DUST IN THE WIND

Experience the ultimate classic cycling in Tuscany, world famous for its Strade Bianche
(White Roads), breathtaking and uninterrupted cypress-lined horizons, gastronomical delights and delicious red Chianti or Brunello di Montalcino wines.
This gravel adventure promises an unforgettable experience that will leave you longing for more.
Be a part of a small group of likeminded cyclists in this fully supported and guided tour and discover the magic of Tuscany on two wheels 

TUSCANY
DIFFICULTY | MODERATO
MIDDLE LOCATION | GAIOLE IN CHIANTI
END LOCATION | VAL D'ORCIA

DURATION | 10 DAYS / 8 CYCLING DAYS
TOTAL DISTANCE | 611KM / 376MI
TOTAL ELEVATION | 10593M / 34743FT
DATES | MAY 10/19 2025
PRICE | 3450 EURO
SINGLE OCCUPANCY | 70 EURO

DUST IN THE WIND

Experience the epitome of classic cycling in Tuscany, renowned for its iconic Strade Bianche (White Roads). 

Immerse yourself in breathtaking and uninterrupted views of cypress-lined horizons, savor gastronomic delights, and indulge in delectable red Chianti or Brunello di Montalcino wines.

This gravel adventure promises an unforgettable experience that will leave you yearning for more. Join a small group of like-minded cyclists on this fully supported and guided tour and embark on a journey to discover the enchanting magic of Tuscany on two wheels. 

OVERVIEW
Day 1 Sat Transfer to Gaiole in Chianti and Welcome
Day 2 Sun ChiantiShire
Day 3 Mon Brolio Castle
Day 4 Tue Magical Siena (culturale visit after ride)
Day 5 Wed Transfer by Bike to Murlo
Day 6 Thu Pienza Loop
Day 7 Fri Montalcino / Wine Tasting
Day 8 Sat Monte Sante Marie (pasta cooking Class)
Day 9 Sun Cipressi
Day 10 Mon Transfer to Airport

WHAT’S INCLUDED

11 nights luxe accommodation (twin share) | breakfasts | lunches | dinners | guides and vehicle support | mechanical support | on-road snacks and supplements | daypack | bidons | laundry service for cycling kit | group airport transfers

WHAT’S NOT INCLUDED

Flights | insurances | bike hire | alcoholic beverages | coffee stops | personal hotel expenses.

AIRPORT: Roma 

Dust in thw wind

FULL ITINERARY

DAY 1

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Day 1 | Saturday 
Transfer & Welcome

Gaiole in Chianti is a charming municipality located in the Chianti region of Tuscany, known for its scenic beauty, vineyards and winemaking tradition. The Chianti area is world famous for the production of Chianti wine, one of Italy's most celebrated red wines. This region is characterised by rolling hills, medieval villages, and a rich food and wine culture. Chianti wine is a blend based on Sangiovese, which must make up at least 70% of the wine. It is known for its fruity flavours, spicy notes and good acidity, making it suitable to accompany a variety of dishes, from pasta to meat. The Chianti region is divided into several sub-zones, including Chianti Classico, which represents the historical and qualitative heart of production.

DAY 2

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DAY 2 | ChiantiShire 

L'Eroica is a cycling event held annually in Gaiole in Chianti, established in 1997. L'Eroica is distinguished by its vintage spirit, as participants use vintage bicycles and wear historical clothing. The race takes place on white roads, a type of dirt road typical of Tuscany, which makes the experience unique and fascinating. L'Eroica promotes the beauty of hard work and the taste of enterprise. It is not a race in the competitive sense, but a journey through time, discovering Tuscany and the cycling traditions of the past.

Km 75 Mi 46 Mt 1420 Ft 4660    

DAY 3

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DAY 3 | Brolio Castle

A fascinating castle, rich in history, an important name for Chianti wine production
A road through vineyards and farmhouses, dust and unique views
A day that will remain forever in our hearts and minds

DAY 4

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DAY 4 | Magical Siena

Siena and its contrade, famous for the fierce battle that twice a year contends for the famous Palio
What can we say about a magical city that we don't know? Certainly the fact of cycling through it on the streets of the famous Strade Bianche professional competition

Km 82 Mi 51 Mt 1350 Ft 4430

DAY 5

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Day 5 Wednesday
Transfer to Val D’Orcia
Bosco alla Spina Resort - Murlo

The Val d'Orcia is one of Tuscany's most iconic and evocative regions, characterised by breathtaking landscapes, rolling hills, lonely cypresses and historic villages. Cycling through the Val d'Orcia is an unforgettable experience that allows you to immerse yourself in the natural beauty and rich culture of this area. Murlo has a fascinating history dating back to Etruscan times. This territory was an important Etruscan centre, as shown by the numerous archaeological finds in the area. During the Middle Ages, Murlo was a fief of the bishop of Siena, who maintained control over this land until the 19th century. This link with Siena greatly influenced the architecture and culture of the village.

DAY 6

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DAY 6 | Pienza Loop

The Crete Senesi are characterised by clay hills and calcareous soils, which create a unique and fascinating lunar landscape. This area, south-east of Siena, offers spectacular views, especially at sunset, when the hills are tinged with warm hues.
Pienza is known as the 'ideal city' of the Renaissance, thanks to the urban planning vision of Pope Pius II and the work of architect Bernardo Rossellino. The town is a jewel of architecture and offers a romantic atmosphere with its narrow streets and panoramic views over the Val d'Orcia.

Km 84 Mi 52 Mt 1463 Ft4799

DAY 7

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DAY 7 | Montalcino Loop

Montalcino is a picturesque hilltop town in the province of Siena, Tuscany, famous worldwide for its fine wine, Brunello di Montalcino. In addition to its famous wine, Montalcino also boasts a fascinating medieval history, visible in its ancient fortifications and impressive castle.  Brunello di Montalcino is one of Italy's most prestigious red wines, made from 100% Sangiovese grapes. The production of this wine dates back to the mid-19th century, when Clemente Santi began experimenting with innovative winemaking techniques.

Km 69 Mi 43 Mt 1160 Ft 3800

DAY 8

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DAY 8 | Monte Sante Marie

Monte Sante Marie, located in the municipality of Asciano in the Crete Senesi, is one of the most iconic and fascinating sections of the famous Strade Bianche cycling race. This race is distinguished by its unique route that includes several sections of dirt roads, typical of the Tuscan countryside.  Is one of the most difficult of the Strade Bianche, known for its challenging gradients and the length of the gravel section.

Km 82 Mi 50 Mt 1430 Ft 4690

DAY 9

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DAY 9 | SUNDAY | Cipressi

Cypress trees are a distinctive element of the Tuscan landscape and of the Val d'Orcia in particular. These slender, evergreen trees dot the hillsides, often lined along the avenues leading to farmhouses and villas or isolated in groups that stand out in the undulating landscape.

Symbols of Eternity: Cypresses are often associated with eternity and continuity, due to their longevity and majestic form. - Landmarks: Used to mark boundaries and paths, cypress trees are often planted along roads and property access roads, creating a scenic effect that attracts visitors and photographers from all over the world.

DAY 10

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DAY 10 |Goodbye/Arrivederci/Auf Wiedersehenodbye

After breakfast and check out we leave as a group for the airport to catch an afternoon flight back, or continue your stay in Italy. Taking back home all the wonderful memories with us. We hope you loved this trip and already thinking of your next cycling adventure with Controvento. 

DISCOVER ALL TOURS

An opportunity to discover by bike the cycling and culinary culture of the most desirable and iconic Italian destinations.

DISCOVER ALL TOURS

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