Welcome to the picturesque Chianti region, a perfect place to be introduced to Tuscany. Ride out to the quaint and charming villages of the region. In Greve, discover the architectural history and extrordinary Italian food & wines that make this region so unique. Gaiole offers a preview of what were the battles for local power that dominated these lands for over a hundred years. 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. This experience will allow you to fully immerse yourself in the beautiful Tuscan region of Italy.
The tour takes you to luxurious hotels across the Tuscan region. The first two nights are at the Realis Il Vignale in Radda in Chianti with a panoramic terrace overlooking the Chianti Hills. The Restaurant is an authentic example of culinary excellence, paired with their local wines. The next hotel, Certosa di Maggiano is loacted just outside of Siena. Enjoy wonderful hospitality and relax on the terrace overlooking the Chianti hills. Osteria dell Orcia is the final hotel for the tour in Bagno Vignoni it is situated in the UNESCO countryside, Val d’Orcia and is a 16th Century, historic building.
Dine out each evening at local restaurants and at your hotel on the more challenging ride days. The team will ensure you get to see and taste the best parts of the region. Each restuarant offers something different & our selection is designed to showcase the best food in the region. Lunches are served by your guide team in scenic locations along each route and feature healthy, fresh, seasonal produce designed to keep you riding all week.
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.
Welcome to the picturesque Chianti region. After checking in and meeting the team, head out on a short warm up ride to ensure everything is running smoothly for the week ahead. Enjoy a warm welcome evening meal tonight hosted by the hotel’s excellent chef.
Ride out to the quaint and charming village of Greve and discover the architetural history and extrordinary Italian food & wines that make this region so unique. as well enjoying a small tast of the Tuscan gravel roads. Have lunch in the village of Volpaia, a fortified village with hidden wine cellars. In the afternoon we’ll shuttle to a local vinyeard to enjoy a touch of wine tasting. Dinner tonight is at one of our favoruite places in the village.
Today we pack up and start our joruney south towards Siena. Our ride passes by the stunning vineyards and villages to the stunning Certosa di Maggiano just outside of Siena.
Today is a chance for a shorter ride, with time to explore Siena or relax at the hotel in the afternoon.
Our 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. Celebrate tonight with a farwell evening meal.
Sadly, the tour has come to a close. Let us know your departure plans and we will organise any necessary transfers for you.
FULL SUPPORT
Enjoy full ride support from our professional guide team & support vehicle.
The ride support vehicle is stocked with natural ride nutrition, electrolytes and water, as well as a full set of tools to resolve any mechanicals. On selected days the support crew will serve a delicious picnic lunch in a scenic location en route. Enjoy local foods chosen to keep you feeling energized and healthy.
Eat Sleep Cycle guides are experienced riders from all walks of life united by a love of cycling who’ll help to keep the group safe, motivated and savouring the trip of a lifetime.
All guests will receive access to our digital Road Book and routes, giving everyone the flexibility to ride at their own pace.
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 €40 per day
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!
Italia! Pizza! Pasta! The Giro! Italy is a classic destination for cycling holidays, with a huge variety of landscapes to explore & a history steeped in cycling culture. Italy is best enjoyed from April through to June and in the Autumn months.
Italy cycling tours offer something special for every cyclist. Whether you're looking for mountain ranges, excellent food or to ride around the lakes, our cycling holidays in Italy have you covered.
From the high mountains of the Alps and Dolomites in the North, to the Italian Lakes of Lombardia & Piemonte, to the rolling hills of Tuscany and Emilia Romagna, and off-shore to the islands of Siciliy & Sardinia, Italy promises to wow!
If you have any questions about our tours, dates, or anything else, contact us here
