Tuscany Gravel Bike Tour | Eroic “Strade Bianche” | Self Guided

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Tuscany Gravel Bike Tour

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.

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Tour Details
Tour name Eroic “Strade Bianche”
Type of tour Self guided, Gravel cycling
Duration 6 nights, 7 days
Period From April to November
Level Moderate to Challenge
Total Distance 275km / 170mi
Daily mileage 45 to 55km / 28 to 35mi
Start Pienza (Sena province)
End Gaiole in Chianti (Siena Province)
Suggested Airports Rome or Florence


  • 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.
  • Treat yourself with Caffé espresso, cappuccino & the best gelato!
Not Included
Optional Services
  • 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
  • City Tax; each village charge a tax per each day between euro 0,70 to 2,50
  • Bike Rental
  • Pre/Post Additional Nights
  • Transfers to/from other destinations on the Island
  • Cooking lessons
  • Wine tasting

Day 1Welcome to Pienza & Bagno Vignoni. 25 km /15 miles Bike Test.

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
Meals included: welcome aperitif

Day 2 Loop from Pienza to Montepulciano & Vino Nobile. 51km / 31mi, Rolling hills.

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.
Meals included: Breakfast

Day 3Pienza to Montalcino, Brunello Wine. 41km / 25mi, hilly.

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
Meals included: Breakfast

Day 4 Montalcino to Siena. 56km / 35mi, Rolling hills.

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
Meals included: Breakfast

Day 5Siena to Gaiole in Chianti, the Eroica Town. 46km / 28mi, Rolling hills to Hilly.

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
Meals included: Breakfast

Day 6Loop from Gaiole to Castellina on Chianti Hills. 54km / 33 mi, rolling hills to Hilly.

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.
Meals included: Breakfast

Day 7Arrivederci! Good bye! Or short loop in Gaiole. Distance: 20 to 40Km.

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.


Self Guided
Tour Price: 1590€

Price based on double accommodation, it can change according to the period.

Make it custom: contact us for a quote!

Single occupancy: 560 €
Solo traveler: 880 €

Private & Custom departures at any time

Bike Rental: (price/week)
Touring Bike  € 140
Gravel Bike  € 210
E-bike € 210
Il-Chiostro bike hotel Pienza
Day 1 & 2  – Il Chiostro Relais, 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.

Giglio hotel Montalcino
Day 3 – Giglio Hotel, Montalcino

A charming retreat in the heart of town, hotel Giglio, family-run, in a warm and quiet building, facing a gorgeous landscape, the best part is the view of the cliff-clinging houses of Montalcino to your left and the rumpled patchwork of green valleys stretching out below.

villa str siena
Day 4 – Villa STR, Siena

Villa STR is a converted 19th-century villa that retains the charm and ambiance of its former origins as a private residence. The decoration in the recently renovated public areas bears the hallmarks of Italian classical design. It is just outside the ancient walls of the historic center of Siena, 

Castello di Spaltenna Bike tour
Day 5 & 6 – Castello di Spaltenna, Gaiole in Chianti

It offers an exclusive atmosphere amidst a unique landscape. Located in the heart of the Chianti Classico wine region, the manor’s luxurious guestrooms offer any possible comfort along with wonderful views over the valley. 


I contacted mauro to organize a tour for my dad and his girlfriend. They are experienced riders and have taken bike tour all around europe, but don’t speak english or italian.
Mauro helped me organize a tour specially for them, with cooking classes, wine tastings and other activities in spanish.
They had an amazing time, the hotels were beautiful, the food was delicious, and mauro took care of them all the time.

Paula, Colombia
June 1st , 2018