A bike trip through the purest beauty! This memorable bike tour takes you to the heart of Tuscany, among vineyards known for superfine red wines, olive groves, and hills designed by cypresses, wonderful historical centers, and cheerful locals.
Fascinating moments on the bike await you. From the twisted ups and downs through rolling hills to the exciting passages under the ancient walls of medieval towns. From the vineyards of Brunello d Montalcino and Nobile di Montepulciano to the farmhouses surrounded by olive groves. From the museum cities of Florence and Siena to the legendary places of the Eroica.
Prepare your legs and your heart for an unforgettable bike holiday!
Best of 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 from 100 km per day with at least 1000 mt of climbing per day. Those tours are designed for avid cyclists that belong to the local club and ride regularly. Usually, you are back at the hotel late afternoon.
For guests that want more riding, we can add extra loops to regular stages.
70 – 100km / 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
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!
Through the Chianti Classico wine-growing area
Today, your Best Tuscany Bike Tour will cross the legendary territories of Chianti Classico. Legend has it that a knight from Florence galloped across the territories at dawn with a black rooster to challenge the city of Siena, aiming to settle their disputes and establish a definitive border between the two rival cities.
Today, Chianti Classico is a trademark representing a specific wine production method, renowned worldwide, and is easily identified by the legendary black rooster in its logo. A history spanning over 300 years, which began in 1716, when Cosimo III, the Grand Duke of Tuscany, set the boundaries of the Chianti wine production area.
The ride in Chianti classico area goes through vineyards, wineries, woods, and fascinating villages. We are also entering the territories that host the legendary Eroica cycling race, which takes you back to the romantic dusty atmospheres of cycling of the past, made up of little technology, effort, and a lot of passion.
Overnight: Gaiole in Chianti
On the legendary roads of the Eroica
You are entering the realm of Eroica, the iconic vintage bike ride across the Chianti region. Here, you’ll get a thrilling taste of the Strade Bianche experience, riding on gravel roads with well-trodden surfaces that promise fun and romance.
Another highlight is the city of Siena, which you’ll encounter halfway through your journey. This vibrant and authentic city is considered Tuscany’s most medieval town. It’s divided into ‘Contrade’ or districts and is famous for its Palio, a medieval horse race held twice a year in Piazza del Campo. In Siena, take the opportunity to sample the energizing Panforte, a local spice cake with nuts and candied fruit that’s perfect for refueling during your ride.
Your route will then take you through the ‘Crete Senesi,’ characterized by rolling hills, isolated farmhouses, and small churches, leading you to a cozy Agriturismo in the Asciano countryside.
It will be a long day that tires your legs but fills your heart with unforgettable experiences.
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.
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
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.