Cycling Tour With Expert Support in Tuscany, Italy

7 Days, Multiple Departures

Cycling Tour With Expert Support in Tuscany, Italy
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Cycling through Tuscan Charm and History

Discover the picturesque Chianti region, your gateway to Tuscany's wonders. Cycle through quaint villages, from Greve with its rich architectural heritage and delectable Italian cuisine to Gaiole, where history echoes through ancient battles for local dominance. Traverse the stunning vineyards and villages of Castelnuovo Berardenga and the UNESCO-protected Siena hills. Pedal along the iconic "Crete Senesi" and a segment of "Le Strade Bianche," passing through Asciano and San Giovanni D'Asso. Immerse yourself in the beauty of Tuscany.

Indulge in luxurious accommodations throughout your journey. Begin at the Realis Il Vignale in Radda in Chianti, boasting panoramic views of the Chianti Hills and exquisite culinary offerings paired with local wines. Continue to Villa Curina in Castelnuovo Berardenga, nestled in a charming 16th-century village, offering delectable local fare and captivating vistas of the Chianti hills and Siena. Conclude your tour at Osteria dell Orcia in Bagno Vignoni, a historic 16th-century building set amidst the UNESCO-recognized Val d'Orcia countryside.

Experience authentic dining experiences each evening, sampling the region's finest cuisine both at local restaurants and your hotel on challenging ride days. Our carefully curated selection showcases the diverse flavors of the region. Enjoy scenic picnic lunches prepared by your guide team, featuring fresh, seasonal produce to fuel your cycling adventures.

About The Host


Emanuela is Italian and after many years living in Barcelona relocated to Mallorca. She started triathlon 10 years ago and has made it her life! Alongside guiding Emanuela hosts guests from all over the world in her Airbnb.


During the past 10 years, Mario has lived in different countries, but now he's back home in Conegliano to ride every steep hill in the area! Despite his focus on road cycling, he's had some amazing moments with his beloved steel gravel bike! Mario has been a member of the Team since 2019 and couldn't be happier! He looks forward to seeing you on the road soon!


Things to keep in mind