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Strade Bianche Bike Tour

A Week of White Gravel in Tuscany

6 days / 5 nights Level: 4Price From: $5,995Collection: Challenge

Tour Highlights

Tuscany’s famed white gravel roads have gained notoriety among professional cyclists and fans alike because of one race—Strade Bianche. Between the undulating terrain, unpredictable spring weather, and unpaved gravel surfaces, the event has reached iconic status in its short history.

DuVine opens doors to the cycling-crazed enclave in and around Siena as only we can: with five-star accommodations just steps from the race village, rides along some of the most thrilling sections of the parcours one day before the pros, access to roadside action on race day, and the opportunity to join the Gran Fondo Strade Bianche.

All week long, you’ll ride our custom Cannondale Synapse Di2 bikes equipped with Vittoria Terreno Dry gravel tires and enjoy pro-level treatment before, during, and after your rides, thanks to a dedicated support team of guides, soigneurs, and mechanics. Plus, complimentary Rapha x DuVine gear, including a custom jersey, socks, and cycling cap, outfit you along the way.


Hand-rolled pici pasta, pecorino cheese, truffles, fava beans, artichokes, chestnuts, porcini mushrooms, Chianina beef, and cinghiale (wild boar)


World-famous wines made from native Sangiovese grapes including Brunello, Chianti Classico, and Vino Nobile; international blends known as Super Tuscans; and—in classic Italian fashion—espresso and cappuccino

As featured in:
Print Itinerary
  • Day 1

    Ciao Bella Toscana!

    Your guides will meet you at the Chiusi train station for a transfer to our first hotel in the Tuscan hilltop hamlet of San Quirico D’Orcia. Enjoy a light lunch in town before getting fitted to your bike. We won’t waste any time hitting the famous white roads of Tuscany—the strade bianche—starting just three miles into our first ride. It feels like a return to the 13th century as we course along ancient paths, passing through the Orcia Valley and Pienza. Here, do as the Italians do and stop for a coffee in the town’s oldest bar, then return to our hotel on routes known only to local cyclists. Tonight we dine at our hotel and learn the true meaning of buon appetito.

    Meals: Lunch / Dinner
    Destinations: San Quirico D’Orcia, Pienza
    Accomplished: 26 miles / 42 km (16 km of which are on gravel roads), elevation gain: 2,253 feet / 687 meters
    Accommodations: Palazzo del Capitano

  • Day 2

    A Taste of L’Eroica Montalcino

    L’Eroica—meaning “The Heroic”—is an event that celebrates the golden age of cycling. It takes place every October when thousands of hardened cyclists travel back in time to ride these gravel roads on primitive machines of the past. The heavy lugged-steel bikes with down-tube shifters and impossible gear ratios are no match for the red wine in the participants’ water bottles and the hardman (and hardwoman) mentality. Today, we’ll get our own taste of cycling’s heroic origins as we join one of the toughest gravel sections of L’Eroica Montalcino: a 14-kilometer climb where the maximum gradient is a challenging 12 percent. Ride through the heart of Brunello di Montalcino, Tuscany’s most celebrated wine region, and stop for lunch at a winery owned by a passionate local and former pro cyclist whose business honors the region’s rich cycling history. We’ll continue through the town of Castiglione d’Orcia before returning to our hotel, where our soigneurs are waiting to reward us with well-deserved massages. Tonight, we’re invited to a very special farm-to-table dinner, prepared with ingredients that are crafted completely by local hands.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Buonconvento, Castiglion del Bosco, Castiglione d’Orcia
    Accomplished: 56 miles / 90 km (33 km of which are on gravel roads), elevation gain: 6,400 feet / 1,951 meters
    Accommodations: Palazzo del Capitano

  • Day 3

    Strade Bianche Pro Race Recon

    All the professional teams have arrived in Siena, ready to test their legs on tomorrow’s race course. We will do the same, previewing the final 54 kilometers of the men’s pro course which also appears on Sunday’s Gran Fondo route. Team cars and pro riders will cross paths with our peloton as we pass through the mythical Monte Sante Marie gravel section dedicated to Fabian Cancellara—the only rider to win the race three times. We arrive in Siena via the infamous Santa Caterina climb, emerging into the iconic Piazza del Campo where lunch is waiting. In the afternoon, our pro soigneurs will prepare our legs for the big cycling weekend ahead. Tonight, explore Siena on your own for dinner—your guides can share their favorite trattorias or where to find the best truffle dishes in town.

