Best of 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 Florence

In the lands of Chianti Classico

We leave behind the towers of San Gimignano, and head towards the beautiful countryside north of the town. At the end of the long descent that slopes down 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) which is set right between the alleys and the church of the village. 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!

Day 3: Florence to Gaiole in Chianti

Through the Chianti Classico wine-growing area

Today you will cross the legendary territories of Chianti Classico those that, according to the legend of the black rooster, were crossed at dawn at a gallop by the knight of Florence, in the challenge with the city of Siena launched to put an end to the disputes and establish a definitive border between the two rival cities. Today Chianti Classico is the trademark of a wine production specification, undoubtedly one of the most famous in the world, in whose logo the legendary black rooster always stands out. 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. This means that we will go through vineyard and wineries, but in fact not only because there will also be 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.

Day 4: Gaiole in Chianti to Asciano

On the legendary roads of the Eroica

We are 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 other highlight of the day is undoubtedly the city of Siena, that you will meet about halfway through. Siena is a lively but still authentic city, it's considered 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. Here you'll have the chance to taste the energetic Panforte, the typical Siena spice cake, made out of nuts and candy fruit, a perfect snack for bike riding! Then you go through the typical landscapes of the "Crete Senesi", made up of rolling hills, gullies, lonely farmhouses, and small parish churches, up to your cozy Agriturismo in Asciano countryside. A long day that will have tired your legs but filled your heart with precious experiences

Day 5: Asciano to Montalcino

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

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. Then we get to 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. 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 San Gimignano

Towards the towers of medieval Manhattan

Your tour continues along a beautiful landscapes which seems drawing by a Renaissance painter. Ten kilometres of descent take you down from the Brunello's land to Val d'Arbia we’ll cross the capital of Val D’Arbia region. After the neat village of Buonconvento, surrounded by fortified walls dating back to XIV century, the route climbs to the village of Murlo, with a quite strong 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, the arrival among the towers of San Gimignano, one of 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.

Day 7: Departure

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 with us!