Classic Tuscany Self-Guided

Day to Day

Tour Map

Day 1: Benvenuti in Toscana!

Tour briefing, bike fitting and warm up ride

We suggest you arrive at Florence airport, according to your needs we’ll shuttle you, or we’ll meet directly at our accommodation in San Gimignano city center. San Gimignano is a Unesco heritage site thanks to its many scenic towers and its long history, one of the first independent communes of Italy. After a mandatory toast with a local wine like Vernaccia di San Gimignano, ancient wine with a distinctive character, we'll 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, a perfect start for the upcoming adventure.

Day 2: San Gimignano to Gaiole in Chianti

An Epic day along the Eroica roads

We leave San Gimignano surrounded by pristine Sangiovese vineyards, admiring the distinctive skyline as we move towards the Chianti Classico region. In the past this area was the scene of fierce clashes between the cities of Florence and Siena, disputing over these lands for a long time, in this regard it is interesting the legend of the black rooster, symbol of the region, that we invite you to read. This area today it's a place of wonderful serenity and beauty.
But let's not forget we are also in the realm of the Eroica, the iconic vintage bike ride across the Chianti region, so we will have an exciting taste of the Strade Bianche experience, gravel roads with well-trodden surfaces where it will be fun and romantic to ride. The route winds through the pretty villages and countryside of Castellina in Chianti and Radda in Chianti, up to Gaiole in Chianti, where we will spend the night.

Day 3: Gaiole in Chianti to Asciano

At the origins of Chianti Classico wine

Let's cross the Chianti area, and conquer the Brolio Castle by climbing among cypress trees. This stunning property is probably the most important symbol of the Chianti area. It belongs to the noble Ricasoli family, of which the most illustrious representative was the baron Bettino di Ricasoli, a prominent politician of the just Kingdom of Italy but, above all, a researcher and wine entrepreneur of great foresight. After years of research and experimentation, in 1872 the Baron was finally able to define a method, which became the official formula for the production of Chianti wine. We’ll pedal coasting the fortified walls of the Castle, then we’ll immerse ourselves in the vineyards in the valley. We could have an aperitif at the classy Rapolano Thermal Baths, with great views over the bare Senesi Hills. Elisa and Andrea will host us at their agritourism with pool. Before dinner, let us taste their great extra virgin olive oil.

Day 4: Asciano to Pienza

Across the beautiful villages of Montepulciano and Pienza

Today we ride 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 Montepulciano where a stop is mandatory to taste one of the best Italian wines: the Vino Nobile di Montepulciano docg. We end in the amazing village of Pienza, known as the “ideal city” and considered to be the incarnation of a Renaissance utopia, UNESCO World Heritage Site as well. Here we'll taste some great Pecorino cheeses made by local shepherds settled here a few generations ago from the island of Sardinia.

Day 5: Pienza to Montalcino

In the land of the Brunello di Montalcino wine

We leave the romantic Renaissance atmosphere of Pienza, heading towards the kingdom of Brunello di Montalcino, one of the most renowned and precious wines in the world. The itinerary winds its way through barren fields, woods, olive groves and vineyards, of course, wonderful vineyards planted with Sangiovese grapes, called "Brunello" in this area. After crossing the river Orcia, we meet the majestic Sant’Antimo Romanic abbey, marvelously immersed in the countryside. If you are lucky you could listen to the monks’ Gregorian chant, a really unique experience. The last climb of the day leads us to the village of Montalcino, which in addition to the pride of a great wine can also flaunt a beautiful medieval village.

Day 6: Montalcino to Siena

From the vineyards of Montalcino to the rolling hills of Siena

From the top of the Montalcino hill, we descend along an exciting descent taking us under the medieval walls of the ancient city of Buonconvento. Then we go up through the typical landscapes of the "Crete Senesi", made up of rolling hills, gullies, lonely farmhouses, and small parish churches. Riding along the landscapes you have admired many times in postcards and photos of Tuscany will provide unique emotions.
The day ends right in Siena, a lively but still authentic city. Siena is the most medieval town of Tuscany, divided in "Contrade" (districts), and famous for its Palio, a medieval horse race taking place twice a year in the Piazza del Campo square. Today we'll taste the energetic Panforte, the typical Siena spice cake, made out of nuts and candy fruit, a perfect snack for bike riding!

Day 7: Siena to San Gimignano

Across the Val d'Elsa up to the Manhattan of Medieval times

Shortly after leaving Siena we meet the ancient walled village of Monteriggioni. Its medieval walls are almost intact, covering a length of 570 meters and interspersed with 14 towers and two gates, the Porta Franca (towards Siena) and Porta S.Giovanni (towards Florence). The village was built by Siena on a hill dominated and monitored by the Via Cassia / Francigena. Its ideal position made it possible to control the valleys in the direction of Florence, a historic rival of Siena, which at that time was visibly expanding its territory.
The ride will lead us to San Gimignano, an Unesco heritage site thanks to its many scenic towers and its long history, one of the first independent communes of Italy. Make sure to have time to have an aperitif with a proper Vernaccia di San Gimignano, ancient wine with a distinctive character.

Day 8: Arrivederci!

Well, it’s time to say goodbye, but we are sure this part of Italy will touch your hearts and you’ll come again to visit more!