    Meals: Breakfast / Lunch
    Destinations: Asciano, Castelnuovo Berardenga, Siena
    Accomplished: 55 miles / 88 km (28 km of which are on gravel roads), elevation gain: 5,206 feet / 1,587 meters
    Accommodations: Grand Hotel Continental Siena

  • Day 4

    All the Action of Strade Bianche Race Day

    The excitement of race day is in the air! Wake up at the center of the cycling world and walk to see the women’s race depart, then mingle at the buzzing team buses before we take a spin of our own. It’s a short ride to lunch at our friend Serena’s house and in true Italian fashion, she’s spent days at the stove in anticipation of our arrival. This afternoon, witness firsthand the speed and fury of the Strade Bianche race, in which professionals like Tadej Pogačar, Wout van Aert, and Julian Alaphilippe battle over the same gravel roads we’ve been riding. We’ll practically touch the action as it speeds past Serena’s house— don’t be rattled if the pros take one of the steepest gravel sections a bit faster than we did. After the race breezes by, take a lift in the van to our hotel in the heart of Siena. Tonight’s dinner at the best pizzeria in town will fuel us for the challenge that awaits us tomorrow.

    Meals:  Breakfast / Lunch / Dinner
    Destinations: Pieveasciata, Pianella
    Accomplished: 24 miles / 39 km, elevation gain: 2,007 feet / 612 meters
    Accommodations: Grand Hotel Continental Siena

  • Day 5

    The Gran Fondo Strade Bianche

    Now that we’ve feasted on fine food and wine, tested our legs on some of the region’s precipitous climbs, and refined our technical skills on gravel roads, it all culminates in the Gran Fondo Strade Bianche. The annual big ride includes some of the most challenging sections of gravel in Bella Toscana! Wake up in the medieval walled city of Siena—our hotel is mere meters from where the legendary route begins and ends hours later, after the brutal climb up Via Santa Caterina and the finish in Piazza del Campo. After the race, we’ll regroup in the city center and have lunch before recovering at the hotel with another treatment from our soigneur. Tonight, reflect on a fabulous week of riding as we indulge in a celebratory dinner at one of Siena’s best restaurants.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Siena
    Accomplished (Medio Fondo): 54 miles / 87 km (22 km of which are on gravel roads), elevation gain: 4,176 feet / 1,273 meters (545 meters on gravel)
    Longer Option (Gran Fondo): 86 miles / 139 km (55 km of which are on gravel roads), elevation gain: 6,668 feet / 2,033 meters (1,285 meters on gravel)
    Accommodations: Grand Hotel Continental Siena

  • Day 6


    Our last morning in Tuscany presents plenty of options: sleep in, savor a slow breakfast, or take a final stroll around Siena. Your guides will return you to the Siena train station, bidding you farewell before you depart for your next destination.

    Meals: Breakfast
    Destinations: Siena, Chiusi

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Rome or Florence, Italy Pick-Up Location: Chiusi train station Pick-Up Time: 11:00 am
Departure Details

Airport City: Rome or Florence, Italy Drop-Off Location: Chiusi train station or Siena train station Drop-Off Time: 11:00 am

Please note that Arrival + Departure Details for 2025 tours could be subject to change.
Travelers Take Note

Upon booking this tour, you will be asked to complete a short form. We use this information to ensure all Level 4 trip participants are adequately prepared for our most difficult riding and have proximate cycling experience to the rest of the group.

Given the nature of the biking and the roads on this route, you will be riding on gravel every day. Please note that e-bikes cannot be reserved for this tour.

To participate in the Gran Fondo Strade Bianche, you must complete a mandatory health certificate and have it certified by your physician prior to traveling.

Weather by Month

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  • Thoughtfully selected accommodations that reveal the true character of the region in ideal riding locations
  • Luggage transfers


  • Daily breakfasts, all lunches, and 4 cyclist-friendly dinners at our favorite local restaurants and renowned culinary establishments
  • Nutritious energy snacks, hydration, and shakes to support endurance and recovery
  • Local wines and beer with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line Cannondale carbon fiber road bike
  • Exclusive Rapha x DuVine jersey, socks, and cycling cap
  • Complimentary DuVine gear, including a DuVine t-shirt, water bottle, and drawstring bag
  • GPS with pre-programmed route maps


  • Expert bilingual guide with extensive cycling experience and local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Laundry service provided mid-week
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs

Synapse 2 RLE Custom

Manufacturer: Cannondale

Type: Road

Included in trip price