Adventure Unpaved & Escape the Crowds

Val d’Orcia to Siena on gravel road

Most people choose to ride gravel to escape traffic and get off the beaten roads, exploring the hill town tahta made Tuscany so famous.  The amount of pavement varies from destination to destination, but one thing holds true, once you are on gravel, you’ll encounter minimal traffic.

This is a short escape – 4 nights in case you do not have entire week or you want  just to test gravel bikingmin the legendary white roads


Gravel Tuscany Bike tour’s 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.



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 /15 miles
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 52 km /31 miles : 17 km asphalt and 34 km gravel - moderate difficulty

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 dinner is included so you can reward yourself at least a glass of Brunello - we have a list of our favorite.
distance 41 km /25 miles
17 km asphalt and 24 km gravel - moderate difficulty

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 56 km /35 miles
32 km asphalt and 24 km gravel - moderate to challenge


End of Tour after Breakfast
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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.

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
Hotel Giglio - 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. Plus a great restaurant where enjoy gourmet tuscan dinner
Vecchia Oliviera - Montalcino
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

gravel bike tour map

Price & Inclusions

Cost: Euro 1090 per person – Price based on double accommodations

single room supplement euro 300

Four nights in excellent five, four & three-star superior hotels
Four 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 Siena
Keepsake Cicloposse water bottle
Sales taxes

Not Included
Bike Rental per entire tour

GRAVEL OR E-Bike         euro 140


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