The Rolling Hills of Tuscany by bike
- From 889 € / pers.
- 7 days / 6 nights
- From end of March to October
- Departures: Saturdays
- Level: moderate / rather sporty
- Average: 47 km/day
- Electric bike rental available
- Luggage transfer included
Highlights
- The cultural cities of Pisa, Florence, Siena, … cradles of the Renaissance
- The bucolic landscapes of the Tuscan countryside, scattered with cedars, cypresses, olive trees, and vineyards
- The gastronomy and wine of Tuscany, whose reputation precedes them
- The picturesque villages, with their red tiles and typical tower houses
- A great density of things to discover, where everyone will find their happiness
Highlights :
- The cultural cities of Pisa, Florence, Siena, San Gimignano… cradles of the Renaissance
- The bucolic landscapes of the Tuscan countryside, scattered with cedars, cypresses, olive trees, and vineyards
- The gastronomy and wine of Tuscany, whose reputation precedes them
- The picturesque villages, with their red tiles and typical tower houses
- A density of things to discover, where everyone will find their happiness
From 889 € / pers.
- 7 days / 6 nights
- From end of March to October
- Departures : Saturdays
- Level: moderate / rather sporty
- Average: 47 km/day
- Electric bikes available
- Luggage transfer included
TUSCANY BY BIKE
Tuscany, with its picturesque landscapes and exceptional cultural heritage, is a dream destination for cycling enthusiasts. This iconic Italian region, also known as the cradle of the Renaissance, will enchant you with its colours, winding paths, twisted olive trees, generous vines and fragrant cypress trees.
YOUR ITINERARY
The itinerary we propose here, "Rolling Tuscany", is a 7-day itinerary. During your tour, you will explore the surprising Tuscan countryside, home of rolling green hills, endless vineyards, charming medieval villages, and cities such as Florence, Pisa, Siena, and San Gimignano, whose very names already evoke a thousand-year-old culture and the Italian dolce vita.
Throughout the trip, you will stay in charming accommodation and have plenty of free time to stroll through the narrow streets of the many villages you pass through, sample local specialities, and visit places steeped in history. Discover the details of the itinerary in the "day-by-day" tab.
Buon viaggio !
💡 Alongside this "Rolling Tuscany" itinerary, we also offer the tour "Tuscany, the Cradle of the Renaissance". Although both tours are a delightful blend of culture and nature, the "Cradle of the Renaissance" itinerary is more focused on typical cultural towns and villages and remains mainly on the plains, whereas "Rolling Tuscany" is a little more sportive and takes you on an adventure through the region’s picturesque rolling countryside. Both itineraries pass through Pisa and Florence. The "Cradle of the Renaissance" route also passes through Lucca, whereas the "Rolling Tuscany" route includes the hilltop town of San Gimignano and Siena, with its famous Piazza del Campo.
DAY-BY-DAY PROGRAMME
Day 1: Arrival in Pisa
The city of Pisa is world-famous for its enchanting Piazza dei Miracoli and its iconic Leaning Tower. The bell tower of the city's cathedral is also unique. Listed as a UNESCO World Heritage site since 1987, the city offers not only a large number of monuments but also the friendly, lively atmosphere of a university town.
Day 2: Pisa – Casciana Terme
50 km | 
+290 m
Along the Arno river, you will reach Pontedera, a fairly modern town that is home to the Castellani wine company and a confectionary factory called Amedei. Your journey will take you through olive groves and vineyards, immersing you in the Tuscan countryside. You will finally reach the spa town of Casciana Terme, famous for its Etruscan roots and thermal waters.
Day 3: Casciana Terme - San Gimignano
50 km | +755 m
Following the Via Francigena, a pilgrimage route connecting Canterbury to Rome, through vineyards and rolling hills, you will arrive at San Gimignano, a hilltop village offering medieval landscapes. This UNESCO-listed fortified hamlet is known for its many towers. In the evening, treat yourself to delicious local cuisine in one of the many restaurants in the town!
Day 4: San Gimignano - Siena
45 km | +740 m
Still following the medieval pilgrimage routes of the Via Francigena, you will be amazed by the views of Mont Maggio and the castle of Monteriggioni, mentioned by Dante in his famous literary works. Siena, another superb medieval city, is just ahead; you can easily spot it with its old brick buildings and the crown of the famous Torre del Mangia.
Day 5: Siena – Greve in Chianti
55 km | +935 m
Today, the route takes you through the enchanting landscapes of Chianti. Leave the medieval splendour of Siena and ride through green hills dotted with lush vineyards and slender cypress trees. On the way, treat yourself to a stop in Greve in Chianti, a charming town in the heart of the Chianti wine region, where you can sample local wines and discover authentic Tuscan cuisine in one of its picturesque trattorias.
Day 6: Greve in Chianti – Florence
35 km | + 660 m
On this final stage, you will cycle through the rolling hills of the Chianti, enjoying panoramic views of vineyards and olive groves. As you approach Florence, admire the skyline dominated by the city's red domes. Once you have arrived in the capital of Tuscany, soak up its rich artistic and architectural heritage, and why not enjoy a well-deserved gelato on the banks of the Arno.
