Cycling through the history of the red wine. History, enogastronomy, art, nature and joy of life, all together in a wonderful bike trip from Siena to Florence. Between these two pearls of world heritage, here stretches the the Chianti Classico territory: the quintessential Tuscany, an area blessed by a peaceful countryside and charming villages, producing one of the best wine worldwide by 2500 years. We’ll feel we are cycling inside a renaissance painting!
Nobile di Montepulciano e Chianti wines
The strong and alive traditions in Siena
The Crete Senesi landscape
Elisa's delicious kitchen at Il Molinello
|1||Benvenuti in Toscana!||Warm up ride||D|
|2||Montepulciano loop tour||Cycling 70Km/1200m||B D|
|3||From Asciano to Siena||Cycling 40Km/750m||B|
|4||From Siena to San Casciano Val di Pesa||Cycling 50Km/800m||B D|
|5||San Gimignano loop tour||Cycling 60Km/600m||B D|
|6||From San Casciano Val di Pesa to Florence||Departure||B|
We suggest to arrive at Florence airport, according to your needs we’ll shuttle you or we’ll meet directly at our first hotel in Siena. After a mandatory toast with a local wine we properly introduce the whole tour and we make a careful bike fitting, then you’ll be ready for your warm up ride to the pretty medieval town of Serre di Rapolano, a perfect start for the upcoming adventure. Elisa and Andrea will host us for the first two nights, let us tasting their great extra virgin olive oil.Overnight: Asciano
Your first ride is a beautiful loop through the Val d’Orcia, a quintessential tuscan landscape, made out of rolling hills dotted with cypress trees, its landscape is listed as a UNESCO World Heritage Site. The scenery changes from dry and brown in fall and winter, to emerald green and blossoming in spring, to the amazing golden fields in summer. We’ll pass through the stunning village of Montepulciano where a stop is mandatory to taste one of the best Italian wines: the Vino Nobile di Montepulciano docg.Overnight: Asciano
Today you leave the peaceful olive grove of Elisa and Andrea in the direction of Siena. The ride will cross the splendid Crete Senesi, the typical Tuscan countryside, among rural village, rolling hills covered with olive groves and cypress hedges, plowed fields and small churches. You’ll have even the chance to enjoy some Strade Bianche (gravel roads), home of the popular cycling event Eroica, the legendary race that every October brings thousands of enthusiasts to pedal through the lands of this wonderful region. The day ends within the ancient walls of the wonderful city of Siena, a jewel of late medieval architecture.Overnight: Siena
We leave Siena worldwide famous for the fascinating "Contrade" (districts) and for its Palio, a medieval horse race taking place twice a year in the Piazza del Campo square. We suggest to take some energetic Panforte with you, the typical Siena spice cake, made out of nuts and candy fruit, perfect for bike riding!
The ride is across the heart of Chianti Classico, you can stop for rest in the pretty Castellina in Chianti, part of the original “Lega del Chianti” with Gaiole and Radda. The Lega, was a military organization created by Florence in 1384 to protect the whole area. From the original Lega del Chianti was born the Chianti wine protected area, still using the black rooster as a symbol. Then we’ll enter the Val di Pesa, considered the Florence wine area, a place internationally famous thanks to its wine, there we’ll stay in a wine resort, having a great wine tasting.Overnight: San Casciano Val di Pesa
You are riding along the old pilgrimage route called the Via Francigena, where pilgrims and noblemen once traveled north to south through Europe to get in Rome. A quick overview of the history and village plan of San Gimignano (the town of the towers) followed by some free time to visit the amazing churches, ancient walls, boutiques and art galleries, before to take the way back to our countryside hotel.
Let’s discover the typical landscapes of the Chianti Classico area, sinuosus roads going across huge vineyards and pretty villages. We are riding along the old pilgrimage route called the Via Francigena, where pilgrims and noblemen once traveled north to south through Europe to get in Rome. A quick overview of the history and village plan of San Gimignano (the town of the towers) followed by some free time to visit the amazing churches, ancient walls, boutiques and art galleries, before to take the way back to our countryside hotel.Overnight: San Casciano Val di Pesa
Prepare for entering one of the most shining world heritage jewels by bike, such a great experience!
We start among vineyards and olive grows, along the route we’ll see the landscape gradually change into the peaceful the landscape changes gradually, from vineyards and olive groves to a lovely detached houses on the hills that dominate the city.
In the late afternoon we’ll go downtown for a nice walk before of a fantastic dinner in the Renaissance capital, celebrating the Chianti Classico wine, of course!Overnight: Firenze
You can bring your own bike or rent one from us, we offer great bikes from selected Italian and international brands: road bikes, leisure cycling, mountain bikes, e-bikes, all in perfect working conditions. We'll find the best solution for you during the tour customization.
These itineraries are original tours created for real guests, so you may want something different specifically designed to suit your own wishes.
The price of every tour is available upon requests, and varies by time of year, number of guests and level of guiding.
Start dreaming looking through it, then contact us and let's talk. We'll listen to your needs, we'll suggest ideas and propose experiences, and together we'll create your perfect voyage.
Check our Ready to Book section with active and cycle tours in our Mediterranean destinations.