Strade Bianche 2026: discover Tuscany through its most iconic cycling race
Strade Bianche 2026 invites travelers to experience Tuscany in one of its most captivating moments...
This short cycling holiday invites you to experience the very best of southern Tuscany at a relaxed, enjoyable pace. Starting from the medieval city of Siena, you’ll spend three unforgettable days riding through some of the region’s most iconic landscapes—an ideal introduction for anyone dreaming of their first cycling adventure in Tuscany.
Your journey begins by leaving Siena behind and pedaling toward the rolling hills that lead to Montalcino, home of the world‑famous Brunello wine. The route winds through vineyards, cypress‑lined roads, and quiet country lanes, offering continuous views over the Val d’Orcia, a UNESCO World Heritage landscape celebrated for its harmony and timeless beauty. Each climb rewards you with sweeping panoramas, while each descent brings you deeper into the heart of Tuscany’s rural charm.
From Montalcino, the tour continues across the soft clay hills of the Crete Senesi, one of the most distinctive and photogenic areas of the region. Here, the scenery shifts into a lunar‑like landscape of gentle ridges, isolated farmhouses, and wide horizons. You’ll follow stretches of the historic Via Lauretana, an ancient pilgrimage route that connects Siena with the southern valleys, adding a touch of cultural heritage to your ride.
Across all three days, the itinerary blends scenic cycling with authentic Tuscan atmosphere: hilltop villages, medieval hamlets, traditional food, and the warm hospitality that defines this part of Italy. Designed for riders seeking a manageable yet rewarding experience, this tour offers the perfect balance of adventure and accessibility—ideal for those taking their first steps into multi‑day cycling in Tuscany.
A compact journey rich in landscapes, history, and emotion, this bike tour captures the essence of Tuscany in just a few days, leaving you with memories—and views—you’ll carry long after the ride ends.
5 days/4 nights
163 km - 101 mi
from € 730,00
Difficult: medium/high
Individual arrival in Siena, dinner on your own and accommodation in 3 stars hotel. Hotel 4 stars available on request with extra charge. Meet and greet with our staff, briefing where we’ll explain the bike tour.
You will leave Siena behind, cycling surrounded by the landscapes of the Val d’Arbia up to the small village of Ville di Corsano.
You will cross the route of L’Eroica, passing through Murlo, a small characteristic village. Downhill direction Buonconvento, one of the most beautiful villages in Italy and perfect for a quick stop or have lunch in one of the restaurants in the center.
Final part of the stage climbing up to Montalcino, a medieval town surrounded by fine vineyards and land of Brunello di Montalcino wine. Stop in one of the wineries along the way to taste good wine.
The alternative route along the route of L’Eroica will allow you to ride on gravel roads in the first part of the stage, passing through the typical countryside of the Val d’Arbia.
Dinner on your own and accommodation in 3 stars hotel located in Montalcino.
This stage will take you to discover two UNESCO sites: the Val d’Orcia and the city center of Pienza.
The Abbey of Sant’Antimo, one of the most beautiful Romanesque churches in Tuscany.
Bagno Vignoni, cute medieval town where the main square of the village is a big thermal pool which contains the original source of thermal water.
San Quirico d’Orcia, one of the most representative villages of the Val d’Orcia, with the town center full of bars, restaurants and small shops.
The views of the Val d’Orcia, one of the most evocative places in all Tuscany and UNESCO World Heritage Site. Before Pienza you can admire on the right the famous Vitaleta Chapel, one of the most photographed churches in Tuscany.
Visit of Pienza, the “ideal” city of the Renaissance, also famous for its pecorino cheese. Enjoy a walk in the town center before dinner and look out on the panoramic terrace from which you can admire the entire Val d’Orcia.
Dinner on your own and accommodation in 4 stars hotel located in Pienza.
An unforgettable ride surrounded by the beautiful views of the Crete Senesi to the edge of Chianti wine region.
After a few kilometers you can visit the monastery of Sant’Anna in Camprena, also famous for the movie “The English Patient”.
Crete Senesi, where Calanchi and biancane alternate in this suggestive territory. Castelmuzio and Montisi, small villages out of the most know tourist places.
Passage from San Giovanni d’Asso, the center of the white truffle of the Crete Senesi.
For the photography lovers, you’ll ride very slow this segment…The Via Lauretana offer unique landscapes and you’ll stop many times to take photos.
Dinner on your own and accommodation in 3 stars hotel located in Siena.
Hotel 4 stars available on request with extra charge.
Check-out and individual departure.
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