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Cycle Europe - serving bicycle travellers since 1972

Bicycle Tours — Italy

Classic Tuscany - Cycling from Florence to Pisa

Classic Self-Guided

The best way to explore one of Italy's most famous regions, Tuscany, is to cycle through it while enjoying the perfect blend of culture, cuisine, history, and rolling scenery. Tuscany is known for its earthy wines, rich art history, architecture, and its welcoming people. Walk through living history in the vibrant cities of Florence, Siena, San Gimignano, Pisa. From Piazza della Signoria in Florence to Piazza dei Miracoli in Pisa, through Siena, San Gimignano and Lucca. This bicycle tour starts at the heart of Tuscany, along the "wine route", where you'll see the production of Chianti and other wines. Enjoy a wine tasting in one the numerous wine cellars of this area. After Siena our bicycle tour continues to San Gimignano, famous for its adorning towers, and Lucca, known for the well-preserved Renaissance walls encircling its historic city center. Lastly, you'll visit Pisa and its leaning tower. Join us and experience Tuscany by bicycle.

2021 Early Bird Booking Discount available!
Book by May 15th, 2021 to receive €100 off per person.

Free premium bike rental!
Available on all departures through July 31st, 2021, the rental fee for our premium titanium-frame road or hybrid bikes is waived.


For more detailed tour information download the Tour Factsheet

Request space on this Bicycle Tour »

  • Day 1

    Arrive in Florence

    Highlights: Renaissance Florence, Uffizi Gallery

    Arrive in Florence today and take in the city's rich history and its beauty: climb up Giotto's tower for a stunning view of the city below and the Duomo in the skyline; visit the Uffizi Gallery, or walk the Ponte Vecchio bridge for a striking angle. We will meet in the afternoon for a tour briefing and bike fitting, and give you suggestions for dinner.

  • Day 2

    Florence to Radda in Chianti

    Highlights: The Chianti region

    As you leave Florence you?ll climb some of Chianti?s famous hills as you make your way to Radda, your home for the night. Stop in Greve for a short visit of the main square and the famous Macelleria Falorni, producer of local salumi. Radda is a delightful a small town and was an important junction for traveler's heading to north and south. Daily distance: 61 km (38 miles).

  • Day 3

    Cycle to Siena

    Highlights: Medieval town of Siena, Piazza del Campo

    Cycle the south part of the Chianti Region, then take the afternoon to explore Siena. Italy's best-preserved medieval city rivaled Florence for dominance in Tuscany during the 1300s. You'll be transported back in time as soon as you enter the city walls. Daily distance: 48-52 km (30-32.5 miles).

  • Day 4

    Ride to San Gimignano

    Highlights: The jewel village of Monteriggioni, San Gimignano

    Your bike ride today takes you into the heart of Tuscany. You will pedal past vineyards, 17th century villas, and small towns on your way to San Gimignano, one of the best-preserved medieval villages in Italy and designated a UNESCO World Heritage Site. San Gimignano is famous for its many towers, remnants from the 13th and 14th centuries. Daily Mileage: 50 km (31 miles).

  • Day 5

    From San Gimignano to Vinci

    Highlights: Olive groves and vineyards, Leonardo da Vinci's birthplace and museum

    Our ride takes you through rolling hills peppered with small towns along the way. Your final destination is Vinci, the birthplace of Leonardo da Vinci. Here you'll have a chance to visit the house where da Vinci was born and a museum with scale models of his inventions. Distance: 68 km (42 miles).

  • Day 6

    Bicycle to Lucca

    Highlights: Medici villa, bicycle countryside of Tuscany, 17th century wall

    Climb the stairway to the Medici villa in Cerreto Guidi today for a great view as you continue west to Lucca, where you'll stay the next two nights. Lucca was a Roman town and one of medieval Italy's most prosperous city-states. Today, Lucca retains its medieval charm with its small shops and sidewalk caf?s, as well as the beautiful 17th-century wall surrounding the town. Distance: 58 km (36 miles).

  • Day 7

    Loop ride to Pisa

    Highlights: Leaning Tower of Pisa, Piazza of Miracles, Lake Massaciuccoli

    Your last day of cycling takes you to Pisa where you can visit the Leaning Tower and the Piazza of Miracles. Our route to Pisa takes you by Lake Massaciuccoli, where Puccini wrote many of his operas. After a stroll through Pisa, head back to the less-touristy town of Lucca to enjoy an evening passeggiata along the main pedestrian way. Distance: 59-69 km (37-43 miles).

  • Day 8

    Tour ends

    Highlights: Arrivederci!

    After a breakfast buffet in your hotel, you're ready to continue your adventure wherever it may lead. We hope you have enjoyed cycling with us! Thanks for joining us and "buon viaggio"!

    PLEASE NOTE: The final itinerary, including hotels and/or activities described here, are subject to changes according to availability. City hotel taxes are not included.

Includes Includes: 7 nights in 3- and 4-star lodgings; all breakfasts; bike fitting and briefing in English by our professional staff at tour start; GPS device with pre-loaded navigation routes (one for every two cyclists); access to smartphone app with tracks and digital "roadbook"; printed roadbook with detailed daily information, maps and more; luggage transfers

Not Included: Travel to and from the tour start and end; bicycle rental (see Prices tab); entrance to museums or other activities; city hotel tax (2 to 5 euro per night per person, to be paid locally by traveler); Any meals or beverages not indicated as included.

