Bicycling the Best of Southern Tuscany Plus! Florence

Pedal through the beautiful hills of Southern Tuscany with ExperiencePlus! on this guided bike holiday.
  • Length 12 days
  • From USD$4950
  • Style/Level Classic 3.5
  • Countries Italy
  • Begin/End Cortona / Shuttle to Florence S.M. Novella Train Station
See related tours

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.***

Highlights

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

Includes

  • 12 days, 11 nights accommodation

  • all breakfasts, 7 dinners with wine

  • 2 wine tasting

  • guided tour of Siena

  • shuttle to Florence train station

  • All Classic tour inclusions

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.


Date Price Private room fee Note

Download Itinerary

We’ll send you a link to a full day by day tour itinerary that can be downloaded and printed so you can review all the details online and offline. This packet also includes details about what to expect on tour and arrival and departure details.
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  • Total distance 545-613km (336-378 miles)
  • Average daily distance 68km (42 miles)
  • Tour style Classic
  • Tour level 3.5

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.

Meals : Dinner
Lodging : Hotel San Michele , Hotel Villa Marsili

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.

Meals : Breakfast, Dinner
Lodging : Hotel Fonteverde

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).

Meals : Breakfast, Dinner
Lodging : Residence Casanova , Relais Palazzo del Capitano

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.

Meals : Breakfast, Dinner
Lodging : Residence Casanova , Relais Palazzo del Capitano

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.

Meals : Breakfast
Lodging : Hotel dei Capitani

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.

Meals : Breakfast
Lodging : Hotel Santa Caterina

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.

Meals : Breakfast, Dinner
Lodging : Hotel Santa Caterina

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.

Meals : Breakfast, Dinner
Lodging : Hotel Leon Bianco

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.

Meals : Breakfast
Lodging : Hotel Leon Bianco

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.

Meals : Breakfast
Lodging : Palazzo Leopoldo

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.

Meals : Breakfast, Dinner
Lodging : Palazzo Leopoldo

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

Visit our Tour Level page to learn more about terrain levels and how we determine day and tour levels.



Pre-trip planning checklist



  • The perfect balance of cycling, sightseeing, exploring and dinning. It was amazing.

    Barbara P., Lafayette, CA
  • The cycling event of my lifetime!! It was awesome! Fabulous! Outstanding!

    Kay E., Seattle, WA
  • Beautiful scenery, with just the right amount of challenge, fantastic food and wine!

    Sara L., New Castle, NH