Day 7: Florence
End of the tour after breakfast. We recommend setting aside at least the day to visit Florence at your own pace. It will be up to you to decide how to spend your time in one of the most beautiful cities in the world! The capital of Tuscany is known for its wealth of culture, architecture, and art, and is considered the birthplace of the Renaissance.
For example, you could start your day by exploring the city's iconic sites, such as the majestic Cathedral of Santa Maria del Fiore, also known as the Duomo, with its famous dome designed by Brunelleschi (the largest masonry dome in the world at 45.5 metres in external diameter). Afterwards, you could get lost in the narrow streets of the historic centre, discovering artistic treasures at every corner, from Renaissance palaces to churches adorned with frescoes.
For a more immersive cultural experience, you could choose to visit Florence's world-famous museums, such as the "Galleria degli Uffizi" (Uffizi Gallery), home to masterpieces of the Italian Renaissance, or the "Galleria dell'Accademia" (Accademia Gallery) where you can notably admire Michelangelo's iconic sculpture, the David.
If you prefer to soak up the lively atmosphere of the city, you could opt for a stroll along the Arno, admiring Florence's famous bridges, such as the Ponte Vecchio, with its traditional artisan shops. Then, why not sit down at an outdoor café terrace on the Piazza della Signoria, watching the world go by while enjoying an authentic Italian coffee?
Finally, for a relaxing break, you have the option of escaping the bustle of the city by walking through the beautiful Boboli Gardens, which offer an oasis of greenery and tranquillity in the heart of Florence.
ACCOMMODATION
Regardless of the level of comfort chosen, we favour authentic, human-scale accommodation that inspires comfort, conviviality, and well-being. We also strive to ensure that they are well-located: easily accessible by bike, and close to amenities and points of interest.
AVAILABLE CATEGORIES
3 / 4 ★ Hotels
A selection of addresses combining modern comfort and authenticity.
Photo provided as an example to illustrate the type of accommodation for each category.
Always included:
- Breakfast
- En-suite bathroom
- Bike storage
- Restaurant(s) within walking distance
- Convenient location
CHOOSING YOUR BIKE
Whether you choose a rental bike or set off with your own, it is essential to have a bike that is suited to the requirements of the route as well as your own needs.
RENTAL BIKES
We offer high-quality trekking bikes and/or electric bikes, equipped with all the essential accessories. Equipment for children is also available.
Trekking/Touring bikes
Versatile bikes with 27 gears, making them ideal for tackling the occasional hill without too much effort.
Electric bikes (e-bikes)
Bikes equipped with a BOSCH motor, 9 gears, and puncture-resistant tyres.
Photos are for information purposes. Bikes subject to availability.
Accessories included:
- Waterproof rear pannier
- Lock
- Repair kit
- Helmet(s) on request (€15/person)
IF YOU ARE BRINGING YOUR OWN BIKE
Before departure, carefully check the condition of your bike: brakes, tyres, sprockets, derailleur, chain, etc.
You could potentially be far from anywhere in the event of a mechanical issue!
Which bikes are suitable?
- Trekking/Touring bikes
- Mountain bikes (MTBs)
- Gravel bikes
- E-bikes with good range.
- Road bikes
- City bikes
DIFFICULTY: SUSTAINED (hilly terrain)
➡️ The stages are moderately long (approximately 3 to 4 hours of cycling per day - max. 5).
This pace suits most people: it strikes a balance between the pleasure of cycling and discoveries along the way.
➡️ The elevation gain is quite pronounced overall, with climbs that can be long and steep. Requires good stamina if you do not opt for an electric bike.
⚡ To fully enjoy the route, even on the climbs, you can opt for an electric bike.
DAILY DISTANCES:
ELEVATION GAIN:
TYPE OF PATHS:
Most of the time, you will be riding along small country roads with light to zero traffic. Over 80% of the route is paved, the rest is well-maintained compact gravel. Tyres that are too thin, such as those on road racing bikes, should be avoided. No technical difficulties to report.
💡
Our trips prioritise discovery and relaxation over exertion.
We strive to adjust the length of the stages according to the terrain, the type of paths, and points of interest, so that each day remains balanced, enjoyable, and open to the unexpected.
We also attach great importance to avoiding roads with heavy traffic as much as possible, in order to offer, ultimately, a quiet and safe route.
PRACTICAL INFORMATION
⏱️ DURATION
7 days and 6 nights, including arrival and departure days. 5 days of cycling.
📅 POSSIBLE DEPARTURE DAYS
Every Saturday, from late March to mid-October
🗺️ ROUTE TYPE
Linear.
📍 START AND END POINT
Start of the trip: Pisa
End of the trip: Florence
🌦️ WHEN TO GO?
The weather is generally favourable from late March to October.
The best season to explore Tuscany by bike is from April to June and from September to October. It is also possible in July-August, but it can get very hot!
In spring, temperatures are ideal, the sun is generally already out, and nature is in full bloom. In summer, the Mediterranean influence is at its peak, and the sun generally reigns supreme. Late summer/early autumn is also a very good time to visit.
🍽️ MEALS
Breakfasts are included.
