Cycling
Grand Tour of Tuscany
- IT026 / Italy
- Cycling Cycling tours Cycling holiday with accommodation in selected facilities, luggage transport, assistance. Details
- Self-guided Self-guided Travel at your own pace following maps, roadbooks and information material. When travelling, you can always count on our assistance.
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Comfort and accommodation
Four levels of comfort to describe the different types of accommodation.
Find out more about comfort on this trip under comfort and departures.
- Mar, Apr, May, Jun, Jul, Aug, Sep, Oct
- 5 days
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- linear from Pisa to Siena
- Discount for 3rd person in room
Highlights
If you have less than a week available, the route between Pisa and Siena is ideal to have a little taste of the enchanting region of Tuscany. As you cycle through vineyards and olives, you get the chance to explore medieval villages such as Casciana Terme, San Gimignano, and Monteriggioni. Don't forget to plan some culinary stops in the countless typical restaurants along the way!
- The historic villages that unfold one after the other
- The hills of the Val d'Elsa, among vineyards and olives
- The medieval centre of Siena and the scenographic Piazza dei Miracoli
What awaits you
This biking week is specifically designed for regular cyclists who are in good physical shape. The daily stages are not too long, about 45 km, but they cover hilly landscapes with numerous climbs and descents, including some steep inclines. This route is recommended only for those who are well-trained.
1. Arrival in Pisa
Welcome to the city that is famous throughout the world for its Leaning Tower: Pisa. Once you have settled in at your hotel, you can head to the scenic Piazza dei Miracoli to take a closer look at this bizarre bell tower, the city’s Cathedral next to it, the Baptistery, and the Campo Santo. This entire complex is listed as a UNESCO World Heritage Site and offers, in addition to its valuable monuments, the friendly and lively atmosphere of a university town.
2. On the pedals to Casciana Terme, among olive trees and vineyards
As you ride with the Arno river by your side, you reach Pontedera, a well-known industrial center located inland from Pisa. It is here where the Piaggio headquarters and the excellent Amedei chocolate factory are situated. The journey continues through the picturesque Tuscan countryside, passing by olive groves and vineyards, until you arrive at the final destination of the day: Casciana Terme, the “city of wellness.” Casciana is famous for its Etruscan roots and regenerating thermal water, which was discovered by Countess Matilda of Tuscany in the 12th century.
Shorten the stage You can take the train from Pisa to Pontedera station.
3. Towards San Gimignano/Colle Val d'Elsa, along the Via Francigena
Once again, you witness the beautiful vineyards as you make your way through the Val d’Elsa hills. Toward the end of the stage, keep an eye out for medieval towers. San Gimignano boasts 14 of them now, but in the past, the town’s noble families had built 72 of them to demonstrate their power. San Gimignano has been declared a UNESCO World Heritage Site and still retains its original medieval-style urban architecture, which is a true representation of the past. An alternative overnight stay is in Colle Val d’Elsa (70 km, elevation gain +1000m/-980m).
4. Along ancient paths to the heart of Tuscany, Siena
Say goodbye to San Gimignano and get in the saddle: the ancient paths of the Via Francigena lead you to the charming walled village of Monteriggioni, which is famous for its typical Italian architecture. The almost intact village walls stretch over a length of 570 meters and consist of 14 towers and two gates. Finally, you arrive in Siena, which is known for its historic streets and remarkable monuments. After exploring the city, you can recharge your batteries with a delicious dinner of authentic Italian dishes at one of the many eateries in the city center. Savor the rich flavors of tagliatelle with porcini mushrooms, classic pici, Cinta Senese, sweet cantucci, and ricciarelli, all of which are best enjoyed with a glass of Chianti. If your stage starts from Colle Val d’Elsa, the total length is 25 km (elevation gain +445m/-242m).
5. End of tour in Siena
Check-out after breakfast. If you still have time, we suggest spending the day exploring the city center, admiring the scenographic Piazza del Campo, or even hiking up the 400 stairs and enjoying the view from the top of the tower Torre del Mangia.
You will be accommodated in 3/4* hotels.
All rooms have en suite facilities and air conditioning.
