Tuscany is one of the most beautiful and famous destinations for a bike tour. Cities such as Florence, Siena, San Gimignano, and Pienza are examples of Renaissance architecture and are listed as UNESCO World Heritage sites.
Visiting these places by bicycle, pedaling through the hills and Sangiovese vineyards in the Chianti Classico region is the perfect cycling holiday: peaceful countryside, excellent backroads, tasty food, renowned wine, and cheerful locals.
This bike tour is suitable for all cycle tourists. Perfect for hybrid bikes, fantastic for e-bikes which help overcome some hills, and also excellent for avid cyclists who prefer road bikes.
If you’re new to Tuscany or wish to explore it in the most immersive way, this bike tour from the saddle is the perfect choice.
Classic Tuscany | Self-Guided Bike Tour
From San Gimignano to San Gimignano
Self-Guided Bike Tour
A Self-Guided Bike Tour is a type of cycling adventure where you have the freedom to plan and navigate at your pace. Our dedicated tour guide and support team will handle hotel bookings, logistics, and baggage transport, ensuring you enjoy a hassle-free and carefree experience.
Stages up to 70 km per day with a maximum of 1300 meters of climbing. Those tours appeal to riders used to train a bit, with some “tasty” climb. Usually you are back at the hotel in the early afternoon.
For guests that want more riding, we can add extra loops to regular stages.
40 – 60km / day
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
An Epic day along the Eroica roads
A Classic bike tour in Tuscany can’t start without a wonderful ride through the Sangiovese vineyards. This will be the scenario you’ll cross when leaving San Gimignano 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. The legend of the black rooster, the symbol of the region, and the logo of all the original Chianti wines tell how the border was made to end that neverending war. Nowadays, 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.
Overnight: Gaiole in Chianti
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.
Elisa and Andrea will host us at their agritourism with pool. Before dinner, let us taste their great extra virgin olive oil.
Across the beautiful villages of Montepulciano and Pienza
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 fantastic golden fields in summer. You’ll pass through Montepulciano, where a stop is mandatory to taste one of the best Italian wines: the Vino Nobile di Montepulciano docg.
You’ll end up in the amazing village of Pienza, known as the “ideal city” and considered to be the incarnation of a Renaissance utopia, a UNESCO World Heritage Site as well. Here, you can also taste some great Pecorino cheeses made by local shepherds settled here a few generations ago from the island of Sardinia.
In the land of the Brunello di Montalcino wine
You’ll 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 its way through barren fields, woods, olive groves, and vineyards, of course, beautiful 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 lucky, you could listen to the monks’ Gregorian chant, a unique experience.
The day’s last climb leads us to the village of Montalcino, which, in addition to the pride of a great wine, can also flaunt a beautiful medieval town.
From the vineyards of Montalcino to the rolling hills of Siena
From the top of Montalcino hill, an exciting descent takes you under the medieval walls of the ancient city of Buonconvento. Then you’ll 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 and authentic city. Siena is the most medieval town of Tuscany, divided into “Contrade” (districts), and famous for its Palio, a medieval horse race taking place twice a year in the Piazza del Campo square.
Today, you’ll taste the energetic Panforte, the typical Siena spice cake made of nuts and candy fruit, a perfect snack for bike riding!
Shortly after leaving Siena, you’ll 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).
Siena built the village 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 was visibly expanding its territory then.
The ride will lead us to San Gimignano, a Unesco heritage site thanks to its many scenic towers and long history, one of the first independent communes of Italy. Make sure to have time for an aperitif with a proper Vernaccia di San Gimignano, an ancient wine with a distinctive character.
Overnight: San Gimignano
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!
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. You can book your rental bike at the end of the reservation process.