Italy
Cycle tour Tuscany: Pisa, Chianti, Siena and Florence
7 days
Bike tours
Departure days: Saturday
240km
Intermediate
About this 7-day cycle tour in Tuscany
Cycle through the heart of Tuscany on this 7-day tour: from Pisa’s Leaning Tower, through the rolling vineyards of the Chianti wine region, to medieval Siena and on to Florence, the birthplace of the Renaissance. This route winds past olive groves, medieval hilltop villages and historic wine estates — with a glass of Chianti waiting at the end of every day.
Please note: this is a demanding route for experienced, well-trained cyclists. Daily stages aren’t especially long (around 45 km), but wind through hilly terrain with regular steep climbs.
Also, check out our other bike tour in Tuscany.
Cycle through Tuscany’s vineyards, medieval towns and rolling hills from Pisa to Florence.
Highlights of this bike tour in Tuscany
- San Gimignano – medieval town with impressive towers and UNESCO World Heritage status
- Siena – atmospheric city with the famous Piazza del Campo and a remarkable cathedral
- Monteriggioni – charming fortified village surrounded by ancient walls
- Chianti – rolling hills, vineyards, and authentic Tuscan villages
- Casciana Terme – relax in natural thermal baths
- Florence – Renaissance city full of art, culture, and Italian elegance
Day-by-Day Itinerary
Your Tuscan cycling holiday begins in Pisa, home to the world-famous Leaning Tower of Pisa on Piazza dei Miracoli, a UNESCO World Heritage Site. This iconic square also features the impressive cathedral and baptistery, making it the perfect place to start your journey.
Beyond its famous landmarks, Pisa is a lively university city with charming squares, cafés, and traditional trattorias where you can experience authentic Italian atmosphere. End your first day with a relaxing walk along the Arno and enjoy the perfect beginning of your cycling holiday in Tuscany.
Today you cycle through the heart of the Tuscan countryside, passing vineyards, olive groves, and winding cypress-lined roads. Along the way, you pass Pontedera, known for the historic Piaggio Vespa factory and local wine estates.
Your day ends in Casciana Terme, a charming thermal spa town where natural hot springs have been enjoyed since Roman times. Relax in the thermal baths or enjoy a glass of local wine — the perfect ending to your first cycling day in Tuscany.
Today you follow the historic Via Francigena, the ancient pilgrimage route through Tuscany, surrounded by rolling hills, vineyards, and olive groves.
In the afternoon you arrive in San Gimignano, the famous UNESCO World Heritage town known for its medieval towers. Stroll across Piazza della Cisterna, taste a glass of Vernaccia wine, and enjoy panoramic views over the Tuscan countryside.
If you stay in Colle di Val d’Elsa, you will discover a charming town famous for its glassmaking tradition and picturesque streets filled with artisan shops.
Today you continue cycling through the heart of Tuscany towards beautiful Siena. Along the way, you pass Monteriggioni, a perfectly preserved medieval fortified village once described by Dante Alighieri.
Your destination is Siena, one of Italy’s most remarkable historic cities. Piazza del Campo, home to the famous Palio di Siena, forms the lively heart of the city. Visit the impressive gothic cathedral and enjoy an espresso on a sunny terrace.
Today is all about Tuscan wine, castles, and panoramic landscapes. You cycle through the world-famous Chianti region, known for vineyards, medieval villages, and elegant country estates.
Along the route, stop at Castello di Brolio, where the famous Chianti Classico wine is produced. Continue through Radda in Chianti and Panzano in Chianti, two charming villages with lively squares and inviting wine shops.
You finish in Greve in Chianti, considered the heart of the Chianti region. At Piazza Matteotti you can taste local wines or simply enjoy the view over the rolling hills.
Your final cycling day takes you through picturesque villages and vineyards towards Florence. Along the way, you pass Mercatale in Val di Pesa and Impruneta, both known for terracotta craftsmanship and local wine cellars.
As you approach the city, the impressive Florence Cathedral appears on the horizon — a fitting finale to your journey. Walk across Ponte Vecchio, admire the Duomo, and enjoy a well-deserved gelato on a sunny terrace.
After breakfast, your cycling holiday comes to an end. Feel free to stay an extra day in Florence to enjoy its art, culture, and gastronomy. Visit the Uffizi Gallery, admire David by Michelangelo, or stroll through the lively San Lorenzo Market.
A relaxed ending to an unforgettable journey through the heart of Tuscany.
Sights along the route
Leaning Tower of Pisa
The Leaning Tower of Pisa is the iconic symbol of Tuscany and one of Italy’s most famous landmarks. Together with the cathedral and baptistery, it forms the impressive Piazza dei Miracoli, a UNESCO World Heritage Site.
From the top, you can enjoy beautiful views over Pisa and the surrounding Tuscan hills, a perfect start to your cycling holiday in Tuscany.
Tuscan hills
The Tuscan Hills create a picturesque landscape of vineyards, olive groves and cypress-lined roads. As you cycle, the scenery gently rises and falls, with rustic villages and panoramic views appearing along the route. A day of cycling through this heart of Tuscany offers pure enjoyment of nature, tranquillity and authentic Italian charm.
San Gimignano
San Gimignano, a UNESCO World Heritage town, is known for its medieval towers and atmospheric squares such as Piazza della Cisterna. Walk through narrow streets, taste the local Vernaccia wine, and enjoy impressive views over the Tuscan hills. A historic highlight of your cycling holiday through Tuscany.
