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Bicycle Tours — Italy

Classic Tuscany Self Guided Bike Tour

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.

For more information download the Tour Factsheet

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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: climb up Giotto's tower for a stunning view of the city and the Duomo; visit the Uffizi Gallery, or walk the Ponte Vecchio bridge for a striking view of the city. We'll fit bicycles and we suggest a number of restaurants 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"!

Includes 7 nights accommodation in 3-4 stars hotels; all breakfasts; bike fitting and tour briefing in English; roadbook and map; GPS with preloaded tracks; luggage transfers
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 Tour Factsheet
Terms Terms & Conditions
Dates Prices Single Supplement
Dates Suggested start day: Thursdays
It can begin all days .
City taxes not included.

Please note that a High-Season Supplement fee may apply for the months of May and September

GROUP DISCOUNTS 5% (on groups of 4 or more)

Electric bikes available at an extra price.


  • A supplemental fee of € 150 per person will be charged on all new September departures (this fee will not apply to customers joining an existing departure date – please confirm available dates by contacting us, or use the Request Space form below)

  • Premium bikes, as well as e-bikes or other upgrade options, are subject to availability in September – please inquire
  • Prices €1270 per person

    Bike rental rates

    Premium titanium-frame bike €220

    Ebike €340

    Group Discount
    A 5% group discount will apply to the standard tour price
    Single Supplement €290 (solo travelers pay €800)
    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