / 68km (42 miles) per riding day
  • Tour Level & Tour Style / 3.5 Classic
  • Countries / Italy
  • Begin/End / Cortona / Shuttle to Florence S.M. Novella Train Station
  • Price / From USD$4950
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Tour Summary

Tour Summary

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

    Keep in Mind: We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

    This tour is our most popular cycling tour of Tuscany. Book early to guarantee your spot.
  • Includes
    12 days, 11 nights' accommodation; all breakfasts, 7 dinners with wine; 2 wine tasting; guided tour of Siena; shuttle to Florence train station; and the usual (see below).

    Learn more about what is included and what to expect on your Classic tour at the Classic Tour Style page.
  • Arrive / Depart
    Rome Fiumicino Airport (FCO) or Florence Airport (FLR) / Florence
  • Overall Tour Level
    3.5 difficulty level 3.5
  • Daily Ride Summary




    Day Level


    Test ride
    75km / 1127m
    Very hilly
    difficulty level 4.5
    59km / 1026m
    Very hilly
    difficulty level 4.0
    55km / 859m
    Rolling hills
    difficulty level 3.0
    79km / 1426m
    Very hilly
    difficulty level 5.0
    57km / 941m
    Rolling hills
    difficulty level 3.0
    48km / 896m
    difficulty level 3.5
    68km / 1104m
    Very hilly
    difficulty level 4.0
    62km / 1306m
    difficulty level 4.0
    Today's ride is an optional loop ride
    49km / 842m
    difficulty level 3.0
    44km / 1015m
    Very hilly
    difficulty level 3.5
    Today's ride is an optional loop ride
    Last day

Terrain Legend

Gentle Gentle

Rolling hills Rolling hills

Hilly Hilly

Very hilly Very hilly

Mountainous Mountainous

Daily Itinerary
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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 and do a test ride late this afternoon before going to dinner together.

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 (47mi)
  • Gain: 1127m (3697ft)
  • Terrain: Very hilly
  • Day Level: difficulty level 4.5
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 3: Bicycle the Orcia Valley - "Val d'Orcia" to San Quirico

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).

DAY 4: Cycle San Quirico 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.

DAY 5: Bicycle from San Quirico to the wine town of Montalcino

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

This morning starts with a ride on the ridgeline of the bare clay hills north of San Quirico. 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 aperitif planned this evening.

  • Distance: 79km (49mi)
  • Gain: 1426m (4677ft)
  • Terrain: Very hilly
  • Day Level: difficulty level 5.0
  • Meals: Breakfast
  • Lodging:

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 (36mi)
  • Gain: 941m (3086ft)
  • Terrain: Rolling hills
  • Day Level: difficulty level 3.0
  • Meals: Breakfast
  • Lodging:

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: 48km (30mi)
  • Gain: 896m (2939ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.5
  • Meals: Breakfast, Dinner
  • Lodging:

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.

  • Distance: 68km (42mi)
  • Gain: 1104m (3621ft)
  • Terrain: Very hilly
  • Day Level: difficulty level 4.0
  • Meals: Breakfast, Dinner
  • Lodging:

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 (39mi)
  • Gain: 1306m (4284ft)
  • Terrain: Hilly
  • Day Level: difficulty level 4.0
  • Meals: Breakfast
  • Lodging:

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 together.

  • Distance: 49km (31mi)
  • Gain: 842m (2762ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.0
  • Meals: Breakfast
  • Lodging:

DAY 11: Loop ride in the Chianti Wine Region

Highlights: Gaiole, the Chianti Hills, Radda in Chianti

Your last day of cycling in the Chianti hills is a loop packed with enchanting sights. Every turn rewards you with stunning vistas over immaculate Chianti vineyards, olive groves, and dense forests. It's a short ride so take your time and explore the picturesque little villages and hamlets like Gaiole, Vertine, and Lecchi. Experience medieval life at the Spaltenna Castle and the Coltibuono Abbey. Or simply take it easy discovering every nook and cranny of charming Radda in Chianti. We’ll enjoy a celebratory dinner together this evening.

