Self-guided Cycling / Original tour

Web code IT031

Italy / Tuscany

Siena, Chianti District and Florence

The landscape of Tuscany is one of the most beautiful and evocative in Europe, with rolling hills laced with verdant vineyards and cypress trees lining the roads. You will pedal from one incredible view to the next, getting to know the lands of many great artists of the past, such as Leonardo da Vinci and Michelangelo. You will have the chance to visit the superb medieval town of Siena, as well as to admire Florence, the cradle of Renaissance. Last but not least, in this tour you will discover also picturesque villages where you will be tempted by the excellent Tuscan cuisine.
  • Day by Day


    1. Siena
    Individual arrival.

    2. Siena – Radda in Chianti (45 km)
    From Siena head north towards the beautiful village of Radda in Chianti. The remains of its ancient walls show the  significance that this town had in the competition between Florence and Siena.
    3. Radda in Chianti – Greve (40 km)
    The route brings you to Greve over the rounded hills with beautiful views.

    4. Greve – Florence (40 km)
    You will cyle to Florence, capital of Tuscany, and admire the world famous artworks of Leonardo and Michelangelo.
    5. Florence – Tavarnelle (40 km)
    The village of Tavarnelle Val di Pesa has Roman origins; it is named after the ancient taverns offering accommodation and refreshment located along the road which linked Florence to Siena and thence to Rome.
    6. Tavarnelle – Colle Val d’Elsa (45 km)
    From Tavarnelle you cycle to Colle Val d’Elsa, which lies in the heart of Tuscany, in a strategically favourable position near the towns of Siena and Florence. It is situated on the via Francigena that connects Rome with the North. On the way you pass Certaldo, whose upper part has remained as it was in the Middle Ages. Further on you come across San Gimignano, which rises on a hill dominating the Val d’Elsa with its towers.
    7. Colle Val d’Elsa – Siena (40 km)
    From Colle Val d’Elsa you will cycle to the beautiful town of Siena, which is not only one of the most fascinating towns in Tuscany but is also in a particularly beautiful position, with lovely surroundings.
    8. Siena
    Departure after breakfast.


    Due to organisational reasons, weather conditions or provisions issued by local authorities, the itinerary may be subject to some changes before and/or during your holiday. For example, along the way you may find temporary deviations caused by roadworks, which cannot be foreseen; in this case please follow the indications you will find on site.



    2019, The Year of Leonardo



    A pilgrimage to Vinci is a must for any Leonardo enthusiast: just outside the village lies the humble house where he was born – now a museum – while the Museo Leonardiano is in the centre, featuring many of his inventions.

    In Florence, besides the absorbing Museo Galilei and countless events, we can also enjoy a unique exhibition at the Uffizi Gallery: “Water as Microscope of Nature: Leonardo da Vinci’s Codex Leicester” (on loan from Bill Gates, no less!).


    Uffizi Gallery site 
    Museo Leonardiano site




  • Route profile
    • Total length: 250 km
    • Total vertical up: 4,250 m
    • Terrain: 95% tarmac, 5% unpaved
    • Train connection among the overnight stays: NO
    • Possibility to shorten the itinerary by taking the train: NO

    Heavy, with sloping landscapes dotted with steeper inclines, but not overwhelmingly so. The daily distance is about 40 kilometres. Though the daily routes are not too long, they can be strenuous, so we do recommend being in reasonably good physical condition for this tour.

    Moderate: hilly areas, numerous climbs and downhill stretches. Suitable for regular cyclists with a good level of fitness.


  • How to get there

    Siena is connected with the following airports:
    Florence: 85 Km, Pisa: 150 Km.

    For further information on timetables and prices you can consult the following website:


  • Accommodation and meals

    We personally choose all the hotels mindful of your comfort as well as the proximity to cycling paths and any relevant local sites. 

    You will be accommodated in 3* hotels (sometimes a cosy B&B in Colle Val d’Elsa)

    All rooms have en suite facilities; some hotels may be without air conditioning.

