Tuscany: Eroica & Val D'Orcia bike tour

Tuscany: Eroica & Val D'Orcia bike tour

May 29th - June 4th, 2022 or upon request
Difficulty level: intermediate


Why choosing this holiday:
  • Live a true gravel experience on Tuscany most iconic routes 
  • A triumphant arrival at Siena Piazza del Campo 
  • Try hand made Pici, Fiorentina Steak and enjoy Brunello di Montalcino wine


L'Eroica is one of the most iconic events in world of cycling. This six days holiday will take you pedalling on Eroica route, while experiencing Tuscany at its best: its picturesque villages and landscapes, the Sienese hills, the enchanting Val D'Orcia and its views, marked by lines of cypresses. How about a break from the fatigue and dust of the dirt road, relaxing in a spa and enjoying the fantastic food and wines of this unique land? History, art, special cuisine, great cycling and fun are what makes this area of Italy famous all over the world. Experience Tuscany’s passion for gravel and follow the tracks of this country cycling icons.


Day 1 | Arrival in Siena

Welcome to the hotel and briefing. After the presentation of the staff, we will check together the equipment and positioning on the bike. 

Accommodation: La Certosa di Maggiano 


Day 2 | Siena - Buonconvento

55 km, 710 m 

On our fist day we are going to have an easy ride. Descending from Siena and riding right on Strade Bianche route, a mixed terrain that will take us trough the classic Tuscany clay hills across its beautiful sunflowers and wheat fields all the way to Buonconvento.

Accommodation: Villa Armena


Day 3 | Buonconvento - San Quirico 

47 km, 1100 m 

Buonconvento San Quirico. Yes, we all have in mind those postcard-like dirt roads running between lines cypresses of Tuscany surrounded by wineyards producing one of the most famous wine Binello di Montalcino. We will be right on the Eroica and Giro d’Italia most incredible stages. Add the epic winding road, set of Millemiglia historic car race, arriving at San Quirico d’Orcia and you will live the true spirit of Italy’s most famous countryside.

Accommodation: Palazzo del Capitano


Day 4 | San Quirico - Montepulciano - San Quirico

44 km, 900 m 

Today we will continue pedaling through Val d’Orcia UNESCO site, heading to Pienza, one of the most stunning artists sets, like the photographer Franco Fontana, and continuing on a mixed terrain to the beautiful middle age village of Montepulciano, with its square overlooked by Pulcinella Tower (popular Italian folklore character) and famous for his Nobile red wine. The beautiful winding roads of Tuscany will take us back to San Quirco.

Accommodation: Palazzo del Capitano


Day 5 | San Quirico - Spa and Wine Tour 

0 km, 0 m 

The day will be dedicated to enjoining best Tuscany thermal waters spa and discovering some of its most famous wines visiting local wineries. Leaving by van and safely returning to the hotel in the afternoon.

Accommodation: Palazzo del Capitano


Day 6 | San Quirico - Castelnuovo Berardengo - Siena

66 km, 1000 m 

We will descend from San Quirico to admire Tuscany’s roads dotted by cypresses and to cycle immersed in this beautiful hills, warming up our muscles for the climb to San Giovanni d’Asso. On the way to Asciano we will pass Baccoleno beautiful farmhouse, with its enchanting winding road. We will continue riding right in the heart of Chianti region, through its famous vineyards and passing Castelnuovo Berardenga. This wonderful week “grand finale” will be the arrival at Siena iconic Piazza del Campo, set of the world famous historical horse race, Palio di Siena. 

Accommodation: La Certosa di Maggiano 


Day 7 | Siena

This is your last chance to visit Siena and to have a glass of red wine or a Negroni. Goodbye Tuscany! 


Price per person (minimum 6 - maximum 12 px): 

EUR 3.200,00 (taxes and VAT included) | single supplement, applied to secure a private room for solo travellers: EUR 500,00 (taxes and VAT included)

USD 3.700,00 (taxes and VAT included) | single supplement, applied to secure a private room for solo travellers: USD 570,00 (taxes and VAT included)

This tour can be organized private for any number of participants. Contact us for details. 


The price includes

  • 6 nights in luxury accomodations in double room with breakfast | 6 dinners (3 hotel + 3 restaurant)  
  • Cycling guide | van and mechanic in tow for ordinary assistance (eat and drink) | photos and videos along the routes and during visits
  • All minivan transfers, bike and luggage transport | transfer from and to the airport
  • Welcome kit Vince Team supplement | 20% discount on Cinelli Bike apparel and accessories


The fee does not include

  • Flight
  • lunches | drinks with food  
  • Travel insurance

Anything not mentioned in "The price includes" 



  • Bike rental
  • Ital Cycling gives you the exclusive opportunity to ride and live for one or two days with a great cycling champion like Claudio Chiappucci, Alessandro Ballan and Valerio Agnoli. Upon request


Any questions? Read our FAQ.