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Self-guided Cycling / 2022 / Original tour

Web code IT036

Italy / Tuscany

Grand Tour: Pisa, Siena and Florence

The landscape of Tuscany is one of the most beautiful and evocative, with rolling hills laced with verdant vineyards and cypress trees lining the roads. You will travel on a variety of routes, experiencing all the wonders Tuscany has to offer: from fine panoramas to culture and of course, a delicious cuisine! This unique route involves a jumpstart in Pisa and its leaning tower, a passing through Siena, superb medieval town, a trailing by the road of wines and the spectacle of Florence, the cradle of Renaissance. In between the paths, you will enter picturesque villages and rich hillsides filled with wineries.
  • Day by Day


    1. Pisa

    Individual arrival. The city is famous all over the world for its magic Piazza dei Miracoli with the characteristic leaning tower, the bell tower of the city cathedral. Part of the UNESCO World Heritage list since 1987, besides a large number of monuments it also offers the friendly and lively atmosphere of a university city.


    2. Pisa - Casciana Terme (45 km)

    Along the river Arno you will reach Pontedera, a rather modernized district, home to the wine company Castellani, and a sweets factory called Amedei. Your ride will take you through olive groves and vineyards, perfect for an immersion in nature. Finally you will reach the thermal town Casciana Terme, famous for its Etruscan roots, where thermal water was discovered by 12th century Countess Matilda of Tuscany.


    3. Casciana Terme - San Gimignano/Colle Val d’Elsa (50/70 km)

    Following the Via Francigena through vineyards and rolling hills you will arrive at San Gimignano, a hilltop village offering medieval landscapes. This UNESCO-awarded walled hamlet is known for its many towers. And in the evening, treat yourself with in the local exquisite cuisine!


    4. San Gimignano/Colle Val d’Elsa - Siena (45/25 km)

    By taking the olden paths of the Via Francigena, you'll be welcomed by the views of Mount Maggio and the castle of Monteriggioni, Dante's subject in his famous literary pieces. Siena, superb medieval town, is just ahead; easily distinguish it by old brick buildings and the crown of Torre del Mangia. 


    5. Siena - Radda in Chianti (40 km)

    Today first stop is Castagnolli, where you will admire the Brolio Castle, home to the Ricasoli family and today a well-managed wine cellar, too. Then you will reach Meleto Castle, its stern-looking architecture tucked in the elevated, tree-covered lands. End of the daily stage is Radda in Chianti, a classic Chianti village nestled inside the verdant hill region, among remnants of the Etruscan age.


    6. Radda in Chianti - Greve in Chianti (30 km)

    Today you will discover Tuscany’s “road of wines”! Pedalling off from Radda you'll reach Panzano, a lush green district with a countryside charm and get a glimpse of Montefioralle, a medieval town. Greve in Chianti is up next where the famous Chianti Classico Wine Festival is held every year in September. A sip of the local wine will fire up your senses.


    7. Greve in Chianti - Florence (45 km)

    Your last cycle day will bring you to a small town called Mercatale, where you will be given wine-tasting opportunities from its local wine cellars.  After ten kilometres trot off to Impruneta, a neighbouring district filled with terracotta art. Back on your saddle, Florence is waiting for you! Tuscany's capital is known for its wealth in culture, architecture and art. This bustling metropolis is considered the birthplace of the Renaissance and you can immediately see hints of artisan decor embellished upon buildings and squares.


    8. 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: 255 km

    Total vertical up: 3.495/3540 m

    Terrain: 70% tarmac, 30% unpaved

    Train connection among the overnight stays: NO

    Possibility to shorten the itinerary by taking the train: day 2


    Heavy, with sloping landscapes dotted with steeper inclines, but not overwhelmingly so. The daily distance is about 45 kilometers. 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

    Pisa is connected with the following airports:

    Pisa: about 5 km, Florence: about 90 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. 


    According to your category of choice you will be accommodated in:

    • Cat. A: 3/4* hotels
    • Cat. B: 3* hotels


    All rooms have en suite facilities and 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
    • 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


    Please check all documents thoroughly and let us know if anything is missing. 



  • 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.


Tour details


from 730 €

8 Days / 7 Nights, 3* hotels

Tour type




Season 1: 27.03 - 23.04 and 25.09 - 9.10.2021

Season 2: 24.04 - 14.05 and 5.09 - 24.09.2021

Season 3: 15.05 - 4.09.2021


Price per person

730 € in double room, Cat. B: 3* hotels

830 € in double room, Cat. A: 3/4* hotels 



  • 7 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 15-20 €)
  • Everything not mentioned in the section “Included” 

Supplements per person

190/240 € single room (Cat. B/A)

80 € season 2

120 € season 3

Extra nights in in double/single room with breakfast:

60/90 € in Pisa Cat. B

100/160 € in Pisa Cat. A


Girolibero rental bikes including insurance against theft and damage:
85 € Touring bike

195 € E-bike

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



120/150 € 3rd person in room (Cat. B/A)

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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