Gravel Cycling Strade Bianche

Gravel Cycling Strade Bianche

Gravel Cycling Strade Bianche

Tuscany - Self Guided

Strade Bianche Bike Tour

Val d’Orcia to Gaiole, the Eroica town The Famed White Roads of Tuscany
These white, dusted roads are home to one of pro racing’s biggest dates, with steep climbs and full-blown attacks at every bend.
The Strade Bianche of Tuscany is truly something special due to the region’s rolling vistas and fine wines make this a must-see destination if you love gravel cycling. Strade bianche  is Italian for “white roads,” and it comes from the color of the dry limestone gravel that lifts into a fine white dust that lingers along the race course


Wow Moments

  • Shadow the hilly path of L’Eroica, Tuscany’s internationally recognized vintage bike race.
  • ancient cellars, taste superb Tuscan wines, from Vino Nobile di Montepulciano to Brunello di Montalcino.
  • Experience the serenity of the Tuscan countryside and savour the flavours of authentic pasta fresca.
  • Explore the undulating white gravel roads of Tuscany—the famed strade bianche—and immerse your self in Italy’s most classic cycling local.
  • Caffé espresso, cappuccino & best gelato.

Discover the route of the Strade Bianche professional race. In this self guided Bike Tour  we selected the more appropriate unpaved sections from  the race and also from the Eroica itinerary. The Permanent Route of L’Eroica is a unique experience that allows you to live the adventure of L’Eroica all year round. Anyway we offer the tour from March to November. Traditional L’Eroica course  starts in the town of Gaiole and covers some of the most beautiful roads in the area of Chianti and Siena province,  winding among historic vineyards, leading to the cypress-lined entrance of Castello di Brolio and Corte Pavone. Quote from the Eroica home page  “L’Eroica invite cyclists to rediscover the beauty of fatigue and the thrill of conquest. We look to the past of cycling to inspire the future of this beautiful sport” 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



Pienza & Montefollonico

Meet & Greet in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets.
If you arrive in time there will be a First test bike ride to Palazzo Massaini, Montefollonico

Distance 25 km    +558 m / -565 m
12 km asphalt and 13 km gravel
Easy to Moderate


Montepulciano & Bagno Vignoni

Your tour starts with a circular 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. As we pedal through these corridors of proud cypress trees, the scenery may look familiar from such films as Gladiator and The English Patient. Follow the gravel tracks off the beaten path through a timeless slice of Tuscany. You’ll come to Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. After relaxing a while, you will face a incredible breathtaking yet challenge gravel section that bring you to Monticchiello, the quintessential Tuscan hill town.
back in the valley, next destination is Bagno Vignoni, a thermal spa town that dates back to Roman times, Madonna di Vita Leta chapel is on the way back to Pienza

Distance 51 km   +872 m / -875 m
17 km asphalt and 34 km gravel


Pieve a Salti to Brunello Land

To get from Pienza to Montalcino we select the sections of Eroica called Lucignano d’asso and Pieve A Salti. You leave Pienza and after 6 km on paved road you will take with white road toward Cosona and reach the little hamlet of Lucignano – a caffe espresso at little shop emporio – is a must. Once you reach the paved road you ride only one km and start the other Eroica gravel section Pieve a Salti – so beautiful landscape. 9 km up and down in the rural countryside! arrive in Buonconvento by lunch time. Now you have to face the climb to the famed wine town of Montalcino. A total of 10 km: 5 on paved and 5 km on gravel all through vineyards and wineries. Once in town we strongly suggest to visit the fortress and admire the breath-taking view of the entire valley you’ve just biked.
Tonight at dinner you can reward yourself at least a glass of Brunello – we have a list of our favorite.

Distance 41 km   +855 m / -807 m
17 km asphalt and 24 km gravel


Castiglion del Bosco & Siena

L’Eroica—meaning “The Heroic”—is a celebration of the golden age of cycling. The event 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 participant’s water bottles and the hardman mentality. Today, we’ll have our own taste of cycling’s heroic origins as we join one of the most beautiful gravel sections of L’Eroica. From the heart of Brunello di Montalcino, Tuscany’s most celebrated wine region, ride to the top Passo del Lume Spento. In fact starts the Castiglion del bosco gravel section. Castiglion del bosco is the biggest brunello winery & farm belonging to Ferragamo, the famous Italian fashion designer. Once in Bibbiano another section called la Piana and reach Murlo after 30 km- caffé & visit! Shortly you will face another legendary Eroica section to Radi, with some steep yet short up and down. At Ville di Corsano you deserve a light lunch. from here you have the last 12 km on secondary paved road to Siena.

