Eroic “Strade Bianche” Tuscany Bike Tour

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From Pienza, the Eroica town of Val d’Orcia to Gaiole in Chianti!
The Famed “Strade Bianche” of Tuscany!

These white, dusted roads are home to one of pro cycling’s biggest dates, with steep climbs and full-blown attacks at every bend. The Strade Bianche is truly something unique and special to experience. The region’s rolling hills and fine wines make this a must destination if you love gravel cycling.
Discover the route of the Strade Bianche professional race – We put together this self guided Bike Tour selecting sections from the race combined with sections of L’Eroica as your tour itinerary from March to November.
Like the L’Eroica, you will visit towns of Gaiole and covers some of the most beautiful roads in the provinces of Chianti and Siena, winding among historic vineyards, leading to the cypress-lined entrance of Castello di Brolio and Corte Pavone.

Carbon frame GRAVEL bike or E-bike are perfect to face this tour.
Choose between Scott Gravel Addict 20 Or Scott E-SUB Cross 10

Not to be missed:

  • Follow the hilly path of L’Eroica, Tuscany’s internationally recognized vintage bike race.
  • Explore ancient cellars, taste superb Tuscan wines; from Vino Nobile di Montepulciano to Brunello di Montalcino.
  • Experience the serenity of the Tuscan countryside and savor the flavors of authentic pasta fresca and local cheeses.
  • Explore the undulating white gravel roads of Tuscany—the famed Strade Bianche, and immerse yourself in Italy’s most classic cycling location.
  • Treat yourself with Caffé espresso, cappuccino & the best gelato!

Day by Day

Day 1: Pienza & Bagno Vignoni
Short Bike Test in Pienza. Distance: 25 km /15 miles
Difficulty: Easy to Moderate; 12 km asphalt and 13 km gravel
Meet & Greet in Pienza; the purest Renaissance town in the world for welcomeing and bike fitting. Pienza; the is a remarkable example of Renaissance-era town planning. First, a short bike ride to Bagno Vignoni, a thermal spa town that dates back to Roman times and the Madonna di Vita Leta chapel.
Lodging at hotel Relais Il Chiostro di Pienza

DAY 2: Montepulciano & Vino Nobile (Nobile Wine)
Loop Bike Ride in Pienza. Distance: 51 km/31,5 miles
Difficulty: Moderate; 17km asphalt and 34km gravel
Loop bike ride from Pienza. Spring brings red poppy blossoms to the vibrant green wheat fields of Tuscany, and nowhere is the bloom more brilliant than the hills of the Val d’Orcia, a UNESCO World Heritage Site lined with corridors of proud cypress trees. Follow the gravel roads off the beaten path and enjoy an espresso at La Foce. By lunchtime you’ll arrive to Montepulciano, the jewel of southern Tuscany. Return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.
Lodging at hotel Relais Il Chiostro di Pienza.

DAY 3: Pieve a Salti to Brunello Land
Bike Ride from Pienza to Montalcino. Distance: 41 km /25 miles
Difficulty: Moderate; 17 km asphalt and 24 km gravel
Today we selected the sections of Eroica called Lucignano d’Asso and Pieve a Salti. Leave Pienza and follow the white roads toward Cosona to the little hamlet of Lucignano. Start the other Eroica gravel section of Pieve a Salti 9 km up and down in the rural countryside! Arrive in Buonconvento in time for lunch. After lunch, face the climb to the famed wine town of Montalcino all through vineyards and wineries. For dinner, reward yourself at least a glass of Brunello – we have a list of our favorite.
Lodging at hotel il Giglio in Montalcino

DAY 4: Castiglion del Bosco & Siena
Bike Ride from Montalcino to Siena. Distance: 56 km /35 miles
Difficulty: Moderate to Challenging; 32 km asphalt and 24 km gravel
L’Eroica, meaning “The Heroic” takes place every October when thousands of hardened cyclists travel back in time on heavy lugged-steel bikes with down-tube shifters and impossible gear ratios and hard-man mentality. Today, we’ll ride one of the most beautiful gravel sections of L’Eroica. From the heart of Brunello di Montalcino, ride to the top of Passo del Lume Spento; which starts the Castiglion del Bosco gravel section. Once in Bibbiano, another 30km section called la Piana to reach Murlo. From here another legendary Eroica section to Radi, with some steep yet short rolling hills. A light lunch in Ville di Corsano you before returning to Siena.
Lodging at hotel Villa str in Siena

DAY 5: Gaiole, the Eroica town
Bike Ride from Siena to Gaiole. Distance: 46 km /28,5 miles
Difficulty: Moderate to Callenging; 12 km asphalt and 34 km gravel
Today’s destination is the town where the Eroica starts heading out into magical Chianti. Exit Siena via a Eroica gravel section of Pieve a Bozzone, Vico dArbia cycling 15km through rolling wheat fields to the wine region of Pianella. Pedal to Canonica a Cerreto, Vagliagli through Chianti Classico vineyards where you can’t help but count castles and old hilltop hamlets! Reach Radda in Chianit in time for lunch then in to Gaiole to relax.
Lodging at the charming Hotel Castello Spaltenna

DAY 6: Chianti hills – Castello di Brolio
Bike Ride from Gaiole to Castellina. Distance: 54 km /33,5 miles
Difficulty: Moderate to Challenging; 44 km asphalt and 10 km gravel
Explore the villages and hamlets of Chianti Senese. Start from Gaiole and bike to Castello di Brolio. After a nice coffee stop, ride a short gravel section of the Eroica and on secondary scenery roads until reaching Castelnuvo Berardenga, just in time for lunch. Back on the saddle and encounter other small Borgos: San Gusmé and Villa a Sesta – back to Brolio. To return to Gaiole, you have 2 options; downhill and flat, or challenging uphill to Castagnoli and downhill to Castello di Meleto. Tonight, you deserve a Michelin starred dinner at your hotel restaurant Il Pievano.
Lodging at the charming Hotel Castello di Spaltenna.

DAY 7: Badia a Coltibuono
Short loop Ride in Gaiole. Distance: 20 Km
If you still have energy and your legs feel strong, you can have a short ride to Badia a Coltibuono and back to Gaiole where you will leave the bikes.
Departure: Bus available to reach Siena where you can take a fast train to other towns.


Cost: € 1490 p/person

Tour name: Strade Bianche
Tour type: Self Guided Cycling Tour
Price based on double accommodation, it can change according to the period
Single occupancy: 350 €
Duration: 7 days/ 6 nights
Difficulty : easy going to moderate OR moderate to challenging; 2 options each day


  • Six nights in excellent four three-star superior hotels
  • Six breakfasts
  • Bike delivery in Pienza and professional bike fitting
  • Route notes, maps, elevation gain and city map
  • Sightseeing, restaurant and shopping suggestions
  • All Baggage transfers
  • Drop Off bike and gear in Gaiole
  • Keepsake BTS water bottle
  • All tax and service charges

Not included:

  • City tax: each village charge a tax per each day between euro 0,70 to 2,50 this can be paid only in cash to hotel for local administration
  • Bike Rental: Gravel or E-bike euro 210 p/week.


Begin: Pienza
End: Gaiole in Chianti





Day 1 & 2 Relais Il Chiostro di Pienza

Il Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool. View hotel website>>

Day 3 Si Montalcino

Hotel SI Montalcino is small charming hotel completely renovated, located on the panoramic road to S.Angelo in Colle, one km away from the walls of Montalcino. It is on a natural terrace that dominates the valley overlooking Monte Amiata and from here you can admire the vineyards of Brunello. Pool Belvedere View hotel website>>