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The Best of Tuscany Gravel

Pedal Through Tuscany’s Soul – Gravel Roads, Gourmet Tables, and Ancient Traditions, culminating with a fun-filled Gravel Bike event

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.


A dreamy gravel cycling experience on classic "Strade Bianche" white roads culminating with a fun-filled Gravel Bike event
Destination
Italy, Tuscany
Activity
Biking, Gravel Rides
Level
Intermediate
Level

Perfect for the cycling newbies who already enjoy being active, or anyone who just wants to take it easy.

Pedal at a meandering pace, stopping to take pictures, savor a leisurely lunch and explore the surroundings. Enjoy quiet roads along flat and rolling terrain zigzagging through vineyards, olive groves and farmland.

  • Average daily distance: 35-45 miles
  • Terrain: flat and rolling

Our Athletic Beginner tours are perfect for those who aren’t avid cyclists, but are fit and love to exercise regularly.

On these trips, you’ll enjoy a flowing pace with plenty of time throughout the day to indulge in the local specialties, take in the local culture and enjoy the magnificent views. There will be an occasional hill, more rolling terrain and higher mileage than an Easy tour.

  • Average daily distance: 35-45 miles
  • Terrain: flat and rolling
  • Our guides will offer cycling clinics and one-on-one coaching in cadence, positioning and the art of shifting efficiently on rolling hills.

You love being active and cycling is your preferred way. You are in good physical condition and ride whenever you can.

Intermediate tours maintain a steady pace with opportunities to push yourself by tackling challenging climbs with great descents over stunning terrain. You’ll still have time to explore and enjoy the landscape and towns you’ll visit.

  • Average daily distance: 40-50 miles
  • Terrain: rolling with some hills

You are an avid cyclist who trains regularly, participates in bicycling events and is eager to plan their next bicycling vacation. You enjoy a vigorous ride, challenging climbs and thrilling descents.

These “Epic” and “follow the race” tours are spectacular and have plenty of classic climbs and are perfect for cyclists who covet long mileage with lots of hills and varying terrain.

  • Average daily distance: 45+ miles
  • Terrain: hilly with long climbs
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Duration
8 days / 7 nights
Gravel enthusiasts or Intermediate cyclists with some gravel skills who are excited to improve.
2025
2026
From $5,280 PP 8 days / 7 nights
From $4,500 PP 8 days / 7 nights
Book Now
Schedule A Call
Download Itinerary
Gravel enthusiasts or Intermediate cyclists with some gravel skills who are excited to improve.

Discover the true essence of Tuscany on two wheels—a unique gravel cycling adventure that immerses you in the region’s landscapes, flavors, and traditions. Based at Il Molinello, a welcoming family-run agriturismo, this journey blends scenic rides with authentic Tuscan living. Over several unforgettable days, explore iconic regions like the Crete Senesi, a UNESCO World Heritage Site, Chianti, and Valdichiana via quiet gravel roads that wind through rolling hills, medieval villages, and vineyards. This is a journey through history, unfolding mainly in Siena, the Italian province with the most miles of unpaved roads. Long before the gravel boom, locals rode these peaceful, zig-zagging strade bianche to connect with nature and escape the modern world. These historic routes are also home to cycling legends—the L’Eroica vintage event and the Strade Bianche professional race.But the tour is more than a ride—it’s a taste of Tuscan life. Savor aperitivo by a 14th-century mill, homemade dinners under the stars, and experiences like olive oil tastings, a cooking class, and a guided wine tasting. Visit Siena and Cortona, meet local artisans, and unwind with optional massages or countryside strolls.

Special Event: On our May and October departures, the tour concludes with a spectacular Gravellata—a festive local ride organized by Gravel Bike Siena, a community devoted to “experiencing nature and having fun on two wheels.” Join hundreds of like-minded cyclists to pedal the iconic strade bianche through the Crete Senesi and Chianti, and feel the passion of Italy’s gravel scene. Andiamo!

Tour Essence

  • Ride through the iconic landscapes of the Crete Senesi, Chianti, and Valdichiana on curated gravel routes with breathtaking views and quiet, scenic roads.
  • Stay at il Molinello, a family-run farmhouse steeped in history and Tuscan charm—your warm and welcoming home for the entire tour.
  • Enjoy authentic tuscan cuisine at farm-to-table meals, hands-on cooking classes, and unforgettable dinners featuring local specialties like Chianina beef and homemade pasta.
  • Savor Tuscany’s finest wines and extra virgin olive oils with guided tastings led by passionate local producers.
  • Visit medieval gems like Siena and Cortona, learn about Etruscan history, and discover traditional crafts in immersive workshops.
  • Pedal challenging climbs in Chianti and relaxed recovery rides, each day offers tailored routes to suit your pace and energy level.
  • Experience true Tuscan warmth with the Molinello family, who go beyond hosting—welcoming you like lifelong friends.
  • Take part in 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% trails
Start Location
Asciano
End Location
Asciano
Mileage
Average Daily: 35 miles Total: 225 to 300 miles
Elevation
Average Daily: 3,000 ft Total: 18,600 ft
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What's Included

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.

What’s Included
  • 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
  • 1 cooking class
  • Lavender workshop
  • 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

Gravel Bike

Carbon Gravel Bike Included

E-Road Bikes

Electric Bike Call for Pricing.
  • Accommodation in an old mill from the 14th century
  • All meals
  • Entry, jersey, and water bottle of the “Gravel Bike Siena” event
  • 1 olive oil tasting
  • 1 wine tasting
  • 1 cooking class
  • Lavender workshop

Dates

2025

Oct 5-12
Available

2026

May 4-11
Available
Oct 6-13
Available
2025
2026
From $5,280 PP 8 days / 7 nights
From $4,500 PP 8 days / 7 nights
1,400/2026:$900 Single Supplement
Book Now
Schedule A Call
Download Itinerary
Any of our tours can be made private. Contact us to learn more.
Go Private
Guaranteed

Confirmed tours are dates that have been selected by us that have a very high probability of reaching the minimum group size for us to run the tour and for you to receive the best Ciclismo Classico experience. These tours are confirmed as much as a year in advance, compared to our regularly scheduled tours which are confirmed around 90 days prior to departure.  When you place your deposit for a confirmed tour, you have the green light to make your pre and post travel plans and even book your flight with our personal guarantee that your tour will run!

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Single Supplement

If you are traveling alone, this optional single supplement will guarantee you a room to yourself at each hotel. The cost of a single room is often more than half the price of a shared room, so this additional supplement reflects that increased cost for each night over the course of the trip.

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From the Blog

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Ciclismo Experience

Top 5 Reasons to Plan a Private or Custom Bike Tour with Ciclismo Classico

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Guest Stories: Jeff Gair

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Guest Stories: Tammy & Marty Washburn

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