distance 58 km   +1,015 m /-1,229 m
32 km asphalt and 24 km gravel


Gaiole, the Eroica town

Today the destination is the town where the Eroica starts.
After your gourmet breakfast, head out into magical Chianti. You will exit form Siena via a eroica gravel section Pieve a Bozzone, Vico d’Arbia making your way through wheat fields before we hit the vineyards of this celebrated wine region. Reach Pianella after 15 km. From here you will take a long glorious section to Canonica A Cerreto, Vagliagli. All riding through chianti classico vineyards, counting castles and old hilltop hamlets! Get in Radda in Chianti for lunch time after 38 km ride – mostly gravel.
relax .. you have only 8 km to Gaiole following still the Eroica itineray. Last gravel stage: San Donato in Perano and Vertine are amazing, enjoy the breathtakign landscape.

distance 46 km +923 m / -874 m
12 km asphalt and 34 km gravel


Chianti hills – Castello di Brolio

Today is consacrated to explore all the villages and hamlet of Chianti Senese. Start from your “castle di Spaltenna” in Gaiole and reach Castello di Brolio afer 10 km. Here the caffe at agribar in front of winery is a must: all cyclists, locals and visitors seems to meet there.
After you can ride into the gravel section of Eroica, is short and then you will ride on very secondary scenery roads until Castelnuvo Berardenga. It worth a visit and if you are there for lunch time offer many options. Back to the saddle and encounter other small borgo: San Gusmé and villa a Sesta. Back to Brolio: to return to Gaiole you have 2 options, one road downhill and flat so somewhat easy, or challenge uphill to Castagnoli, downhill to castello di Meleto.

distance 54 km   +1013 m / -1012 m
44 km  asphalt and 10 km gravel


Badia a Coltibuono short loop

If you still have energy and feel your legs stronger you can have a short ride to Badia a Coltibuono a loop of 20 km
Back to Gaiole where you will leave bikes.
Departure: bus available to reach Siena where you can take fast train to other town

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Cycling eroica path
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Eroica cyclists in Pienza
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gallery gravel 10 Gravel Cycling Strade Bianche
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Tour start in Pienza
Tour end in Gaiole

gravel bike tour tuscany map



best period : from end of March to end of October

DIFFICULTY : medium to challenge

TOTAL DISTANCE : 275 km/ 172 miles in 5 stages



Tour Reviews

2 September 2022

Hello Giuliana,

Rick and I just arrived back in the USA and wanted to take a moment to let you know that we had a wonderful Gravel Bike Trip. We thank you for the extraordinary job organizing, responding and planning the tour. The hotels were lovely and everyone was so helpful. Your Bike Trip Handbook was very helpful and will be a treasured souvenir from our trips. We will definitely look into taking another bike tour with your company and have already passed the word on to many of our friends and relatives. Maybe Sardinia! We do not have Instagram but will share our five star rating on sites listed.

It was great working with you and I wish you the best with your tours this Summer.

Thanks Again,

6 July 2022

Hi Giuliana,

We had such a wonderful week biking through Tuscany and were so pleased with you and your Cicloposse family. It was very enjoyable working with you and your company’s expertise allowed us to have a stress free week. We will certainly recommend you to everyone who inquires.

Thank you,

6 July 2022

Hello Giuliana

Thank you for arranging a very fun and successful trip for all of us. We loved every day of biking and it was really just what we needed. The accommodations were also excellent and so was the gear.
we had no problems at all, … thank you again for all your coordination. We will definitely let others know about Cicloposse and will be in touch again if we want to travel elsewhere through Italy, or to have you connect us with a “partner” company in a different country who does similar tour organizing.

Leave a Review


Cost: € 1690 per person – Price based on double accommodations
single room supplement € 560


Six nights in excellent five, four & three-star superior hotels
Six breakfasts
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Maps with elevation gain
Delivery bike at Pienza hotel & bike fitting
Pick-up of bikes and gear in Gaiole
Keepsake Cicloposse water bottle
Sales taxes

Not Included

Bike Rental per entire tour
Gravel bike, E-Bike         euro 250


il Chiostro – 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.

LUXURY UPGRADE – La Bandita Townhouse – Pienza

La Bandita Townhouse is a luxury boutique hotel tucked inside the historic center of Pienza. The building is a rambling Renaissance-era palazzo where nuns have lived for over 500 years. the property itself blends in completely with the Renaissance character, is a comfortable, and stylish place

Vecchia Oliviera – Montalcino

Vecchia Oliviera is located in the historic center of the city of Brunello and stands next to Porta Cerbaia, one of the six ancient gates to the city of Montalcino. an old oil mill restored and transformed into this charming hotel with garden overlooking Orcia valley

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, with a quiet Garden for relaxing . Hotel is a 10-minute walk from Piazza del Campo

Castello di Spaltenna – Gaiole in Chianti

Castello di Spaltenna 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. Just on hill out of Giaole in Chianti – few meters – restaurant Pievano

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