Soak up the Tuscan sunshine at your own pace on our self-guide tour of Tuscany! Start the journey in the Chianti wine region and explore the quaint & charming villages. In Greve, discover the architectural history and extrordinary Italian food & wines that make this region so unique. Pedal through the stunning vineyards and villages of Castelnuovo Berardenga as well as the UNESCO Siena hills. You’ll ride the “Crete Senesi” and a section of “Le Strade Bianche” passing through Asciano and San Giovanni D’Asso. Stay in wonderful hotels throughout the trip and fully immerse yourself in the beautiful Tuscan region of Italy!
Rated 2 out of 4 our Intermediate tours are designed for sporty people who are looking to enjoy some more challenging rides. E-bikes are available on all of our tours.
We’ll collect you in Florence and drive you to the picturesque Chianti region! After checking in we’ll brief you about the ride ahead & ensure you have everything you need to enjoy the ride! Head out on a short warm up ride to ensure everything is running smoothly for the week ahead.
Ride out to the quaint and charming village of Greve and discover the architectural history and extraordinary Italian food & wines that make this region so unique. as well enjoying a small taste of the Tuscan gravel roads. Stop for lunch in the village of Volpaia, a fortified village with hidden wine cellars.
Today pack up and ride south to Siena. Our ride passes by the stunning vineyards and villages to the stunning Certosa di Maggiano just outside of Siena. Visit Siena in the afternoon or relax in the grounds of the hotel.
The final point to point ride is to Bagno Vignoni. The UNESCO Siena hills and the countryside make this ride truely spectacular. You’ll ride the “Crete Senesi” and a section of “Le Strade Bianche” passing through Asciano and San Giovanni D’Asso. Have lunch in San Quirico then bike to your final accommodation, the wonderful Osteria dell Orcia in Bagno Vignoni.
The final ride of the tour will take you to Pienza, a UNESCO site and very famous for the Pecorino cheese.
Sadly, the tour has come to a close. A transfer back to Florence is included in the tour.
SELF-GUIDED
We’ll welcome you to the start of your tour, talk you through the week ahead and ensure you have everything you need to enjoy a great ride.
Guests receive a detailed digital Road Book, containing routes, route descriptions, details of hotels and our recommended places to stop along the way and enjoy in the evenings. Guests can choose to navigate from their own phone or GPS devices are available on request.
On a self-guided tour we take care of your luggage and move it from hotel to hotel. We also provide a contact number for support during the trip and will help you out of any situation.
We recommend that guests are able to fix a puncture and perform basic roadside bike repairs to best enjoy a self-guided tour.
Hotels shown are examples and are subject to change
The perfect balance between prevailing silence and peacefulness. At the Relai Il Vignale you can truly relax in the spa, pool or lay down in the large flower-filled garden, featuring a panoramic terrace overlooking the Chianti Hills. The Restaurant is an authentic example of culinary excellence, paired with their local wines.
A wounderful 4* boutique hotel hidden in the Tuscan countryside.
Situated in the UNESCO countryside, Val d’Orcia is a 16th Century, historic building. The hotel will give you a Tuscan experience with its traditional food & Tuscan wine. Book a massage and embrace the green oasis.
Bike hire is not included in the tour. Add bike rental to the trip from €60 per day.Bikes shown here are examples and are subject to availabilty at the time of booking. We'll let you know the available options in your size when you book with us.
The best all-rounder for long-distance comfort, the Basso Astra as a Campagnolo 12spd Wireless Groupset (48-32 || 10-29) and a Microtech RE38 Wheelset
The ulitmate Italian climbing bike from Basso. Equipped with Campagnolo 12spd Wireless Groupset (48-32 || 10-29) and Campagnolo WTO Wheelset
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 ESC Team since 2019 and couldn’t be happier! He looks forward to seeing you on the road soon!
Our cycling holidays in Italy offer a unique way to explore the country’s varied landscapes and rich heritage. From steep climbs of the Dolomites and Alps to cruising through Tuscany and the coastlines of Sardinia, there’s something for every rider at every level. Whether you're drawn to quiet country roads, challenging mountain passes, or lakeside routes, Italy combines great cycling with incredible food, local wine and a deep cycling culture. An Italian cycling holiday is the perfect blend of adventure and discovery, best enjoyed in spring or autumn. Discover our tours today.
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