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Highlights
Cycle from Florence to Pisa: art, wine, history, and stunning landscapes in 8 days.
Explore Florence's iconic art and history, from the Uffizi Gallery to the Duomo and Ponte Vecchio.
Pedal past vineyards and olive groves, stopping at charming towns like Greve and Radda in Chianti.
Immerse yourself in Siena's rich history as you explore its stunning piazzas and ancient streets.
End your tour with a visit to Pisa's famous tower and a bike ride around Lucca's well-preserved medieval walls.
Explore the heart of Tuscany on a cycling adventure through its rolling hills, charming towns, and rich cultural heritage. The Tuscany Cycling Tour takes you from the Renaissance wonders of Florence to the iconic Leaning Tower of Pisa, with stops in historic cities like Siena, San Gimignano, and Lucca. Pedal through the famous Chianti wine region, visit local wineries, and discover the beauty of medieval villages and picturesque landscapes.
This 8-day cycling journey is the perfect way to immerse yourself in Tuscany’s art, cuisine, and history. Cycle through vineyards, olive groves, and Renaissance walls, while experiencing Tuscany’s warm hospitality. Don’t miss out on this unforgettable exploration of Tuscany by bicycle!
Explore the heart of Tuscany on a cycling adventure through its rolling hills, charming towns, and rich cultural heritage. The Tuscany Cycling Tour takes you from the Renaissance wonders of Florence to the iconic Leaning Tower of Pisa, with stops in historic cities like Siena, San Gimignano, and Lucca. Pedal through the famous Chianti wine region, visit local wineries, and discover the beauty of medieval villages and picturesque landscapes.
This 8-day cycling journey is the perfect way to immerse yourself in Tuscany’s art, cuisine, and history. Cycle through vineyards, olive groves, and Renaissance walls, while experiencing Tuscany’s warm hospitality. Don’t miss out on this unforgettable exploration of Tuscany by bicycle!
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Florence to Pisa Self-Guided Cycling Tour Itinerary
Day 1 Arrival in Florence
Upon arrival in Florence, immerse yourself in the city’s rich history and beauty. Start your day by climbing Giotto’s Tower for a breathtaking view of the city below, with the Duomo framing the skyline. Explore the renowned Uffizi Gallery, or take a leisurely stroll across the iconic Ponte Vecchio bridge to enjoy unique views of the city. In the afternoon, meet for a tour briefing and bike fitting, followed by personalized suggestions for dinner to start your Tuscan adventure.
Overnight Location: Hotel in Florence
Distance: N/A
Meals: N/A
Day 2 Florence to Radda in Chianti
Depart Florence and begin your ascent through some of Chianti’s iconic hills, heading toward Radda in Chianti, where you’ll spend the night. Along the way, stop in the charming town of Greve to explore the main square and visit the famous Macelleria Falorni, renowned for its local salumi (cold cuts). Radda, a quaint and historic town, was once a key crossroads for travelers journeying north and south through Tuscany.
Overnight Location: Hotel in Chianti
Distance: 61km, 1,273m / 4176ft elevation gain
Meals: Breakfast
Day 3 Cycle to Siena
Pedal through the southern part of the Chianti Region, then spend the afternoon discovering Siena. Known as Italy’s best-preserved medieval city, Siena once rivaled Florence for power and influence in Tuscany during the 1300s. As you step inside its ancient city walls, you’ll feel as though you’ve traveled back in time.
Overnight Location: Hotel in Siena
Distance: 51km, 957m / 3,140ft elevation gain
Meals: Breakfast
Day 4 Ride to San Gimignano
Today’s ride takes you deep into the heart of Tuscany, cycling past vineyards, 17th-century villas, and charming small towns. Your destination is San Gimignano, a UNESCO World Heritage Site known for its well-preserved medieval architecture. Famous for its striking towers, remnants of the 13th and 14th centuries, San Gimignano offers a glimpse into Tuscany’s rich history.
Overnight Location: Hotel in San Gimignano
Distance: 52km (32 miles), 895m / 2,936ft elevation gain
Meals: Breakfast
Day 5 From San Gimignano to Vinci
Today’s ride takes you through rolling hills, dotted with picturesque small towns. Your journey ends in Vinci, the birthplace of the renowned Leonardo da Vinci. Here, you’ll have the opportunity to visit his childhood home and explore a museum featuring scale models of his groundbreaking inventions.
Overnight Location: Agriturismo in Vinci
Distance: 72km (45 miles), 1021m / 3,050ft elevation gain
Meals: Breakfast
Day 6 Bicycle to Lucca
Climb the stairs to the Medici villa in Cerreto Guidi for stunning panoramic views, then continue your ride west to Lucca, where you’ll stay for the next two nights. Once a prosperous Roman town and medieval city-state, Lucca still preserves its charm with quaint shops, sidewalk cafés, and a beautifully intact 17th-century city wall.
