Recreational cycling holidays in Tuscany

Guided Road/Mountain bike holidays in the stunning areas of Val d’Orcia and Val di Chiana.

Cycling Tuscany offers interesting guided holidays suitable for singles, couples and small groups where you will discover an area rich in flavours and history, tucked away in the south eastern corner of Tuscany.

You will have the opportunity of visiting the historic town of Montepulciano which stands dominantly along a ridge, and is said to be one of the highest hilltop towns in Tuscany in the area of the renowned Nobile wine production. The views from there are breathtaking, one of which takes your eye across to another ridge with the medieval hilltop village of Montefollonico, believed to be the birthplace of the dessert wine Vin Santo and a place which gives the illusion of time having stood still.

Derek at Pienza

Derek at Pienza

Also on the menu is a stop at the renaissance small town of Pienza which overlooks the UNESCO national heritage park of the Val d’Orcia famous for its sheeps cheese production overlooked by the dormant volcano Monte Amiata. The landscape is very particular and one which is not to be missed, the Crete Senesei stretches from San Quirico d’Orcia all the way to Siena. When booking your holiday with us, you’ll be able to choose either a hybrid, mountain bike, road bike or an ebike (electric motor assisted) cycle depending on the holiday chosen. You’ll join an experienced cycle guide who knows this area very well and you’ll be able to cycle on quiet picturesque routes.



Ideal cycling conditions for leisure cyclists who wish to calmly ride through this beautiful region at a leisurely pace, as well as those who like to ride more briskly. All our daily routes are customised to the abilities of the participants, ensuring that everyone has an enjoyable experience.

We are an enthusiastic team with great knowledge of this area. You’ll ride with Derek, an experienced English cycle guide, who will take you on fabulous routes and you’ll meet his colleague Luca who grew up in this area and has a great passion for the culture and environment. Just some of the benefits when you come with us –

  • Personal attention from Derek and Luca
  • Choice of bike style, on booking
  • Airport transfers to and from hotel
  • 4 Days of guided cycling along picturesque routes
  • Friendly and comfortable hotel in a small lively spa town

Choice of bike style

For more information on our holidays, please visit Cycling Tuscany and you can contact Derek directly at [email protected] or you can call on 0039 348 906 8394.

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Mother of three grown-up daughters I am the ultimate multi-tasker and am passionate about my role as Silversurfers Website Editor and Social Media Manager. Always on the lookout for all things that will interest and entertain our community. Fueling fun for the young at heart!

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13th Aug 2017
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I am looking forward to being a member of Silversurfer's, I think I would very much like to cycle in Tuscany with a group of other people and perhaps pick up some of the lovely Italian language.

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