Self-guided Cycling


Italy / Tuscany variation 1

Siena, Chianti District and 2 nights in 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.

    2. Siena – Radda in Chianti (45 km)
    From Siena you 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 in Chianti (40 km)
    The route brings you to Greve over the rounded hills with beautiful views.

    4. Greve in Chianti – Florence (40 km)
    You will cycle to Florence, capital of Tuscany, and admire the masterpieces of Leonardo and Michelangelo.
    5. Florence
    A full day to spend visiting Florence. The city is often considered the birthplace of the Italian Renaissance and was long ruled by the Medici family.
    6. Florence – Colle Val d’Elsa (40 km by train + 25 km by bike)
    In the morning a short train transfer will bring you to Certaldo. From here you will then cycle further up to Colle Val d’Elsa.
    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 the holiday.
    Along the way you may find temporary deviations (for example road works) which cannot be foreseen; in this case each rider can decide autonomously how to deal with these stretches.


  • Route profile
    • Total length: 190 km
    • Total vertical up: 3,380 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. The hotels of this tour are:
    Category A: 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
    • Electro-bike



    • aluminium frame 
    • mudguard 
    • rack 
    • comfort gel saddle
    • anti-puncture Schwalbe tyres
    • ergonomic bicycle grips
    • Speed Lifter system (only for City bikes)



    • 1 cycle computer  
    • 1 Ortlieb one-sided saddlebag  
    • 1 front bar bag or 1 map holder 
    • a 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
    • restaurant vouchers (if you have booked half-board)
    • 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
    • Donna

      Departure 2010

      Online from 20 August 2010

      We have just returned from an amazing trip through Tuscany! The routes were well thought out, the maps and directions very clear and easy to follow, and the hotels were nice and in great locations. Thank you to Girolibero---this was the very best way to experience Tuscany. We look forward to our next trip!
    • O. B. S. - USA

      Departure 2009

      Online from 03 March 2010

      Antonio, I have been meaning to write you and thank you for your efforts in making our bicycling trip to Tuscany a fabulous one. Your iteniary was excellent!
    • Teresa G - USA

      Departure 2009

      Online from 03 March 2010

      We are about 3-months overdue with our trip report, but we do want to let you know what a wonderful trip we had cycling through Tuscany. Everything was well-planned from the choice of hotels to bicycle rentals to road trip directions and route choices. The description of the degree of route difficulty, in our case "leisurely", was spot on: a reasonable degree of fitness was required as this route consisted of many rolling hills. Our group paid attention to this advice and we are glad to say we felt our level of fitness matched the terrain. It was quite clear that the road book of directions had been written by people who had ridden along each route, as the directions were very precise in their description of where to turn and included a double check feature of stating what the distance traveled should be at the time of turning. As our group members were committed to enjoying all the tastes of Tuscany as much as the sights and sounds, we assessed each stage of our trip as being a one-scoop or a two-scoop gelato day depending on how challenging the hills were. 
We do have two comments to make about hotel choices. While the hotel in Tavarnelle (Park Hotel Chianti) was fine, its location meant that we ended the day going downhill, knowing that the next morning we started the day immediately with a steep climb back up the same hill and a ride of 3km before starting the next stage. The other hotel comment concerns the first stage ending in Radda. Hotel Podere Le Vigne had been reserved for us, but, unfortunately, closed down due to a lack of business. This information was communicated to us by the owner of a substitute hotel driving his car up the last hill of the day and stopping to talk to us as we were resting before completing our climb, although two of our members had in fact reached the top. The result was that we had to ride back down the mountain, knowing that we had to reclimb it in the morning. The hotel was brand new and very beautiful, and the owners drove us back up the mountain to Radda for dinner later, all of which compensated us well for the sudden change, but other groups doing the same tour spent several hours at the hotel in Radda, which had not been locked up, waiting to be shown to their rooms. As they had made it to the hotel, they were, fortunately, able to leave their bicycles locked up there and were taken down to the alternative hotel by car, so that they did not have to repeat the climb the next day. They too felt that the alternative arrangements were fine. On returning to Siena at the end of our trip we felt victorious and felt we had experienced Tuscany in the best way possible. Girolibero provided a first-class service (including excellent bicycles) and we look forward to doing another trip. Teresa G.
  • 2 Variations
  • 2 To combine with

Tour details


from 650 €

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

Tour type




SA from 7.04 to 6.10.2018
Special departure dates for at least 5 people.



Season 1: 7.04 - 4.05 and 23.09 - 6.10.2018
Season 2: 5.05 - 22.09.2018


Price per person

650 € in double room, 3* hotels and b&b



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


Not included

  • Local taxes (approx 10-15 €)
  • Train transfer: Florence–Certaldo (approx. 50 min., 10 € per person, bike incl.)
  • Everything not mentioned in the section “Included”



220 € single room
80 € season 2
170 € half board: 6 dinners (3-course meals, beverages not included)
80 € Girolibero bike
190 € Electro-bike
15 € helmet
Extra nights in double/single room with breakfast:
60/90 € in Siena
from 75/130 € in Florence



100 € 3rd person in room

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