2025
Departures on Saturday
go to online quote
Accommodation
- 4 nights accommodation
Meals
- 4 breakfasts
Hotels usually serve a continental breakfast. However, in some smaller hotels you may find the typical Italian breakfast, consisting of a hot drink, such as cappuccino or coffee, with fresh pastries, such as cake, croissants or toast and jam.
Luggage transfer
Your luggage will be transported from hotel to hotel starting from the first day of the standard tour until the last day of the tour.
For the luggage transportation we accept only 1 piece of luggage per person with max. 20 kg.
The service is not included in case of extra nights before or after the standard tour.
Before your departure, you will receive detailed guidance on allowable baggage, luggage labels, service hours.
Tour information
Before departure you will receive by email:
- the link to download the tour information material in Pdf (Tour notes and Final tour details)
- the hotel list
- the hotel vouchers to show to the hotel reception upon arrival
- the link to download the App including maps, roadbook, points of interest and GPS tracks (you can use the App offline, too)
When you arrive at the first hotel you will find the luggage labels.
Assistance
In the Final Tour Details you will find the contact phone numbers you can call during the tour in case of emergency.
Cancellation policy
In the event of unavoidable and extraordinary circumstances occurring at the place of destination or in its immediate surrounding area and having a substantial impact on the execution of the package or on the transport of travellers towards the destination, the traveller has the right to withdraw from the agreement before using the package, without paying withdrawal costs.
In all the other cases of withdrawal from the travel agreement, the traveller is always required to pay a withdrawal penalty. Read more
Withdrawal penalties
- 20% up to 30 days prior to departure date
- 25% from 29 to 21 days prior to departure date
- 50% from 20 to 14 days prior to departure date
- 80% from 13 to 6 days prior to departure date
- 100% from 5 days prior to departure date and no-show
Round trip
Travel to and from start and finish points not included
To pay on the spot
- Meals not mentioned in the section “What’s included”
- Tourist taxes (10-20€ per person)
They must be paid directly by you at check-in or check-out at the hotels. This fee varies depending on the hotel category, on the season and the number of days of stay. - Tips
Rental bikes and accessories
You can rent Girolibero bikes and accessories.
You can also cycle with your own bike, just make sure that all parts are functioning properly.
Additional excluded services
- Accommodation in single room
- Extra nights
It is possible to book extra nights in Pisa and Siena before or after the tour. Rental bikes are not included in case of extra nights. - Everything not mentioned in the section “What’s included”
You can rent the bike type that suits you best. You will find it at the starting point of the tour and you have to return it at the end of the last cycling stage: easy, isn’t it? Touring bikes, electric bikes, tandems, accessories: our mechanics know them down to the last bolt, assemble them and continually overhaul them at our headquarters or at the nearest base of operations. The rental of Girolibero bikes includes insurance against theft and irreparable damage. See Girolibero bikes in detail.
Unisex touring bike
- 28″ wheel
- 27 speed
- anti-puncture tires
- comfort gel saddle
- speedlifter twist T10 to easily adjust the handlebar height
- the only one suitable with children’s accessories
Unisex touring bike
- 28″ wheel
- 27 speed
- anti-puncture tires
- comfort gel saddle
- speedlifter twist T10 to easily adjust the handlebar height
- the only one suitable with children’s accessories
Specifically assembled by our mechanics, our touring bikes feature components and accessories that make it reliable and easy to ride, a perfect companion for your bike tour. Furthermore, thanks to the step-through frame, getting on and off your bike is easier.
Standard components
- bike bell
- side kickstand
- cycle computer
- front/rear lights
- front/rear mudguards
- bottle holder
- rear rack
Accessories included
- Ortlieb rear side pannier (12,5 l)
- repair kit (1 per room)
- handlebar bag (1 per room)
- lock
On guided tours, the handlebar bag and repair kit are only provided to those who ride individually.
Bosch unisex e-bike
- 28” wheel
- 9 speed
- anti-puncture tires
- comfort gel saddle
- speedlifter twist T10 to easily adjust the handlebar height
Bosch unisex e-bike
- 28” wheel
- 9 speed
- anti-puncture tires
- comfort gel saddle
- speedlifter twist T10 to easily adjust the handlebar height
Our e-bike is the right choice if you do not feel trained enough to spend more days on a saddle. You can easily adjust the assistance of the electric motor: from a mild pedaling support, to a more intense boost, which is especially useful on starts and uphill climbs. The battery charge covers an entire cycling stage, or even more if you don’t use it at full power all the time, and you can recharge it at the end of the day at the hotel .
