The Best of Tuscany Gravel
White Roads Nirvana
Download a Detailed Itinerary
Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:
- A thorough daily itinerary
- Details for exact accommodations
- What to expect
- Travel planning tips
Please provide your contact information so that we can say “benvenuto”. After submitting the form, you will be able to download the itinerary immediately.
The tour is a journey through history and unfolds mainly in Siena, the Italian province with the most miles of “unpaved roads.” Even before the gravel bike boom, local cyclists have been riding these peaceful, zig-zagging white roads to be close to nature, to go back in time, and to escape the world of asphalt and cars. These routes have a rich historical significance and are part of the L’Eroica vintage event and the “Strade Bianche” professional race. They include iconic stretches such as the Monte Sante Marie climb and the San Martino in Grania road.
Our trip covers some of the most important areas of Tuscany, such as the “Crete of Siena,” a UNESCO World Heritage Site, the Val d’Orcia, and the undisclosed Val di Merse.
Special Event: On the last day of our Tuscany Gravel tour in May and October, we have a grand finale experience planned. We will be partnering and participating in a special local “Gravellata” event organized by Gravel Bike Siena, a team of all “lovers of dirt” whose simple mission is to “experience nature on their bikes and to have fun together.”
Each Gravel Bike Siena event attracts hundreds of like-minded, fun-seeking lovers of Slow Cycling to enjoy the most beautiful “Strade Bianche” (white roads) of the Crete Senesi and the Chianti region. You will not only experience an exceptional cycling event, but you will also be immersed in the passion of the Italian gravel cycling community. Andiamo!
Tour Essence
- Ride the historic “Strade Bianche” of Siena province
- Join hundreds of passionate and local “gravellisti” at the “Gravel Bike Siena” ride of a lifetime
- Discover the charming medieval towns of Montalcino and San Quirico and the historical center of Siena, the most authentic Tuscan city
- Ride in the UNESCO World Heritage sites of Crete Senesi, Val d’Orcia, and the lesser-known Val di Merse
- Learn more about exceptional Tuscan wines and extra virgin olive oil
- Taste traditional and gourmet meals made with locally produced ingredients
- Experience the joy, laughter, music, great food, and camaraderie of a Tuscan gravel event and after-ride party
Exclusive for May Departure:
- Participate in the “80 voglia di Gravel” (I Crave Gravel) event when the landscape is bursting and blooming
Exclusive for October Departure:
- Participate in the “Castello di Monteriggioni” event in the fall when Tuscany is golden, and the snack stops are overflowing with delicious Tuscan Specialities fresh from local harvests
What to Expect
Terrain
Hilly, 40% pavement, 45% white roads, 15% trailsStart Location
AscianoEnd Location
SienaMileage
Average Daily: 32 miles Total: 223 to 298 milesElevation
Average Daily: 2,500 ft Total: 18,000 ft
Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Service of professional guides throughout the program
- Full van support
- Ciclismo jersey and water bottle
- Cycling clinics and one-on-one coaching
- Entry, jersey and water bottle of the “Gravel Bike Siena” event
- 1 olive oil tasting
- 1 wine tasting and tour of wine estate
- Guided walking tour of Siena
- Shuttle at the beginning and at the end of the tour
- Use of our exclusive carbon gravel bike, La Ribelle Gravel (or Equivalent Carbon Gravel Bike)
- Garmin Edge Explore GPS loaded with the GPX tracks of your rides
- Two water bottles
- Saddle bag with repair kit
- Optional: map holder on handlebar
Pedal Options:
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless/SPD pedals with shoes
- Optional: your own saddle
- All accommodations
- All breakfasts
- 2 lunches
- 6 dinners
- Entry, jersey and water bottle of the “Gravel Bike Siena” event
- 1 olive oil tasting
- 1 wine tasting and tour of wine estate
- Guided walking tour of Siena
2025
Start Location
AscianoFly Into
Florence, italyEnd Location
SienaFly Out Of
Florence, ItalyAsciano warm-up ride
Meals Provided
Lunch, DinnerAverage Mileage
16 milesElevation Gain
1,200 ftRiding Terrain
Rolling with a few hillsMeals Provided
Lunch, DinnerAccommodations
Agriturismo Il Molinello
Agriturismo Il Molinello is a renovated farmhouse where our Top Guides, Sandro and Guido, live, offering a back-to-nature experience. Gentle hills and stunning scenery surround the beautiful location in the characteristic Tuscan landscape outside of Siena.
Strade Bianche Loop
Meals Provided
Breakfast, DinnerAverage Mileage
38 milesElevation Gain
3,036 ftRiding Terrain
Rolling with a few hillsMeals Provided
Breakfast, DinnerAccommodations
Agriturismo Il Molinello
Agriturismo Il Molinello is a renovated farmhouse where our Top Guides, Sandro and Guido, live, offering a back-to-nature experience. Gentle hills and stunning scenery surround the beautiful location in the characteristic Tuscan landscape outside of Siena.
Montalcino
Meals Provided
Breakfast, DinnerAverage Mileage
34 milesElevation Gain
3,945 ftRiding Terrain
Rolling with a few hillsMeals Provided
Breakfast, DinnerAccommodations
Canalicchio di Sopra Wine Relais
The 5-star hotel Borgo Canalicchio di Sopra is a captivating place that blends nature’s splendor with attention to detail. It is a wine resort where you can enjoy a unique experience. The hotel boasts elegant spaces, luxurious 5-star comforts, and two swimming pools, one with a hydromassage.
Val d'Orcia
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
41 milesElevation Gain
4,106 ftRiding Terrain
Rolling with a few hillsMeals Provided
Breakfast, Lunch, DinnerAccommodations
Canalicchio di Sopra Wine Relais
The 5-star hotel Borgo Canalicchio di Sopra is a captivating place that blends nature’s splendor with attention to detail. It is a wine resort where you can enjoy a unique experience. The hotel boasts elegant spaces, luxurious 5-star comforts, and two swimming pools, one with a hydromassage.
Val di Merse
Meals Provided
Breakfast, DinnerAverage Mileage
32 milesElevation Gain
2,679 ftRiding Terrain
Rolling with a few hillsMeals Provided
Breakfast, DinnerAccommodations
Relais Le Macine di Stigliano
The 4-star Relais Le Macine di Stigliano is located in the village of the same name. Through the meticulous restoration of the original medieval Sienese stronghold, a haven of tranquility emerges, boasting ten welcoming and relaxing rooms and a swimming-pool. Each room is furnished with taste and elegance and equipped with all modern comforts.
Siena
Meals Provided
BreakfastAverage Mileage
32 milesElevation Gain
3,042 ftRiding Terrain
Rolling with a few hillsMeals Provided
BreakfastAccommodations
Villa del Sole
4-star Villa del Sole is a boutique hotel in one of the most picturesque corners of the historic center of Siena, overlooking the greenery of Orti de’ Pecci. Each room combines modern design with precious details to offer absolute relaxation—a wide range of services and accessories in a comfortable environment decorated with paintings by famous local artists.
"Gravel Bike Siena" Event
Meals Provided
Breakfast, DinnerAverage Mileage
Several lengths options possibleRiding Terrain
Rolling with a few hillsMeals Provided
Breakfast, DinnerAccommodations
Villa del Sole
4-star Villa del Sole is a boutique hotel in one of the most picturesque corners of the historic center of Siena, overlooking the greenery of Orti de’ Pecci. Each room combines modern design with precious details to offer absolute relaxation—a wide range of services and accessories in a comfortable environment decorated with paintings by famous local artists.
