Tuscany Gravel

Ride the famous Strada Bianche gravel
  • From $4345
  • Location Tuscany, Italy
  • Duration 7 Days / 6 Nights
  • Rider Level 2 / 3 / 4 / 5

Ride the white, gravel roads that wind through the Tuscan countryside.

We’ve added a new twist to our Tuscany itinerary and included more gravel sections of the famed white roads (aka “strade bianche”) on the Italian countryside. Legends have been made on these roads during the Strade Bianche, a one-day classic bike race that has become one of the most anticipated and watched professional cycling events. Our trip will highlight some of our favorite gravel sections of the race and sprinkle in a few lesser-known segments of gravel.


  • Daily guided and supported rides among vineyards and olive groves with an emphasis on the Strade Bianche, the white gravel roads of Tuscany
  • Eat family-prepared meals by our Italian hosts, including pizza made in a wood-fired oven
  • Stay in cozy bed-and-breakfast accommodations off the beaten path
  • Explore Siena, taste wine and try the local cuisine
  • Take part in an authentic Italian cooking class


It doesn’t get more authentic than this: Our food in Tuscany is prepared fresh by the Italian family who runs Palazzo a Merse, the bed and breakfast where we stay. Many of the meats are sourced from a farm down the road, and the veggies are grown in the field behind the property or by the neighbors across the street. Meats are cooked over an open flame, and pizzas are prepared in a 500-year-old wood-fired oven. Family B&B meals are balanced with dining out to enjoy the local cuisine.


Meet your new extended family at Palazzo a Merse, a restored 18th-century farmhouse bed and breakfast where we’ll spend the week. Owned by our guide Andréa Rossi and his wife and sister’s family, the rustic Tuscan B&B is about 10 kilometers from Siena in the quiet countryside of Val di Merse. Relax in the spacious, shady garden, or enjoy breakfast or a glass of wine as you lounge around the outdoor pool. Family-style meals are cooked by our hosts and served outside when the weather allows.


Riders will arrive at the Florence Airport or the Siena Train Station, and we will shuttle to B&B Palazzo a Merse.

Anyone renting a car can arrive at the B&B any time after 11 a.m. We’ll head out for an arrival day spin (~2 hours) to explore our surroundings for the week.

Today’s ride:

Arrival day spin:
21 miles, 1,044 feet of climbing

Today we ride point to point through the heart of Tuscany, with a stop in Pienza. The ride features quintessential Tuscany landscapes with cypress-lined gravel roads and spectacular views of the beautiful countryside. The ride will finish in Montisi, where we will enjoy lunch at one of our favorite cafés before shuttling back to the bed and breakfast.

Today’s ride:

The Heart of Tuscany Gravel: 42 miles, 4,300 feet of climbing

Learn more about the legend of that famous black rooster as we take a tour of the Chianti region. We’ll shuttle to the start, and mid-ride, we’ll enjoy a coffee stop in the village of Gaiole, where the Eroica Gran Fondo starts and finishes. The route finishes in the medieval village of San Gusme, where we’ll enjoy lunch.

After lunch, we’ll return to the B&B, where the family will host a cooking class. You’ll learn how to make homemade pasta and tiramisu (among other dishes), so when you host your next dinner party, you can show off your new skills!

Today’s ride:

Chianti Gravel: 38 miles, 3,900 feet of climbing

Today we’ll point to point across the Val d’Orcia region on our way to Il  Il Molinello Agriturismo. Here we will have lunch, tour their lavender farm, and check out their L’Eroica museum. The ride has several Strade Bianche sectors and we ride the famed white roads lined with Cyprus trees across the rolling countryside, you won’t want to miss this ride!

Today’s ride:

Val d’Orcia: 37 miles, 3,400 feet of climbing

Our route takes us North towards Pievescola into the enchanted forest. After a stop for coffee in Pievescola, we climb towards the small village of Molli. The final 15 miles are net loss and we finish back at the B&B with a relaxing lunch in the garden.

Today’s ride:

Montagnola and Sienna: 36 miles, 3,300 feet of climbing

Today guests will ride some of the most famous sectors of the Strade Bianche professional race. The finish will follow the same route as the Strade Bianche into Sienna up the steep streets towards Piazza del Campo. Here we will celebrate our fantastic week on the white roads of Tuscany with pizza, beer, and wine.

Today’s ride:

Strade Bianche: TBD


Checkout is 11 a.m. Riders will pack up, and we’ll shuttle back to the Florence Airport or the Siena Train Station for departures.

Today’s plan:

Shuttles to Siena and Florence



What's Included

  • 7 days/6 nights accommodations (double occupancy)
  • Airport transfers to/from Florence International Airport (FLR)
  • All meals (breakfast, lunch, dinner)
  • Wine tasting, Siena walking tour, cooking class!
  • Mechanical support (including bike build and breakdown)
  • Professional trip guides
  • Daily sag support
  • Ride nutrition products
  • High-quality ride photos

What's Not Included

  • Airfare
  • Bike rentals
  • Gratuity for guides
  • Mid-ride café stops
  • Personal shopping 

Optional Activities

  • Wine tasting
  • Tuscan cooking class
  • Siena walking tour


Have more questions? View our FAQ page or call us at 406-312-5770.


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Rent A Bike

Traveling through the airport with a bike—and paying for it to fly—is not everyone’s idea of a fun way to start a vacation. Fortunately, we offer high-quality, full carbon bikes on all of our trips across the United States and Europe. Want to just show up and ride? Just bring your shoes, pedals, helmet, and saddle (if you want), and rent one of ours.

Available this trip:
ParkPre Kroad
Manufacturer: ParkPre
Type: Road
Cost: $300 / trip
Italian E-Bike
Manufacturer: Univega
Type: E-Bike
Cost: $350 / trip
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Bring Your Own

Your bike is yours—we get it. Bringing your own bike has obvious advantages in terms of individual comfort. Before your trip, we suggest getting a tune-up at your local bike shop so it’s ready to roll for your week of riding. Once you arrive, we’ll be sure to have our mechanics build it and help with any necessary tweaks. Check out some helpful resources here:

Shipping your bike

Flying with your bike.

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Skip The Bike

If you or your travel partner want to enjoy the trip and explore a new destination without a bike, drop us a line and we’ll discuss options. Some trips are better suited for non-rider participants than others.