Tuscany Gravel Cycling Tour

Upon your arrival in Siena, you’ll check into your hotel and have the chance to settle in and explore this charming city on your own. You can wander through the winding streets and alleys, and take in the city’s stunning medieval architecture and famous Piazza del Campo.

After dinner, you can retire to your hotel for a good night’s rest, as you’ll need to be well-rested for the start of your cycling adventure tomorrow.

Start your day by cycling through the stunning Val d’Arbia region, taking in the rolling hills and beautiful views along the way. This section of the ride follows the famed L’Eroica route, offering a unique and unforgettable experience.

Continuing on the L’Eroica route, you’ll make your way up to Castiglion del Bosco, where the scenery changes to charming Brunello vineyards that stretch as far as the eye can see.

The final leg of your journey takes you to San Quirico d’Orcia, a beautiful medieval town located in the heart of Val d’Orcia. Take a break to explore the town’s winding streets and enjoy the views.

Today’s route takes you through the stunning Val d’Orcia region, widely regarded as one of the most beautiful places in Tuscany and a UNESCO World Heritage site.

Following the Via Francigena road, you’ll arrive at Bagno Vignoni, a charming village with a unique main square – a big thermal pool that contains the original source of thermal water. Next, you’ll ride along a gravel road to Monticchiello, a small medieval town with a lot of charm.

After Monticchiello, you will make a quick stop at Montepulciano to explore the town’s winding streets and squares. This town is known for its beauty and is an excellent spot for some memorable photos.

The next destination on the route is Pienza, known as the “ideal” city of the Renaissance era and famous for its delicious Pecorino cheese. The route ends with a visit to the Chapel of Vitaleta, a small church located in the middle of the wheat fields.

Today’s stage includes a long stretch on gravel roads with breathtaking views of the Crete Senesi.

As you cycle along the Eroica route near Lucignano d’Asso, you’ll encounter one of the most fascinating white roads of the entire route. Take a moment to appreciate the stunning surroundings before continuing on your journey.

You will take a break in Buonconvento, one of the most beautiful villages in Italy. Wander through the village’s charming streets and squares, and perhaps stop for a coffee or a bite to eat.

Continuing on the route, you’ll pedal on the sector of San Martino in Grania, a part of the course used by professional cyclists during the Strade Bianche race.

The day ends in Asciano, where a stop in the center of the village is a must. Take some time to explore this charming town and relax after a day of cycling.

This day’s stage starts with a challenging ride along the gravel road of Monte Sante Marie, which has played a significant role in the history of L’Eroica and the professional race Strade Bianche.

As you cycle up Monte Sante Marie, you’ll reach the edge of the Chianti region, a stunning area known for its wine and picturesque scenery. You’ll encounter a technical segment in the middle of the vineyards of Villa Arceno, leading to the pretty village of San Gusmè.

Continuing on the route, you’ll pass through Villa a Sesta and the Castle of Brolio, the symbol of Chianti that has been owned by the Ricasoli family since 1141.

You’ll arrive back in Siena feeling accomplished and invigorated from your journey through Tuscany’s breathtaking landscapes.

This is the end of your unforgettable journey through the stunning landscapes of Tuscany. As you prepare to depart, take a moment to reflect on the experiences you’ve had, the memories you’ve made, and the breathtaking beauty of this incredible region.

You will take with you the memories and the knowledge that you have truly experienced the best that Tuscany has to offer. And remember, you’re always welcome back to this magical region, where adventure, beauty, and inspiration await at every turn.