  • Distance: 44km (28mi)
  • Gain: 1015m (3329ft)
  • Terrain: Very hilly
  • Day Level: difficulty level 3.5
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 12: We'll transfer you to the train station in Florence

Highlights: Florence

After breakfast we'll shuttle you to Florence's S.M. Novella train station in the center of town (arrival by around 11 a.m.), and from there you can take a taxi or use public transportation to continue your exploration of Italy. First on the list should be a visit Michelangelo's David at the Accademia, Botticelli's Birth of Venus and the other masterpieces of the Uffizi Gallery. Make sure to book your museum visits in advance.

  • Meals: Breakfast
Travel Information

Travel Information

Day 1: Arrival Information

Arrive today in Cortona

Meeting time 2 p.m. - on Day 1, meet your fellow cyclists and Tour Leaders at the Day 1 Hotel specified on the itinerary.


As you are planning, remember that the hotels listed in our itineraries are our primary hotels and are - in rare cases - subject to change. Before you make arrangements, check with us if your tour departure is guaranteed. If your tour departure is out further than 6 months, please also check with us as there might be slight changes to the itinerary.

The below information will help you plan your arrival. For more tips or other routes, you might like Rome2Rio. The fare and timing information listed below is approximate.

The closest airports are Florence (FLR) and Pisa (PSA). Rome (FCO) is a 2-3-hour train ride away.

Flying into Florence and continuing to Cortona:

  1. Vola in Bus shuttle to the Firenze S.M. Novella train station (20 min/EUR 6) or taxi to the train station (15-20 min/fixed rates EUR 20 (weekdays), EUR 23 (weekend), luggage EUR 1/piece)
  2. Train to Camucia-Cortona (1.5 hours/fares vary)
  3. Taxi from Cortona train station to Day 1 Hotel (5 min/EUR 15)

Look up Italian train schedules at or Questions? See our information on taking trains in Europe here or ask us.

Day 12: Departure Information

We'll transfer you to the train station in Florence

Your trip ends on the final day with a complimentary shuttle drop-off at the Florence Santa Maria Novella Train station, arriving at around 11:00 a.m. (takes about 1.5 hours). Your spot on the shuttle is already reserved.

The below information will help you plan your departure. For more tips or other routes, you might like Rome2Rio

Flying out of Florence:

  • Vola in Bus shuttle from the S.M.N. Florence train station to the Florence Airport (20 min/EUR 6)
  • or taxi (15-20 min/fixed rates EUR 20 (weekdays), EUR 23 (weekend), luggage EUR 1/piece)

Keep in Mind

We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

This tour is our most popular cycling tour of Tuscany. Book early to guarantee your spot.

Pre-Trip Planning Checklist

To Do Today!

6 to 3 Months Prior to Tour Start Date

  • Check the online itinerary of your trip and review the arrival and departure information under the "Travel Information" tab to see meeting place and time, if a reservation on a complimentary ExperiencePlus! Shuttle (if applicable) is required, and other important information to help you plan your arrival and departure.
  • Reserve your flights after you know you have a confirmed tour departure. Please check with our office if you do not know if your trip is confirmed.
  • Book your pre and post-tour hotel nights.
  • Begin your chosen training program.
  • Final payment is due 90 days (120 days for Bike &Barge/Boat tours) prior to the tour start. Please refer to your Invoice and the Final Payment Reminder e-mail you have received for detailed instructions.

6 to 2 Weeks Prior to Tour Start Date

  • Start reading one of the books or watching one of the movies from our Reading and Movie Lists:
  • Plan what you are going to pack and start packing! Refer to the Packing Lists on our website at
  • We'll email you your access code to Digital Daysheets, Hotel Itinerary, Participant Roster, names and contact information of your Tour Leaders, emergency phone numbers, and other important departure information about 2 weeks prior to your tour start date. All this will be provided to you via a feature called Experiences via the RideWithGPS App (tracks available but not necessary for navigation on Classic, Expedition, Spotlight and Bike & Boat tours).

Day of Your Flight

Get as much sleep on the plane as you can. Pack your Getting To and Away information and one day of cycling gear in your carry-on. See you soon!

What to Expect on Tour

Classic Tour Style

Learn more about what is included and what to expect on your Classic tour at the Classic page.





  • Sailing the boat, every afternoon relaxing on the boat after biking and swimming, lovely dinners, hearty breakfasts, bee keepers, traditional dinner out, rides through the islands (up and down!), guides, fellow passengers, crew on the boat-- really it was ALL great.

    Cheryl A., Colchester, VT - June 2021
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