Best of Tuscany | Self-Guided Bike Tour

Tour briefing, bike fitting and warm up ride

We suggest you arrive at Florence airport. Depending on your needs, we can provide a shuttle from Florence Airport or arrange to meet you directly at your accommodation in the city center of San Gimignano.

San Gimignano, known for its many scenic towers and long history, is a UNESCO World Heritage Site and one of Italy’s first independent communes. We will start with a mandatory toast using a local wine, such as the ancient Vernaccia di San Gimignano. Following this, we will introduce the tour in detail. After a careful bike fitting, you are ready for a warm-up ride to the picturesque medieval town, a perfect beginning to your bike tour in Tuscany.

Overnight: San Gimignano
Included: –

In the lands of Chianti Classico

On the first leg of the Best Tuscany bike tour, you’ll leave behind the towers of San Gimignano, and head towards the beautiful countryside north of the town.

At the end of the long descent towards the Elsa River, you can stop for a coffee in the pretty village of Certaldo, famous for being the birthplace of the poet and novelist Giovanni Boccaccio. Here, you can visit his house or relive the amusing scenes told in his Decameron, such as the famous one of Friar Cipolla (onion) set between the alleys and the village church.

The itinerary continues through the Sangiovese vineyards of Val di Pesa in the heart of the Chianti Classico area and then leads us to the hills overlooking Florence, from which you will enjoy one of the most beautiful urban views in the world!

Overnight: Florence
Included: Breakfast

Today you leave Florence and slowly enter the rolling hills of Chianti Classico. The city fades behind you, and the road begins to move through olive groves and vineyards. After Osteria Nuova and Capannuccia, along Via di Castel Ruggero, the landscape opens wide. Stone farmhouses, cypress trees, and long views over the valleys set the rhythm of the day.

You ride toward Greve in Chianti, the historic market town that has always been a meeting point for wine growers and farmers. Its main square is a good place for a short stop before continuing along the famous Via Chiantigiana. This road is one of the symbols of the region, connecting villages and estates through gentle climbs and fast descents.

Passing through Greti and climbing toward Panzano in Chianti, you enter the heart of the Black Rooster territory. Vineyards stretch in every direction, and small wineries sit quietly on the hillsides. This is also the land of the legendary L’Eroica, the cycling event that celebrates vintage bikes and the white gravel roads of Tuscany, where passion matters more than speed.

From Lucarelli, the final stretch brings you to Radda in Chianti, a medieval village perched on a hilltop. Narrow streets, old stone walls, and wide views over the countryside welcome you at the end of the stage. It’s a ride full of history, wine culture, and the timeless atmosphere that makes Chianti unique

Overnight: Radda in Chianti
Included: Breakfast

At the origins of Chianti Classico wine

Let’s cross the Chianti region, 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, he was a researcher and wine entrepreneur of great foresight. After years of research and experimentation, in 1872, the Baron finally defined a method that became the official formula for producing Chianti wine.

You’ll pedal coasting the fortified walls of the Castle. Then, you’ll immerse yourself in the vineyards in the valley. You could have an aperitif at the classy Rapolano Thermal Baths, with great views over the bare Senesi Hills.

Overnight: Asciano
Included: Breakfast

In the land of Nobile di Montepulciano and Brunello di Montalcino wines

Today, you’ll 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.

Then we get to the 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, you’ll taste some great Pecorino cheeses made by local shepherds settled here a few generations ago from the island of Sardinia. We leave the romantic Renaissance atmosphere of Pienza, heading towards the kingdom of Brunello di Montalcino, one of the world’s most renowned and precious wines.

The itinerary winds through barren fields, woods, olive groves, and vineyards 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 lucky, you could listen to the monks’ Gregorian chant, a unique experience.

The day’s last climb leads you to the beautiful medieval village of Montalcino.

Overnight: Montalcino
Included: Breakfast

Towards the towers of medieval Manhattan

Your Best Tuscany bike tour continues along beautiful landscapes that seem to have been drawn by a Renaissance painter. Ten kilometers of descent take you down from the Brunello’s land to Val d’Arbia where we’ll cross the capital of the Val D’Arbia region.

After the neat village of Buonconvento, surrounded by fortified walls dating back to the XIV century, the route climbs to the village of Murlo, with a significant agricultural heritage and inhabited since Etruscan times.

Then, a very relaxing long stretch between fields awaits us. The small town of Casole Val d’Elsa is the ideal place to stop for a break and have a quick but tasty meal.

Finally, we arrive at the towers of San Gimignano, which are among the best examples of urban architecture created by the rich Tuscan merchants of the late Middle Ages.

Once in town, relax in the wonderful Piazza della Cisterna in front of a glass of the noble Vernaccia di San Gimignano wine or an ice cream from the historic Dondoli Gelateria, the perfect end of a memorable day.

Overnight: San Gimignano
Included: Breakfast

Arrivederci Amici!

It’s time to say goodbye, but we know that Tuscany touched your heart and you want to be back in the Med in one of Mediterras bike tour destinations!

Overnight: –
Included: Breakfast