Lunches and dinners are at your own discretion.
During the day, you can grab a bite in local restaurants or have a picnic by picking up supplies at supermarkets.
For dinner, there will always be several restaurants within walking distance of your accommodation… unless the hotel has one itself!
🧳 LUGGAGE TRANSFER
Your luggage is transported from one accommodation to the next by one of our partners. You only carry your personal items for the day during the cycling stages. A pannier is provided with the rental bike.
🚩 ARRIVAL
BY TRAIN
There are direct TGV trains to Turin from Brussels, Paris, or Lyon. A local train (Trenitalia) will then take you to Pisa. Please note that in Turin, you must change stations from Torino Porta Susa to Torino Porta Nuova (about a 20-minute walk or 5 minutes by metro). More information: https://www.sncf-connect.com/ and: https://www.trenitalia.com/fr.html
BY PLANE
Many airlines serve the airports of Pisa and Florence from all over Europe.
BY CAR
Allow 4 to 4.5 hours of driving to Pisa from the south-east border of France.
📑 TRAVEL DOCUMENTS
To ensure you get the most out of your adventure, we will provide you with various practical and easy-to-use materials:
A roadbook (A5 booklet) written by us, including:
- Practical information
- A description of the route
- All necessary tourist information
- Cultural facts and anecdotes
Our navigation app (with your GPS tracks)
- User-friendly app (a short tutorial will be sent to you just in case)
- Satellite navigation (works in flight mode)
- Customised tracks between each accommodation
- Voice guidance
📞 INDEPENDENCE AND ASSISTANCE
You are travelling independently (self-guided), with 7/7 telephone assistance in case of any issues.
🛡️ INSURANCE
To guarantee reimbursement of costs in case of trip cancellation or problems on-site, you can take out cancellation insurance (CAP Explorer Cancellation) or assistance insurance (CAP Explorer Assistance). Find out more about insurance.
🎒 GEAR TO BRING
A helmet, a lock, a repair kit, a phone mount, and a waterproof rear pannier constitute the basic equipment. If you have rented a bike, these are included (the helmet is only upon request).
For added comfort, we recommend that you also bring the following specific accessories:
Waterproof over-trousers
Lightweight, waterproof, windproof, and easy to put on, they protect against rain, splashing water, and mud. Some models have gaiters that also cover your shoes.
Power bank
Useful for recharging your phone during your lunch break: navigation is battery-intensive, even in flight mode. Recommended unless your battery is very high-performing.
Expect to pay £10-£20.
Cycling shorts or gel saddle cover
Padded shorts improve comfort by absorbing shocks and reducing friction during long rides. Alternatively, opt for a padded saddle cover.
Water bottle
More practical and sustainable than disposable bottles. Some keep drinks cool for several hours thanks to double-walled insulation.
Buff / neck warmer / beanie
Outside of the summer, mornings can be chilly and you will not regret having packed them!
2026 PRICES
The price is calculated based on a room for 2 people. All rates are per person and subject to availability of the desired room type.
| Package | Low season | Mid season | High season |
|---|---|---|---|
| Double/twin room | €889 | €1,059 | €1,109 |
| Single room supplement | + €350 | + €350 | + €350 |
| Child discount (* in the same room as 2 full-paying adults) |
0-3 years: - 80% | 4-11 years: - 0% | 12-17 years: - 0% | ||
| Group discount | 6 - 11 pers.: - 5% | 12+ pers.: - 10% | ||
| Extra nights (optional) | Low season | Mid season | High season | |
|---|---|---|---|---|
| Pisa | Double/twin room | €75 | €75 | €75 |
| Single room | €130 | €130 | €130 | |
- Low season: 28/3 - 11/4 & 26/9 - 10/10
- Mid season: 12/4 - 8/5 & 5/9 - 25/9
- High season: 9/5 - 4/9
| BIKE RENTAL (equipment included) | |
|---|---|
| Electric bike | €305 |
| Trekking bike | €120 |
| Child bike (-12 years) | €120 |
THE BASE PRICE INCLUDES
- Hotel nights in the chosen comfort category
- Breakfasts at each accommodation
- Luggage transfer between accommodations
- Detailed PDF roadbook in Italian, French, or English, created by our partner
- GPS tracks of the route via our navigation app
- Luggage tags
- 7/7 telephone assistance
- Booking fees
OPTIONS
- Rental bike(s)
- Single room supplement
- Extra night(s) in Pisa
- Optional insurance: cancellation and/or assistance
THE PRICE DOES NOT INCLUDE
- Travel to/from Pisa
- Tourist taxes (€25-30/person)
- Meals not mentioned above
- Entrance fees to tourist sites and other personal expenses
- Anything not listed in "THE BASE PRICE INCLUDES"
SPECIAL CASES
- If you transport your own luggage, a discount is applied (see booking form). An extra pannier is provided if you rent a bike.
- Solo travellers: a logistics supplement is added to the single room supplement.
REVIEWS
Thierry and Pascale, 63 and 58 years old"Back from Tuscany where we had an excellent stay. Thanks to Cyclodyssées for this great organisation." September 2025
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