    When you book the tour please specify the type of room requested:

    • double room is a room with one double bed
    • twin room is a room with two single beds
    • triple room is usually a room with one double bed and a single bed or a rollaway.
  • Bikes and accessories

    Girolibero’s City bikes are available in various sizes in unisex/women’s or men’s models. At the moment of booking, you can choose from the following bikes:

    • City bike 27-gear Shimano Deore
    • E-bike



    • aluminium frame 
    • mudguard 
    • rack 
    • comfort gel saddle
    • anti-puncture Schwalbe tyres
    • ergonomic bicycle grips
    • Speed Lifter system 



    • 1 cycle computer  
    • 1 Ortlieb one-sided saddlebag  
    • 1 front bar bag or 1 map holder 
    • 1 water bottle (0.75 l) 
    • 1 repair kit per room (which includes 1 spare inner tube, glue, patch, a pump, 2 allen keys and tyre levers) 
    • 1 combination bike lock


    At the moment of booking you can also rent helmets, suitable for head circumferences from 54 to 61. All helmets have a certification mark according to the DIN EN 1078 (CE) European norm.


  • Accompanying material

    The Information Pack (one per room) includes:

    • final hotel list: due to overbooking or organizational needs your hotel list may be changed just before your arrival
    • luggage labels to be fixed at each piece of baggage, which has to be carried
    • hotel vouchers to be given to the reception of each hotel on your arrival
    • Girolibero Greens booklets:
      1) Travel guide with valuable information about the history, artistic heritage, landscapes and natural treasures of the areas visited on the tour. Plus: local events, some great anecdotes, suggestions on how to make the best of an extended break along the route, and tips on local wining and dining.
      2) Detailed Maps of the itinerary: in colour and scaled 1:75.000/50.000, an altitude profile chart and maps of any historic city centres you would visit.
      3) Roadbook describing the cycling route, stage by stage. Great on its own or in conjunction with the maps.


  • By your side

    For the whole duration of your bike tour, you can contact us:

    • office +39 0444 1278430 from Monday to Friday 8:30-13:00 and 15:00-18:30
    • emergency phone number every day 8:00-20:00. The number will be specified in the Final Tour Details.
  • 3 Client reviews
    • Giuseppe

      Departure 03-10 September 2016

      Online from 15 September 2016

      Vacanza bella! Un susseguirsi di salite (alcune ripide) ed altrettante discese (allenante). Consigliata un po' di preparazione fisica o in assenza di questa bici elettrica .
      È superfluo aggiungere che gli scenari del Chianti sono fantastici per non parlare di Siena e Firenze.
    • Franco Eugenio

      Departure 2016

      Online from 12 September 2016

      Giro bellissimo ma molto impegnativo.
    • Edith und Willy, Österreich

      Departure 2016

      Online from 12 May 2016

      Liebe Anna,

      Wir hatten eine wunderschöne Reise. Alles hat perfekt funktioniert. Die Hotels waren super. Die Radrouten waren sehr schön.
      Wir freuen uns schon auf den Kathalog 2017, wo wir uns eine neue Reise aussuchen werden. Vielleicht nehmen wir auch Freunde mit,
      die wir mit unserer Begeisterung angesteckt haben.

      Vielen Dank für Deine nette Betreuung, das kompetente Service.
      Bis zum nächsten Giro, ciao, ciao!!!!!!

      Viele liebe Grüße aus Österreich
  • 1 Variations
  • 1 To combine with

Tour details


from 630 €

8 Days / 7 Nights, 3* hotels and B&B

Tour type




SA from 23.3 to 12.10.2019

Special departure dates for at least 5 people.



Season 1: 23.3 - 12.4 and 28.09 - 12.10.2019

Season 2: 13.4 - 17.5 and 8.9 - 27.9.2019

Season 3: 18.5 - 7.9.2019


Price per person

630 € in double room, 3* hotels (sometimes a cosy B&B in Colle Val D’Elsa)



  • 7 nights hotel accommodation
  • Breakfast buffet
  • Travel Guide, Maps, Roadbook
  • Luggage transportation
  • Hotline service


Not included 

  • Local taxes (approx 10-15 €)
  • Everything not mentioned in the section “included”



200 € single room

80 € season 2

110 € season 3

80 € Girolibero bike

190 € E-bike

15 € helmet


Extra nights in double/single room with breakfast:

60/90 € in Siena


100 € 3rd person in room

At Girolibero we believe in rewarding our customers: choose the most beautiful pictures or a video of your holiday, you can win a travel voucher worth € 300!
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