Standard components
- bike bell
- side kickstand
- cycle computer
- frame lock
- front/rear lights
- front/rear mudguards
- bottle holder
- rear rack
Accessories included
- Ortlieb rear side pannier (12,5 l)
- handlebar bag (1 per room)
- battery charger
- battery key
- repair kit
- lock
On guided tours, the handlebar bag and repair kit are only provided to those who ride individually.
Men's touring bike
- 28″ wheel
- 27 speed
- anti-puncture tires
- comfort gel saddle
- speedlifter twist T10 to easily adjust the handlebar height
Men's touring bike
- 28″ wheel
- 27 speed
- anti-puncture tires
- comfort gel saddle
- speedlifter twist T10 to easily adjust the handlebar height
Specifically assembled by our mechanics, our touring bikes feature components and accessories that make it reliable and easy to ride, a perfect companion for your bike tour.
Standard components
- bike bell
- side kickstand
- cycle computer
- front/rear lights
- front/rear mudguards
- bottle holder
- rear rack
Accessories included
- Ortlieb rear side pannier (12,5 l)
- repair kit (1 per room)
- lock
- handlebar bag (1 per room)
On guided tours, the handlebar bag and repair kit are only provided to those who ride individually.
Ortlieb bag
- material: PD620/PS490 waterproof
- dimensions: 30×25×14 cm. (HxWxD)
- weight: 1300 g
- capacity: 12,5 l
Ortlieb bag
- material: PD620/PS490 waterproof
- dimensions: 30×25×14 cm. (HxWxD)
- weight: 1300 g
- capacity: 12,5 l
Waterproof side bag whose compact size makes it the ideal partner for short trips or shopping. Through the QL1 mounting system, it can be quickly and easily attached to the bike.
Repair Kit
Kit includes:
- 1 pump
- 1 inner tube
- 2 allen keys
- tyre levers
- patch
- glue
Repair Kit
Kit includes:
- 1 pump
- 1 inner tube
- 2 allen keys
- tyre levers
- patch
- glue
A repair kit (one for every two bikes) containing what is needed to change the inner tube in case of a puncture is provided for each reservation.
Mobile phone holder, which one to choose?
- Girolibero handlebar bag
- Generic phone holders
- SP Connect™ mount, the best on the market
Mobile phone holder, which one to choose?
- Girolibero handlebar bag
- Generic phone holders
- SP Connect™ mount, the best on the market
To attach your smartphone to the handlebar you have 3 options:
- use the Girolibero handlebar bag supplied free of charge (1 per room)
- buy a mobile phone holder in sports shops or major e-commerce outlets: for € 18-25 we recommend the models that clamp your mobile phone and its case like a vise.
- order the best product on the market, SP Connect™ with a special discount. The SP Connect™ mount is attached to the handlebar and works only with a special phone case. This case, which can also be used in everyday life, is slightly thicker than normal cases and is fixed to the handlebar mount with a simple click. The main advantage is that it is easy to attach and remove your phone, so you can immediately use it to take pictures or make calls, as well as grab it quickly when you want to stop cycling and have a break. Also, there are many other available accessories, including those for your car and writing desk. We recommend the Velcro Universal Mount SPC+ which costs € 29.90, which you can buy with a special 20% discount. The compatible phone case must be purchased separately and the price varies depending on your phone model. Visit the official SP Connect™ website and use the discount code TRAVEL20, which applies to all products.
Route profile
- Level: medium
- Total length: 145 km
- Terrain: 80% tarmac, 20% unpaved
- Train connection among the overnight stays: no
- Possibility to shorten the itinerary by taking the train: day 2
How to get there
Pisa is the starting point of the tour to be reached independently.
By plane
Pisa is connected with the following airports: Pisa: 5 km, Florence: 90 km.
