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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.

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  • 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).

    Accommodation Hotel Santa Caterina, 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 mileage: 50 km (31 miles).
    Elevation gain: + 774m (2540ft).

    Accommodation Hotel Bel Soggiorno, 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 Hotel Monnalisa, 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 caf?s, 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; 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

Private transfers (please inquire for price and availability)
Florence airport - Florence
Lucca - Pisa airport
Lucca – Florence airport

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.

Extra meals and activities (please inquire about price and availability):

Day 1 - Dinner in Florence
Day 2 – Snack at local shop (1 glass of wine, local cold cuts and cheeses)
Day 3 – Dinner in Siena
Day 3 – Guided visit of Siena
Day 4 - Dinner in S. Gimignano
Day 5 – Wine tasting in Vinci (closed on Monday)
Day 6 – Dinner in Lucca

Cooking class* available in more than one location along the way. You will be hosted by a local cook - your "Cesarina" - at their home in a class during which you will help the Cesarina prepare a whole meal. At the end of the class, you will enjoy the meal (3-course lunch or dinner) which you prepared.
*Inquire for prices.


Navigation and roadbook:
On our CLASSIC self-guided tours, detailed tour information and route navigation tracks 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 "digital roadbook" is delivered to tour participants via the Ride With GPS app, accessed on a smartphone - daily maps, elevation profiles, routes 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; or rely completely on the detailed roadbook that we will print for you and deliver at tour start

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 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.

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 How to get there and away:
Florence Airport (FLR) / Pisa Galileo Galilei Airport (PSA)

Starting point: Hotel Silla - Via de' Renai 5, Firenze
- We recommend flying into Florence Airport (FLR) , but you can also fly into Pisa
- 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 “Vola in Bus”which departs every hour from 6:30 am to 11:30 pm (one-way ticket: €6; round trip ticket: €10)
- If you'd rather take a taxi, agree on a fare before accepting the ride (expect to pay about €20/25 plus the cost of the luggage, € 1/piece). It takes about 15/20 minutes, depending on the traffic

Ending point: Hotel La Luna- > Via Fillungo, Corte Compagni 12, Lucca
- We recommend flying out of Pisa Airport, but you can also fly out of Florence or other Italian airports

Airport transfers:
- Taxis from Lucca to the Pisa airport cost about €60/70 and take about 45 minutes
- From the hotel, take a taxi (5-minute ride) to the Lucca train station (about €10). 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 (€5 one way)

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.)

* the hotels and prices listed above are for reference only and are subject to change (based on availability and seasonality)
Total Distance 348 - 352 km (217 - 220 miles)
Daily Distance 48 - 68 km (30 - 42 miles)
Rating 301
Terms Terms & Conditions
Dates Prices Single Supplement
Dates Available March 1 to October 31, 2022

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.

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.

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

Please inquire about possible discounts when joining one of the following 2022 confirmed departures (pending hotel availability):
May 14
June 3, 9
July 3
September 29

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 supplement (May-June, September and early October): Hotels and/or bikes may be subject to availability, and a supplemental fee of €100 per person may be applied on new departure dates.


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 €1280 per person
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