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Cycle Europe - serving bicycle travellers since 1972

Bicycle Tours — Italy

Classic Tuscany - Cycling Florence to Pisa

Classic Self-Guided - Florence to Pisa - 8 days

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.

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.

    Accommodation: Hotel Silla, or similar.

  • Day 2

    Florence to Radda in Chianti

    Highlights: The Chianti region

    As you leave Florence you will climb some of Chianti's famous hills, on your way to Radda in Chianti, your home for the night. Stop in Greve for a visit of the main square and the famous Macelleria Falorni, producer of local salumi (cold cuts). Radda is a delightful a small town and was historically an important junction for traveler's heading to north and south.

    Daily distance: 61 km (38 miles)
    Elevation gain: +1273m (4176ft)

    Accommodation: Hotel San Niccolo, or similar.

  • 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: 51km (31 miles).
    Elevation gain: +957m (3140ft).

    Accommodations: Hotel Il Chiostro del Carmine, or similar.

  • 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 distance: 50 km (31 miles).
    Elevation gain: + 774m (2540ft).

    Accommodation: Hotel Leon Bianco, or similar.

  • 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.

    Daily distance: 74 km (46 miles).
    Elevation gain: + 936m (3070ft).

    Accommodation: Agriturismo il Piastrino, or similar.

  • 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 cafes, as well as the beautiful 17th-century wall surrounding the town.

    Daily distance: 59 km (36 miles).
    Elevation gain: + 439m (1440ft).

    Accommodation: Hotel La Luna, or similar.

  • 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 (arriving there by bike is a grand experience!). Our route to Pisa takes you by Lake Massaciuccoli, where Puccini wrote many of his operas. After a stroll through Pisa, head back to Lucca to enjoy an evening "passeggiata" along the main pedestrian way, or explore its countless amazing alleys and piazzas.

    Two options for your ride today - cycle to Pisa and return by train (with bike aboard). Or a longer loop ride, through lovely Tuscan hills, vineyards and stately villas.

    Short option: 31 km (19 miles), with + 143m (470ft) elevation gain.
    Long option: 72 km (45 miles), with + 460m (1509ft) elevation gain.

    Accommodation: Hotel La Luna, or similar.

  • 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
Access to smartphone app with tracks and digital roadbook
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
Any type of insurance (medical, trip cancellation and interruption, baggage, bike rental)

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: If you'd like to add nights before or after the tour, please inquire - we will be happy to provide a quote and add the nights to your tour package.

Extra meals & activities: (please inquire for price and availability)

  • Cooking classes available in various tour locations! Organized by Le Cesarine, experts in Italian culinary experiences. You will be hosted by a local at their home - your "Cesarina" - in a class that lasts about three hours, during which you will help the Cesarina prepare three courses. In the fourth and final hour, you will enjoy the meal (lunch or dinner) which you prepared during the class. Water and one bottle of house wine for every 3 people are included.

  • More options available:
  • Guided visit of Florence
    Guided visit of Siena
    Wine tasting in Vinci (closed on Monday)
    Dinner in Vinci

    Navigation and roadbook:
    On our self-guided tours, detailed tour information and route navigation tracks are provided through the free smartphone app Ride With GPS - our "digital roadbook" - which includes daily routes, maps, elevation profiles, and ride descriptions; schedules and hotel itinerary; cultural and sightseeing information, visit suggestions; emergency numbers and more, all stored in one organized, easy to use app. Downloading the app content also allows for offline mode navigation. Participants can also upload the routes to their own GPS device, and even print the detailed route notes before leaving home

    On our self-guided tours, GPS device rental, as well as a printed roadbook, are available at an optional extra fee:
  • GPS device rental: €50
  • Printed roadbook: €45 (second copy of printed roadbook €15)

  • For more information on our navigation options, as well as the smartphone app, please read our blog: What's it like to navigate on our self-guided tours?.

    Luggage transfers
    Luggage transfers are included in your package. The luggage is normally collected from 09.30 at the reception of the hotel and is delivered at the following hotel by 15.00 hrs. Please use the luggage tags provided by Cycle Europe on all your luggage being transferred. Please have your luggage ready before the driver comes to collect it, otherwise 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.

    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.

