Tuscany is a special land, an open-air museum like nowhere else in the world, full of art cities, medieval towns and perfect landscape characterized by rolling hills and cypress trees . In fact, UNESCO has declared seven places in Tuscany as World Heritage Sites, four in the province of Siena.
This cycling tour will lead you to biking in the most attractive areas and discover the four UNESCO sites in the province of Siena: the city center of Siena, the Val d’Orcia region, the town center of Pienza and San Gimignano.
Individual arrival in Siena, dinner on your own and accommodation in 3 stars hotel or hotel/residence with swimming pool. 4 stars hotel available on request with extra price.
During your stay in Siena you can visit the first UNESCO site: the city center of Siena.
Meet and greet with our staff, briefing where we’ll explain the bike tour.
55 km – Elevation gain: 1080 meters
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 a 3 stars hotel located in the city center of Montalcino.
48 km – Elevation gain: 1040 meters
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 at Pienza.
60 km – Elevation gain: 1160 meters
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. Hotel 4 stars available on request with extra charge.
58 km – Elevation gain: 1020 meters
Villa a Sesta, little jewel in Chianti region. – The Castle of Brolio, symbol of Chianti and excellent wines to taste. Before to follow the road to Gaiole in Chianti, you will have the opportunity to visit the Castello di Brolio, dating back to the 11th century and owned by the Ricasoli family since 1141. – Radda in Chianti, small medieval village full of tiny streets and beautiful view over the vineyards. Radda is a great place to stop for lunch and enjoy the atmosphere of this medieval town.
Final arrival in Castellina in Chianti, one of the most important towns in the Chianti region.
Dinner on your own and accommodation in 4 stars hotel.
50 km – Elevation gain: 680 meters
San Donato in Poggio and Tavarnelle, discovering the hills covered by vineyards and olive groves. – Certaldo, the magical village of Boccaccio. You can make a small deviation to the route and reach Certaldo Alta, where the oldest part of the town is located. – Climbing up to San Gimignano, the famous medieval village with beautiful towers. The road that will take you to San Gimignano will be a sequence of breathtaking views of the surrounding hills and the towers of San Gimignano. – Thanks to the strategic position of the hotel, located in the main square of San Gimignano, you will have the opportunity to visit the last UNESCO site of this trip: the city center of San Gimignano.
Dinner on your own and accommodation in 3 stars hotel.
4 stars hotel available on request with extra price.
49 km – Elevation gain: 680 meters
With a long descent you will leave the towers of San Gimignano behind. – Colle Val d’Elsa, the city of crystal. The route will lead you across the old town. – Abbadia Isola, a Benedictine monastery founded at the beginning of the year 1000. – Monteriggioni, to discover one of the best preserved medieval villages, with the walls surrounding the town.
You’ll be back to Siena passing through the Montagnola Senese, typical area surrounded by woods.
Dinner on your own and accommodation in 3 stars hotel or hotel/residence with swimming pool. 4 stars hotel available on request with extra price.
Check out and individual departure after breakfast.
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