Overnight Location: Hotel in Lucca
Distance: 59km, 439m/ 1,440ft elevation gain
Meals: Breakfast
Day 7 Loop ride to Pisa
On the final day of cycling, ride to Pisa to visit the iconic Leaning Tower and the Piazza dei Miracoli — arriving by bike adds to the excitement! Along the way, pass by Lake Massaciuccoli, where Puccini composed many of his famous operas. After exploring Pisa, return to Lucca for a relaxing evening “passeggiata” along the pedestrian streets or wander through its charming alleys and piazzas.
Choose from three options for your ride: cycle to Pisa and return by train (with your bike onboard), take a longer loop through scenic Tuscan hills, vineyards, and grand villas, or challenge yourself with an extended ride to the Tuscan coast to dip your toes in the Tyrrhenian Sea.
Overnight Location: Hotel in Lucca
Distance: Varies depending on the option selected.
Meals: Breakfast
Day 8 Departure
After enjoying a delicious breakfast buffet at your hotel, you’re free to continue your adventure wherever it may take you. We hope you’ve had a memorable time cycling through Tuscany and exploring its rich history, culture, and landscapes. Thank you for joining us on this unforgettable journey. “Buon viaggio!”
Overnight Location: N/A
Distance: N/A
Meals: Breakfast
2026 Pricing for Florence to Pisa Self-Guided Cycling Tour The departures are available starting every Friday from March 1st through October 31st, 2026.
The starting price for two people sharing a double or twin room is EUR2335 per person.
An aluminum bike rental is EUR175, and an e-bike is EUR270.
Accommodation on Florence to Pisa Self-Guided Cycling Tour
This tour is based in Hotels. Hotels on this trip are 3 and 4-star and offer modern conveniences that can make this trip more pleasant. Rooms may include amenities such as a minibar, concierge service, and a spa.
Single Rooms and Solo Travellers
Rooms are based on double occupancy. A single supplement is available for a private room when possible. Solo travelers may need to pay an additional fee.
What’s Included in the Florence to Pisa Self-Guided Cycling Tour?
Meals
7 breakfasts are included.
Accommodations
Accommodations for 7 nights are included. Additional nights before the tour and after the tour are not included but can be added as a supplement.
Transportation during the Tour
Luggage transfers are included throughout the tour.
Also included
- Route Information that can be accessed through digital mobile app
- Bike fitting and briefing in English by our professional staff at tour start
Not included
- Flights
- Bicycle rental
- Meals, drinks, or snacks not previously mentioned
- Gratuities for tour guides or other staff if desired
- Entrance to museums or other activities not indicated as included
- City hotel tax
- Insurance
Optional Extras
- Additional nights before or after the tour
- Single occupancy upgrades
- Guided visit of Florence
- Guided visit of Siena
- Cooking Classes
- Dinner in Vinci
- Wine tasting in Vinci (closed on Monday)
- GPS rental
- Printed roadbook
- Bike Rental
- How hard is the Florence to Pisa Self-Guided Cycling Tour?
- Do I need a visa to travel to Italy?
- Are meals included on the Florence to Pisa Self-Guided Cycling Tour?
- Do I need insurance?
- How do I get to Florence to start this tour?
- Is the Florence to Pisa Self-Guided Cycling Tour in English?
- Where does the Florence to Pisa Self-Guided Cycling Tour end?
- Do I need special vaccines to travel to Italy?
- Are there any travel restrictions for Italy?
The Florence to Pisa Self-Guided Cycling Tour is rated at level 2/5, making it suitable for cyclists with some experience. The route is mostly hilly with a few good climbs, and you can expect an average daily elevation gain of about 800m (2600 feet). The terrain includes some unpaved country roads, adding variety to the ride. Overall, it’s a challenging yet enjoyable adventure for those looking to explore Tuscany by bike.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
7 breakfasts are included.
Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover cycling. Get your travel insurance.
To start the Florence to Pisa Self-Guided Cycling Tour, we recommend flying into Florence Airport (FLR). Alternatively, you can fly into Pisa Galileo Galilei Airport (PSA), which is about 30 minutes away from Florence's main train station, Firenze S. Maria Novella. From there, you can catch a shuttle bus or take a regular bus. If you prefer a taxi, be sure to agree on a fare before accepting the ride, as it takes around 15 to 20 minutes, depending on traffic.
For self-guided tours, the meeting time is typically set between 2pm and 4pm. We suggest planning your travel to ensure plenty of time to reach the meeting location.
This is a self-guided tour without guide services, but all tour materials are provided in English.
Your tour concludes in Lucca.
Check with your family doctor.
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
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