(3 reviews)

Self-guided Cycling / 2022 / 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’ll 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’ll 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’ll discover also picturesque villages where you’ll be tempted by the excellent Tuscan cuisine.
  • Day by Day


    1. Siena

    Individual arrival in Siena, superb medieval town. Easily distinguish it by old brick buildings and the crown of the city tower Torre del Mangia.


    2. Siena – Radda in Chianti (40 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 (30 km)

    Today you will discover Tuscany’s “road of wines”, where the famous Chianti Classico wine is produced. The route brings you to Greve pedalling through a lush green district with a countryside charm.


    4. Greve – Florence (45 km)

    You will cycle to Florence, Tuscany's capital known for its wealth in culture, architecture and art. This bustling metropolis is considered the birthplace of the Renaissance and upon your arrival you can immediately see hints of artisan decor embellished upon buildings and squares.  


    5. Florence

    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.



  • Route profile
    • Total length: 115 km
    • Total vertical up: 1950 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.


    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: www.trenitalia.com.


  • 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 3/4* hotels

    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 sofa bed.


  • Bikes and accessories

    Girolibero bikes are available in different sizes and frames:

    • Touring bike 27-gear Shimano Deore
    • E-bike 9-gear Shimano


    • aluminium frame
    • mudguard
    • rear rack
    • comfort gel saddle www.selleroyal.com
    • anti-puncture Schwalbe tyres
    • ergonomic bicycle grips
    • Speed Lifter system

    All rented adult bikes are equipped with:

    • 1 cycle computer  
    • 1 Ortlieb one-sided saddlebag
    • 1 front bar bag 
    • 1 water bottle (0.75 l)
    • 1 repair kit per room: 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 cm. All helmets have a certification mark according to the DIN EN 1078 (CE) European norm.



  • Accompanying material

    Before your arrival, you will receive an email from us with the digital information material. It contains:


    1. Link to download the App including maps, points of interest and GPS tracks (you can use the App offline, too)


    2. Link to download the tour information material in Pdf:

    • Tour notes
    • Final tour details
    • Travel guide with valuable information about the history, artistic heritage, landscapes and places of interest of the areas you pass through during your tour. Plus: local events, fun facts, suggestions on how to make the best of an extended break along the route, and tips on local wining and dining.


    3. Digital travel documents:

    • Final hotel list: due to overbooking or organizational needs your hotel list may be changed just before your arrival
    • Hotel vouchers to show to the hotel reception upon arrival
    • Luggage labels



  • By your side

    Staff support

    In the Final Tour Details you will find the contact phone numbers you can call during the tour in case of emergency.
    The Girolibero team is always available for you at the office number during office hours.

  • 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.
      Le seguenti impressioni sono state pubblicate prima del nuovo sistema di rating

      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

Tour details


from 460 €

5 Days / 4 Nights, 3/4* hotels

Tour type




Season 1: 30.03 - 12.04 and 28.09 - 12.10.2021

Season 2: 13.04 - 17.05 and 8.09 - 27.09.2021

Season 3: 18.05 - 7.09.2021

Price per person
460 € in double room, 3/4* hotels


  • 4 nights hotel accommodation with breakfast
  • App including maps, points of interest and GPS tracks
  • Digital tour information
  • Luggage transportation
  • Hotline service

Not included

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

Supplements per person
140 € single room
60 € season 2
90 € season 3

Extra nights in double/single room with breakfast:
65/95 € in Siena

Florence on request

Girolibero rental bikes including insurance against theft and damage:
60 € Touring bike
125 € E-bike

Additional bike accessories on demand:
15 € helmet (head circumference from 54 to 61 cm)

70 € 3rd person in room

2021 on hold
Sometimes taking risks is part of our job; however, this year we simply cannot take this risk. Here you can read why - and in the meantime we are preparing 2022, ready to roll again!
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