Welcome To Italy
Dust In
The Wind
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.
Discover
The Place
From the rolling hills and cypress-lined roads of Tuscany,
this 10 day guided gravel cycling tour offers an authentic
experience of Italian landscapes, culture, and cuisine.
Between Gaiole in Chianti, Brolio Castle, Siena, Murlo, Pienza,
and Montalcino, riders explore scenic routes, historic villages,
and the iconic Strade Bianche, while enjoying local wines and
traditional dishes. The fully supported small-group tour includes
cultural visits, wine tastings, and unique experiences such as a
pasta cooking class, making each day special.
Route Information
Duration: 10 days | 8 cycling days
Tuscany
Start location: Gaiole Chianti
Middle location: Murlo
End location: Val D'orcia
Difficulty: Moderato
Schedule & Pricing
Total distance: 611 KM | 376 MI
Total elevation: 10593 M | 34743 FT
Dates: September 17/27 2026
Price: 3450€
Single occupancy: + 80 € for night
What's included
Discover the tour
day by day
Day 01
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 02
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 03
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 04
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 05
Transfer to Val D’Orcia
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 06
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 FT 4799
Day 07
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 08
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 09
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
Goodbye
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.
What's included
9 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.
Recommended Airports
Arrival/Departure: Roma
Photogallery
Explore The
Best Paradises
We’re constantly creating exciting new cycling tours, and here you’ll find some of our latest trips that explore our favorite up-and-coming destinations across stunning Italy.
Booking Trip
Controvento
Bike Hire
Scott Addict
30
Scott Addict
e-RIDE 30
Scott Solace
Gravel e-RIDE 30
Official clothing
Controvento
Your Trip
Starts Here
Contact us to plan your next cycling tour or
hiking adventure and experience Italy like never before.
We’ll take care of creating a tailor made experience
for you, through breathtaking landscapes, authentic
villages, and unforgettable adventures, designed for fun,
relaxation, and discovering the very best of our country.