Solo Traveler and Private Group departures available - please inquire.

Lodging Upgrade: Room upgrades are possible in some hotels - please inquire for prices and availability

Extra nights available upon request - please inquire about adding nights along the itinerary or before/after the tour.

- In Florence, extra hotel night: approx. 65 euro per person, depending on season and availability.
- In Lucca or Pisa, also available – 2021 rates coming soon.

PLEASE NOTE : The final itinerary, including hotels and/or activities described here, are subject to changes according to availability. City hotel taxes are not included.
Countries Italy
Begin/End Florence/Pisa
Arrive/Depart Florence Airport (FLR) / Pisa Galileo Galilei Airport (PSA)
Total Distance 348 - 352 km (217 - 220 miles)
Daily Distance 48 - 68 km (30 - 42 miles)
Rating 301
Notes Navigation and roadbook:
On our CLASSIC self-guided tours, detailed daily information and route navigation are provided through a GPS device (one included for every two cyclists), a smartphone application, as well as a printed roadbook with thorough daily descriptions and maps. Our app allows you to download the information into your smartphone, where you can the daily routes even in offline mode. Hotel itinerary, daily ride descriptions, cultural information, visit suggestions, elevation profiles, and emergency numbers are all stored in one organized place. Downloading maps and routes also allows you to navigate in offline mode. If you prefer, you can download the routes into your GPS device and print the detailed route notes before leaving home and use them on tour, or rely on the detailed roadbook that we will print for you and delivery before the tour start

For more information on the smartphone app, visit RideWithGPS Experiences.


Luggage transfers are included in your package.
The luggage is normally collected from 09.00 at the reception of the hotel and is delivered at the following hotel by 15.30. Every piece of luggage must be marked with a visible luggage tag. Please make sure yours have correct tags. If your luggage is not ready by the time the driver comes to collect it, you may have to pay a local taxi for the service.

Please consider that the luggage is not insured during the transport. You need to have your own insurance. Do not leave valuables or fragile items in your luggage.
Normally, the luggage transport service cannot be used by participants to skip the cycling stage. In case you need help to skip the cycling stage, please contact our emergency number and we will arrange it for you.
Terms Terms & Conditions
Dates Prices Single Supplement
Dates Available March 1 to October 31, 2021

Starts every Thursday *

* Other tour start days may be available, with a possible supplemental fee - please inquire. Please note that most museums in Florence are closed on Mondays, so we discourage starting tour on Mondays.

Per person price based on double occupancy with 2 participants per departure minimum; Single rooms and Solo Traveler departures available - see supplemental fees on the right.

2021 Early Bird Booking Discount available! Book by May 15th, 2021 to receive €100 off per person.

Free premium bike rental! Available on all departures through July 31st, 2021, the rental fee for our premium titanium-frame road or hybrid bikes is waived.

Group Discounts for 6 or more participants booking together on the same departure! Please inquire for details through our contact form below.


If you are looking for challenging cycling in Tuscany, our Bicycling Cortona, Montalcino and Siena in Southern Tuscany tour (8-day) can also be done back to back with this tour for a Grand Tour of Tuscany! Don't want to break sweat but still explore this amazing region? You can with our top-notch ebikes!


Bike Rental options:
We offer quality bikes in different styles, all great options for this bike tour. Our bikes are maintained and delivered in optimal working condition.

The prices below are per bike for the duration of the tour, including delivery to starting point in Florence and collection from ending point in Lucca.

Bike rental rates
Aluminum hybrid: €120
Premium Titanium road or hybrid: €160
E-bike (hybrid with straight handlebar): €240
Tandem: €280 (priced per bike, for 2 cyclists)
Tag-along or kid trailer: €80

For detailed specs and photos of our bikes, see our website - Bike Rentals Italy.

High-Season notes (May, September and early October):
Hotels: may be subject to availability, and a hotel supplemental fee may be applied.
Bike Availability: our premium (titanium-frame) bikes are also subject to availability.

Prices €1270 per person

2021 Early Bird Booking Discount available now!
Single Supplement €290 fee for private, double room

€800 solo traveler fee (only one person on departure)
Next Step Request space on this Bicycle Tour »
  • Really a great route and strong package of maps, etc were provided. It was a great experience and I look forward to another trip. Loved Radda.


    September 2018

  • "What was your favorite experience on this trip?" The cities we stopped in and the people we met. Family meal in Vinci especially pleasant

    Bob L.
    September 2018

  • The step by step directions were perfect. They were exactly on-spot and got us to our destinations. The hotels were great for the level we chose. We especially liked the hotel in San Gimignano with the balcony that overlooked the valley. Very nice! It all was wonderful. Of course the biking was the favorite, especially the routes out of Florence to Radda. Our tour advisor, Stefania, was outstanding! She created this special tour based on the dates and locations and sites we wanted to see. She gave us travel tips for cities that were before and after our tour. She gave recommendations for guided tours in Florence that was outstanding. She earned our confidence in your company as we planned the details together many months in advance. The bikes, the route and the hotels were perfect. The luggage arrived just as planned each day. The weather was even perfect! Thank you Stefania!

    Brent P.
    Utah, USA
    May 2017