Cycling through some of Tuscany’s most pristine and picturesque gravel roads
Visiting famous Tuscan destinations such as L’Eroice and Chianti
Sampling world-renowned wine and cheese, including the famous Pecorino cheese
Experiencing Tuscany’s natural beauty up close and personal, from rolling hills to vineyards and olive groves
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.
Hotel in Siena
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.
Hotel in San Quirico d’Orcia
70km, 1100m elevation gain
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.
55km, 1150m elevation gain
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.
B&B in Asciano
50km, 600m elevation gain
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.
60km, 1350m elevation gain
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.
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Tour design and organization
Booklet with detailed itinerary and route instructions
Service and support during your tour
GPS navigation with an easy-to-use app
Accommodation as per itinerary
Starting in the charming city of Siena, you’ll embark on a journey that will take you through some of the most breathtaking landscapes that Italy has to offer.
Along the way, you’ll visit some of Tuscany’s most famous destinations, including L’Eroice, Chianti, and the surrounding area where the Strade Bianche race is held every year.
As you travel along the winding gravel roads that crisscross the region, you’ll be immersed in Tuscany’s natural beauty. You’ll pass through rolling hills dotted with olive groves and vineyards, and enjoy sweeping vistas of the countryside. And because you’re cycling, you’ll be able to experience it all up close and personal.
Of course, no visit to Tuscany is complete without sampling some of the region’s famous wine and cheese. You’ll have plenty of opportunities to indulge in both, as you pass through the heart of the Chianti wine region and visit charming towns and villages that are famous for their artisanal cheeses, such as Pecorino.
But beyond the food and drink, what truly sets this Tuscan cycling experience apart is the opportunity to travel on some of the region’s most pristine and picturesque gravel roads. These roads wind through some of the most remote and unspoiled corners of Tuscany, taking you off the beaten path and providing you with a truly unique and unforgettable cycling experience.
From the challenging climbs to the exhilarating descents, every mile of this six-day journey is packed with excitement and adventure. And when you reach the end of your journey, you’ll not only have unforgettable memories to cherish, but you’ll also have a deeper appreciation for the beauty and history of Tuscany.
Our priority is to find the ideal accommodation that suits your needs. We collaborate with several lodging providers that meet our criteria, but please note that availability can be limited, particularly during peak seasons. Furthermore, we can tailor your holiday to align with your preferences and budget, and are committed to finding a more suitable alternative that matches your taste.
To ensure availability, we advise booking your tour as early as possible. Our tours typically pass through highly popular tourist destinations where lodging options are restricted. Many of these desirable locations become fully booked for the summer season well in advance, often filling up by spring.
The availability of food options in Italy depends on the extent of your dietary restrictions. While it is relatively easy to find vegetarian dishes, locating vegan meals can be challenging, particularly in smaller towns and rural areas. Additionally, the traditional lunch stops we make may have limited ability to accommodate special requests beyond their standard menu. We recommend considering this when planning your meals.
Our tours in Italy can accommodate various types of bikes, including road, gravel, and mountain bikes. We maintain constant communication with you to ensure the optimal conditions for your cycling holidays in Italy.
A versatile option for cycling in Italy is the gravel bike, even if you plan to embark on a road cycling holiday. It does not significantly affect road performance and allows you to explore scenic backroads that may be slightly rougher than the main routes. Furthermore, gravel bikes typically offer greater comfort and more control.
Italy is a diverse country with something for every cyclist. Regardless of your choice of bike, we will customize the perfect route for your cycling holiday.
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