    Tour code: itbs3564
    Countries Italy
    Begin/End Florence/Pisa
    Arrive/Depart Starting point: Hotel Silla - Via de' Renai, 5, Firenze
    We recommend flying into Florence Airport (FLR) , but you can also fly into Pisa Galileo Galilei Airport (PSA)
  • It’s a 30-minute trip from the airport to Florence’s main train station Firenze S. Maria Novella. You can catch a shuttle bus, or take a bus
  • If you'd rather take a taxi, agree on a fare before accepting the ride. It takes about 15/20 minutes, depending on the traffic

  • The meeting time for our self-guided tours is typically set between 2pm and 4pm. We recommend travelers plan accordingly allowing plenty of time to arrive at the determined meeting place. Please note a late fee may be applied for late arrivals - please see our terms page for details

    Ending point: Hotel La Luna - Via Fillungo, Corte Compagni, 12, Lucca
    We recommend flying out of Pisa Galileo Galilei Airport (PSA), but you can also fly out of Florence (FLR), Rome Fiumicino (FCO), or other Italian airports

    Airport transfers:
  • Taxis from Lucca to the Pisa airport take about 45 minutes
  • From the hotel, take a taxi (5-minute ride) to the Lucca train station. Pisa International Airport Galileo Galilei is 45 minutes away: once you arrive in Pisa centrale train station, you will find the PisaMover monorail to get to the Airport in 5 minutes

  • Private airport transfers available if you prefer to be driven from airport to hotel in a private vehicle transfer, please inquire for cost - we will be happy to include this service in your tour package

    Final arrival and departure instructions along with other detailed pre-travel documents, will be e-mailed prior to your travel, with information specific to your departure (including the actual hotels used on your tour dates, which may vary from the hotels listed above.)

    Total Distance 348 - 352 km (217 - 220 miles)
    Daily Distance 48-68 km (30-42 miles)

    Difficulty description: Mostly hilly with some good climbs, average daily elevation gain of about 500m (1500 feet). Few unpaved country roads.
    Rating 301
    Terms Terms & Conditions
    Dates Prices Single Supplement
    Dates This tour is available from March 1 to October 31

    * 2024 price, per person based on double occupancy; minimum 2 participants per departure.

    Starts every Friday. Other start days available by request (extra fee applies). Please note that starting on certain days of the week will make some visits (such as museums or tastings) impossible. Most museums in Florence are closed on Mondays, so we discourage starting tour the previous Monday.

    Solo traveler departures are also available (only one person on the departure), with a supplemental fee of €845. This fee includes the cost of the single/double room supplement, as well as a GPS unit with the pre-loaded routes.

    Group Discounts are available for 4 or more participants booking together on the same departure! Please inquire for details through our contact form below.

    For more ways to save, see our Discounts and Promotions page (hint - consider coming in the low-season!)


    High-Season surcharge (May, June, September and early October): a €100 per person surcharge is applied on high-season departures. If joining an existing, confirmed departure date, the fee may be waived - please inquire.

    2024 Confirmed departure dates:

    October 11

    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: €130
    Premium Titanium road or hybrid: €170
    E-bike (hybrid with straight handlebar): €255
    Tandem: €295 (priced per bike, for 2 cyclists)
    Tag-along or kid trailer: €80

    Bike rental insurance is available for purchase with all our rental bikes – see details in the Bike Rental Insurance section of our Terms and Conditions page.

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


    If you are looking for challenging cycling in Tuscany, our Postcard 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 a sweat but still explore this amazing region? You can with our top-notch ebikes!

    Additional useful information:

    • Do you have any questions about how our bike tours work? Check out our FAQs page!

    • Curious about the difference between our Casual and Classic self-guided tours? Check out our introduction blog on Casual Self-Guided Tours.

    • We offer various tools for navigation - this page details what it's like to navigate on our self-guided tours.

    • If the self-guided formula isn't right for you, check out this blog introducing the differences between Guided and Self-Guided Tours.
    Prices €1425 per person *
    Single Supplement €315 fee (in double room for single use)
    Next Step Request space on this Bicycle Tour »
    • This particular tour is for reals. It is not for anyone who hasn’t specifically trained to do 40 miles and 3000 feet of climbing day after day. But if you are a serious cyclist, it is great. We got to see so much of the countryside and stay in cool towns we likely never would have. Radda, San Gimignano, and Lucca were particularly good. It was fun to ride through the city gates, get food and drinks, and do a little shopping each day (not much in Radda).

      Becky J.

    • We wanted a trip in Tuscany that would allow us to balance riding and touristing. We also needed a route that would be challenging for two cyclists and acheivable for one on an eBike. We didn't realize how good the RideWithGPS information and maps would be. As soon as we saw them, we realized the printed roadbook is completely unnecessary and I think they could be completely removed. Everything was spectacular. The hotels are great, the routes are great, and the service made the whole trip easy. This was one of our best vacations. Everything that Cycle Europe provided worked great and made it an easy trip, so we could simply enjoy ourselves.

      Jeff B.

    • 10 out of 10: We really appreciated Sara Lettereli's help throughout planning, orientation, and the trip itself. (Our favorite part was) experiencing the culture of Tuscany and its people and rich history, architecture, art, agriculture, landscape and food

      Tom H., USA, 2021

    • 10 out of 10: Excellent customer service. We started out working with a few different outfits, but Sara Letterelli was by far the most responsive contact we had. She was able to meet all of our picky requests and kept us informed throughout the whole process. Beautiful scenery and fun cycling. Thank you for a most wonderful and memorable trip!

      David M., USA, 2022

    • 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