Siena
Siena is one of Italy’s most beautiful cities and an absolute highlight of your cycling holiday in Tuscany. The heart of the city is Piazza del Campo, where the famous Palio di Siena takes place twice a year. Wander through narrow streets, admire the gothic Siena Cathedral, and enjoy an espresso or gelato while overlooking the terracotta rooftops of this atmospheric city.
Chianti regio
The Chianti region is one of the most picturesque areas of Tuscany. The route takes you past vineyards, castles, and charming villages such as Radda in Chianti, Panzano in Chianti, and Greve in Chianti. Visit Castello di Brolio and taste the world-famous Chianti Classico wine. The rolling hills and cypress-lined roads make this stage a visual and culinary highlight.
Florence
Florence is the artistic capital of Tuscany and the perfect finale to your journey. In this Renaissance city, you can cycle or walk past world-famous highlights such as Florence Cathedral, Ponte Vecchio, and the Uffizi Gallery, where works by Michelangelo and Sandro Botticelli can be admired. Florence is an open-air museum filled with culture, beauty, and history.
Prices and departure dates
The prices below are per person based on two people sharing a room, including breakfast, luggage transfer, and VAT.
2026
| Period | Double / twin room | Single room |
|---|---|---|
| 5 sep – 25 sep | € 1.160 | € 1.510 |
| 26 sep – 10 okt | € 990 | € 1.340 |
2027
| Period | Single room | Double room |
|---|---|---|
| 17/04/2027 – 07/05/2027 | € 1.684 p.p. | € 1.277 p.p. |
| 08/05/2027 – 03/09/2027 | € 1.739 p.p. | € 1.332 p.p. |
| 04/09/2027 – 24/09/2027 | € 1.684 p.p. | € 1.277 p.p. |
Departure dates: every Saturday between March and October.
Alternative departure dates are possible for groups of at least six people.
Included
- 6 overnight stays in comfortable 3- and 4-star hotels
- Daily breakfast
- Luggage transfer from hotel to hotel (1 suitcase per person, max. 20 kg)
- Digital route app with GPS tracks, maps, roadbook, and points of interest
- Travel documents including hotel list, hotel vouchers, and travel guide (PDF by email)
- Telephone assistance during the trip
Not included
- Travel to and from the start and end point (Pisa – Florence)
- Lunches, dinners, and drinks
- Tourist tax (payable locally)
- Rental bike or e-bike (optional)
- Travel insurance, personal expenses, and tips
Optional extras
Prices per person, including VAT.
| Service / Extra | Price p.p. |
|---|---|
| Comfort Touring Bike (27 gears) | €132 |
| E-bike | €320 |
| Helmet Rental | €20 |
| Extra nights | On request |
| Private Transfer | On request |
Practical information
- Travel type: self-guided cycling holiday
- Duration: 7 days / 6 nights
- Distance: 40–55 km per day
- Level: moderate (hilly terrain)
- Start point: Pisa
- End point: Florence
- Accommodation: small-scale hotels and agriturismos, including breakfast
- Luggage: daily luggage transfer included
- Navigation: route app and GPS tracks
- Departure: daily from April to October
Getting to Pisa
Pisa is the starting point of the tour. You will make your own way to Pisa and are responsible for arranging your own transport to the starting point and your hotel.
By plane
Pisa can be reached via two airports. Pisa Galileo Galilei Airport is approximately 5 km from the city, while Florence Amerigo Vespucci Airport is around 90 km away.
From Pisa Galileo Galilei Airport (PSA)
From the airport, you can take the PisaMover, which connects the airport directly with Pisa railway station. The journey takes approximately 5 minutes.
Alternatively, you can arrange a private transfer to your hotel in Pisa. For this, you can contact Limousine Oritour or Autonoleggio Berrugi.
From Florence Amerigo Vespucci Airport (FLR)
From Florence Airport, take the tram to Florence’s main railway station, Santa Maria Novella. The tram journey takes around 20 minutes. From the station, you can continue by train to Pisa, with the journey taking approximately 1 to 1.5 hours depending on the connection.
You can also arrange a private transfer directly to your hotel in Pisa. For this option, you can contact CO.A.VE.
For information about flight options, prices and schedules, you can use online travel planners. These also provide information about travelling by train or bus. For the most reliable and secure booking experience, we recommend booking your flight directly through the airline’s official website.
By train
Travelling by train is a comfortable and environmentally friendly way to reach Pisa. The city’s main railway station is Pisa Centrale.
You can use Trainline to compare train times, prices and different international rail connections.
By car
If you are travelling by car, you can leave your vehicle parked in Pisa for the duration of the tour. Some hotels offer private parking. If your hotel does not have parking facilities, alternative parking areas are available nearby.
Parking spaces cannot be reserved in advance and payment is made locally. Detailed information about parking options will be provided in the final tour information.
Frequent asked questions about this Tuscany bike tour
No, this route requires good fitness; daily stages include steep climbs through the Chianti hills.
Self-guided, using GPS app and roadbook, with phone support available.
Yes, this is a one-way (linear) route ending in Florence; return travel is not included.
This route is more demanding (more elevation gain, aimed at experienced cyclists) and focuses on the Chianti wine region and Siena, while the Pisa to Florence tour is more accessible and travels via Lucca and Montecatini.
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