Grand Tour of Tuscany – Pisa – Siena – Florence

Tuscany Cycling Tour – From Pisa to Florence

Discover the beauty of Tuscany on a spectacular cycling journey through rolling hills, vineyards, olive groves and picturesque medieval villages. Ride through the famous landscapes of Chianti and Val d’Elsa, with routes leading to historic places such as Gaiole in Chianti, San Gimignano and Monteriggioni. Along the way, enjoy authentic Tuscan cuisine, local wines and the region’s extraordinary cultural heritage. Your Grand Tour of Tuscany begins in Pisa and ends in Florence, surrounded by the timeless beauty of the Italian countryside.

Highlights

• Cycle through the rolling hills and vineyards of Chianti and Val d’Elsa
• Discover medieval villages including Gaiole in Chianti, San Gimignano and Monteriggioni
• Enjoy Tuscan wines, regional cuisine and gourmet breaks
• Experience Florence and its magnificent Renaissance heritage
• Start in Pisa and finish in Florence on an unforgettable Tuscany cycling tour

Day 1 – Pisa

Arrive individually in Pisa and spend the night in this fascinating Tuscan city. Pisa is world-famous for the Piazza dei Miracoli, home to the iconic Leaning Tower, the cathedral’s remarkable bell tower. A UNESCO World Heritage Site since 1987, Pisa combines impressive monuments with the lively and welcoming atmosphere of a historic university city.

Accommodation: Hotel

Day 2 – Pisa to Casciana Terme

Begin your Tuscany cycling tour along the River Arno, riding towards Pontedera, a modern Tuscan town known for its connection to the wine producer Castellani and the renowned Amedei chocolate company. Continue through peaceful olive groves and vineyards as the landscape becomes increasingly rural and picturesque. Your destination is Casciana Terme, a charming spa town with ancient Etruscan roots. Its thermal springs are traditionally associated with Countess Matilda of Tuscany and have attracted visitors for centuries.

Accommodation: Hotel
Meals: Breakfast
Cycling: 50 km
Elevation gain: +290 m / -180 m

Day 3 – Casciana Terme to San Gimignano / Colle Val d’Elsa

Follow the historic Via Francigena through vineyards, olive groves and the rolling hills of Tuscany on your way to magnificent San Gimignano. Perched on a hilltop and surrounded by medieval walls, this UNESCO World Heritage town is famous for its impressive medieval towers and beautifully preserved historic centre. Take time to explore its charming streets before enjoying authentic Tuscan cuisine in the evening. Depending on availability, your overnight stay may be in Colle Val d’Elsa instead.

Accommodation: Hotel
Meals: Breakfast
Cycling: 50 km
Elevation gain: +755 m / -545 m

Alternative from Colle Val d’Elsa: 70 km, +1,000 m / -980 m

Day 4 – San Gimignano / Colle Val d’Elsa to Siena

Continue along ancient sections of the Via Francigena, surrounded by classic Tuscan scenery. Enjoy views of Mount Maggio before reaching the impressive medieval castle of Monteriggioni, famously mentioned by Dante in his literary works. From here, continue towards Siena, one of Tuscany’s most beautiful historic cities. Its distinctive red-brick buildings and the towering Torre del Mangia create an unforgettable skyline.

If your stage starts in Colle Val d’Elsa, the cycling distance is approximately 25 km.

Accommodation: Hotel
Meals: Breakfast
Cycling: 45 km
Elevation gain: +740 m / -675 m

From Colle Val d’Elsa: 25 km, +445 m / -242 m

Day 5 – Siena to Greve in Chianti

Today you enter the heart of the famous Chianti wine region. Your first stop is Castagnoli, where you can admire Brolio Castle, historic home of the Ricasoli family and now associated with one of the region’s renowned wine estates. Continue through the vineyards and green hills to Radda in Chianti, a classic Tuscan village surrounded by beautiful countryside and traces of its Etruscan past.

The route then leads to Panzano in Chianti before continuing to Greve in Chianti, one of the region’s best-known wine towns. Every September, Greve hosts the famous Chianti Classico Wine Festival. Take the opportunity to sample some of the area’s celebrated wines and experience the authentic flavours of Tuscany.

Accommodation: Hotel
Meals: Breakfast
Cycling: 55 km
Elevation gain: +935 m / -1,045 m

Day 6 – Greve in Chianti to Florence

Your final day of cycling takes you through some of the most iconic landscapes of Tuscany and Chianti. Ride towards the small village of Mugnana and its historic castle before continuing to Grassina, traditionally known as the Village of the Washerwomen, where Florentine aristocratic families once had their laundry washed.

A few kilometres before Florence, stop at La Fonte della Fata Morgana, a historic spring associated with the legendary Fata Morgana. Continue along quiet country roads, passing fields and tree-lined avenues, until you reach the River Arno. Follow the river into the heart of Florence, the magnificent capital of the Renaissance and the final destination of your Tuscany cycling adventure.

Accommodation: Hotel
Meals: Breakfast
Cycling: 40 km
Elevation gain: +670 m / -850 m

Day 7 – Florence

Enjoy a final morning in Florence, surrounded by the extraordinary art, architecture and history of the Renaissance. After breakfast, your Tuscany cycling adventure comes to an end. Individual departure from Florence.

Meals: Breakfast

Accommodation

You will stay in carefully selected 3- and 4-star hotels throughout the tour. All rooms feature private en-suite bathrooms and air conditioning, providing a comfortable base after each day of cycling.

