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Self-guided tours


Italy / Tuscany

The heroes' hills

Savour your visit to the birthplace of the Italian Renaissance with our self-guided "Giro of Tuscany" tour that includes some action-packed biking on some of the country's most beloved landscapes. Ride along mountain ranges and fertile plains as you pedal from city to city; starting off with the architectural wonders of Pisa to the artistically inspired city of Florence. You will pass by the famous road of wines, where a sip of the local Chianti or Brunello di Montalcino will help motivate you to continue on your journey. The local cuisine will surely quell your hunger, and the numerous pastoral views, full of well-preserved castles and cathedrals, will feed your visual senses. In addition, the eager smiles of the locals will welcome you into their region.
  • 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-Volterra (75 km, vertical up 810 m)
    Your first day of cycling is a less strenuous ride starting from the city of Pisa. Cycling along the Arno River you will reach Pontedera, home to the wine company Castellani, and a sweets factory called Amedei and then Ghizzano, a pleasant village surrounded by vineyards. Finally you arrive to Volterra, a walled medieval mountaintop town famous for its alabaster works. Immerse yourself in the backdrop and enjoy its local sights, such as the Roman Theatre and the Etruscan museum Guarnacci.

    3. Volterra-Siena (70 km, verticale up 1140 m)
    Traveling along the Via Francigena you will arrive to San Gimignano, where you will experience a legitimate taste of a medieval city. This UNESCO-awarded walled hamlet is known for its many towers. Visit Colle Val d'Elsa, dubbed as Italy's Bohemia. This area, named after an old Etruscan hero, is known for being a significant industrial center with medieval architecture. You'll even get to visit small, busy villages before you reach Monteriggioni and its remarkable Roman abbey (Abbadia a Isola) before your arrival in Siena, easily distinguish by old brick buildings and the crown of Torre del Mangia.

    4. Siena-Montalcino-Pienza-Siena (120 km, verticale up 1350 m)
    A route that follows the Cassia road south to the wonderful town of Montalcino. After about 40 km, the ascent that takes you up to the town is intimidating, but it opens up into the most fabulous panorama and once at the top your reward is a glass of good wine, bread and salami. The rest will get you ready to tackle the next uphill-downhill stretch that takes you to Pienza and then back to Siena. Variation 85 km, verticale up 655 m.

    5. Siena-Radda in Chianti (45 km, vertical up 970 m)
    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. Cross the town of Gaiole in Chianti, the historic world center of Heroic cycling. 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-Florence (70 km, vertical up 970m)
    Today you will discover Tuscany’s “road of wines”! Indulge yourself in the local wine flavors and take a break stop at Greve's public square. You'll recognize it easily--it's a triangle! Your last cycle day will bring you even to a small town called Mercatale, a little town surrounded by the hills of Chianti, also famous for its wineries. 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.

    7. 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: 380 km
    Total vertical up: 5,240 m

    This is a demanding tour because of the sloping landscape of Tuscany. There are some long and difficult ascents. However, it is easy to shorten the stage or to find different easier ways to the next hotel. Some short stretches of dirt road to reach panoramic views or points of interest.

    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: 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 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

    The rental bike for this tour is a high-end roadbike with top range carbon frame.

    Due to the lack of rear rack these bikes do not have panniers. We suggest you to bring a small backpack.

    We remind you that you are responsible for the rental bike and its accessories during the whole tour. The bicycle must always be locked and possibly secured to a pole, even for short periods.

    A bicycle rental contract has to be signed on the spot.

    We remind you to bring you own pedals (and wrench to fix them).

    All rented adult bikes are equipped with:

    • 1 bottle cage
    • 1 repair kit (2 inner tubes, pump, tire levers)
    • 1 combination bike lock


  • 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 €

7 Days / 6 Nights, 3/4* 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, 3/4* hotels


  • 6 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"

210 € single room
80 € season 2
120 € season 3

Extra nights in double/single room with breakfast:
100/160 € in Pisa
Florence on request

Rental bikes:
250 € high-end road bike

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

150 € 3rd person in room

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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