From Pisa Galileo Galilei airport (PSA):
- shuttle PisaMover from the airport to Pisa train station (approx. 5 min)
- alternatively, you can arrange a private transfer to the hotel in Pisa to be booked independently. You can contact the following companies: Limousine Oritour or Autonoleggio Berrugi
From Firenze Amerigo Vespucci airport (FLR):
- tram from airport to Florence main train station Santa Maria Novella (approx. 20 min). From here train to Pisa (approx. 1/1h30)
- alternatively, you can arrange a private transfer to the hotel in Pisa to be booked independently. You can contact the following company: CO.A.VE.
For an overview of prices, airlines and flight schedules we suggest rome2rio.com or Google Maps, which also show options via train or bus, even for the last mile. For reliability and security, we recommend purchasing your flight on the official website of your chosen airline.
By train
For information on timetables and prices you can consult the Trenitalia official website.
By car
If you arrive by car, you can park the car in Pisa for the whole duration of the tour. Some hotels have a private parking place, while in other cases you have to use alternative car parks. No reservation is possible and you have to pay on site. You’ll receive all relevant information in the Final Tour Details.
Documents
If you are a citizen of the EU or of a Schengen country – i.e. most EU countries and four European Free Trade Association (EFTA) member states, Iceland, Liechtenstein, Norway and Switzerland – you are free to travel to other Schengen countries without having to go through border controls.
Even if you don’t need a passport for border checks within the Schengen area, it is still always highly recommended to take a passport or ID card with you.
If you are a non-EU national wishing to visit or travel within the EU, you will need a passport:
- valid for at least 3 months after the date you intend to leave the EU country you are visiting,
- which was issued within the previous 10 years
- and possibly a visa
You should apply for a visa from the consulate or embassy of the country you are visiting. If your visa is from a Schengen area country, it automatically allows you to travel to the other Schengen countries as well.
Do not forget your travel, health and/or car insurance documents.
For further information visit Your Europe official website.
Do not forget your travel, health and/or car insurance documents.
Always thoroughly check the document you travel with: expiration date and integrity.
Registration of documents is compulsory at check-in in hotels.
Language and time zone
The official language is Italian.
Italy is in the Central European Time (CET) Zone, 1 hour ahead of Greenwich Mean Time zone (GMT), and observes Daylight Saving Time.
Internet, telephone, electricity
Internet and telephone
With a European SIM card, roaming services are free throughout Europe. Please check your rates with your mobile/internet provider before departure.
The international phone prefix for Italy is +39.
Emergency telephone numbers
112 – Common Emergency Number. This is the European emergency number which can be called in any emergency from any telephone (landline and mobile phone). Calls are free.
113 – Police Help Number
115 – Fire Department
118 – Medical Emergencies
Electricity
The Italian electrical net is 220V – 50Hz.
Sockets are Schuko bipolar and comply with European regulations. In most hotels you will find adaptors for different types of plugs.
Currency
The currency in Italy is the euro (€).
Equipment and clothing
Cycling essentials
- handlebar mobile phone holder (we recommend the SP Connect™ system: if you buy it online you get a 20% discount using the code TRAVEL20)
- a power bank
- comfortable shoes with stiff soles
- padded cycling shorts
Personal equipment
- basic first aid kit which includes sticky bandages, gauze, and low-grade disinfectant
- sunglasses for eye protection
- protective sun lotion
- insect repellent
Clothes
- light weight waterproof/windproof tops
- leggings and long-sleeved tops for cooler mornings or evenings
- small close-fitting rucksack to carry small items during the day while cycling
- swimsuit
- clothes to cover your shoulders when you visit churches
Read carefully
Tour programme variations
- 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.
Special diets
- If you are vegetarian, gluten-intolerant, allergic to some specific ingredients/substances or if you suffer from any other kind of allergies please indicate it at the moment of booking. We will pass the information on to the hotels, but we cannot guarantee that all dietary requests will be met. Sometimes it is difficult to find particular food, for example gluten-free food, so we suggest that you bring your own snacks just in case.
Travel insurance
- It is advisable to take out an insurance policy against expenses arising from cancellation of the tour package, accidents, luggage (loss and damage), as well as a contract covering expenses in case of repatriation. Insurance policies are not included in the tour package offered by the operator.
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