Bikes

Choose from comfortable and reliable rental bikes, designed and maintained specifically for cycling tours. Bike rental includes insurance against theft and irreparable damage. Each bike is professionally assembled and checked by mechanics at the main headquarters or the nearest operations base.

Available bikes:

• Touring Bike: 27-speed Shimano Deore, available with unisex or men’s frame
• E-bike: 9-speed Shimano, unisex frame

Bike features:

• Aluminium frame
• Mudguards
• Rear luggage rack
• Selle Royal comfort gel saddle
• Puncture-resistant Schwalbe tyres
• Ergonomic grips
• Speedlifter height-adjustment system

Bike Equipment

All rented adult bikes are equipped with practical accessories for a comfortable and safe cycling experience:

• 1 Ortlieb single-sided pannier per bike
• 1 front handlebar bag per room
• 1 repair kit per room, including a spare inner tube, glue, patches, pump, two Allen keys and tyre levers
• 1 combination bike lock per bike

Helmets

Helmets can be rented when booking. They are suitable for head circumferences of 58–61 cm and comply with the DIN EN 1078 (CE) European safety standard.

Important Notes

We recommend bringing your own reusable water bottle. It is a practical and sustainable choice for your cycling holiday.

To follow the tour smoothly using the Girolibero App, we also recommend bringing a mobile phone holder for your bicycle. This allows you to keep the route easily visible while cycling.

Route Profile

The tour combines scenic country roads, rolling Tuscan hills and a few sections on well-maintained unpaved roads. The daily stages vary in difficulty, with the most demanding climbs concentrated around Chianti.

Day 2 – Pisa to Casciana Terme
50 km | +290 m / -180 m

The easiest stage of the tour, making it an ideal introduction to cycling in Tuscany. The route includes some unpaved sections along the River Arno and follows the River Era on a towpath after Pontedera. Take extra care when cycling through traffic entering Pontedera.

Day 3 – Casciana Terme to San Gimignano / Colle Val d’Elsa
50–70 km | San Gimignano: +755 m / -545 m | Colle Val d’Elsa: +1,000 m / -980 m

The route is entirely on asphalt, with the elevation profile becoming more demanding after La Sterza. The alternative finish in Colle Val d’Elsa involves a longer and more challenging stage.

Day 4 – San Gimignano / Colle Val d’Elsa to Siena
45 / 25 km | from San Gimignano: +740 m / -675 m | from Colle Val d’Elsa: +445 m / -242 m

Mostly asphalt roads with some sections on good-quality unpaved roads before and after Poggibonsi, after Colle Val d’Elsa and near Monteriggioni. From San Gimignano to Colle Val d’Elsa, an alternative route can shorten the stage by approximately 10 km.

Day 5 – Siena to Greve in Chianti
55 km | +935 m / -1,045 m

A challenging stage through the heart of the Chianti wine region, with the entire route following paved roads and featuring numerous climbs and descents. An optional 15 km detour takes you to Gaiole in Chianti, adding approximately +380 m / -205 m of elevation.

Day 6 – Greve in Chianti to Florence
40 km | +670 m / -850 m

The final cycling stage follows paved roads through the beautiful Tuscan countryside. Despite the shorter distance, the route includes several climbs before the descent towards Florence and the River Arno.

What Awaits You

Level: Medium
Total distance: 240 km
Shorter version: 230 km
Terrain: 95% paved roads, 5% unpaved roads
Train connection between overnight stays: No
Option to shorten the itinerary by train: Day 2

This Tuscany cycling holiday is designed for regular cyclists who are in good physical condition. The daily stages average around 45 km and lead through classic Tuscan landscapes with numerous climbs and descents, including some more demanding uphill sections.

The reward is an unforgettable journey through vineyards, olive groves, medieval villages and the rolling hills of Tuscany, connecting Pisa, San Gimignano, Siena, Chianti and Florence.

Itinerary Changes

For organisational reasons, weather conditions or instructions from local authorities, the itinerary may be subject to changes before or during your holiday. Temporary route deviations, for example due to roadworks, may occur without prior notice. In such cases, please follow the local signs and instructions provided on site.

Special Diets

If you are vegetarian or vegan, gluten-intolerant, allergic to specific ingredients or substances, or have any other dietary requirements, please inform us at the time of booking. We will pass this information on to the hotels, although we cannot guarantee that every dietary request can always be accommodated.

Certain products, such as gluten-free food, may not always be readily available along the route. We therefore recommend bringing suitable snacks with you as a precaution.

Travel Insurance

We strongly recommend taking out appropriate travel insurance covering cancellation or interruption of your tour, accidents, and loss of or damage to luggage. We also recommend insurance covering any costs associated with medical assistance and repatriation.

Travel insurance is not included in the tour package.

Departure Dates

27 March – 9 October 2027

Special departure dates are available for groups of at least 6 people.

Prices – GOLD

Prices per person in €

Seasonal Supplements

Extra Nights in Pisa

Bike Rental

• Touring bike: €120
• E-bike: €290
• Helmet rental: €15

Note: The base tour price does not include bike rental, e-bike rental or helmet rental.

• • Iconic Tuscan Horizons: Cycle through rolling hills, ancient vineyards, and historic olive groves, connecting the world-famous landmarks of Pisa, Siena, and Florence on an unforgettable journey.
  • Tailored Riding Styles: Choose between a traditional road bike for an active athletic challenge or a premium e-bike for a smooth, relaxed glide up Tuscany’s iconic panoramic hillsides.
  • Cultural & Culinary Immersive: Experience Renaissance architecture, medieval hilltop fortresses, and authentic local trattorias featuring regional Chianti wines and world-class olive oils.