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Tuscany Bike Tours

The rolling verdant hills of Tuscany make for excellent cycling

Welcome to Tuscany, a region lauded for its breathtaking landscapes, world-renowned wines, and an unrivaled tapestry of Renaissance art and architecture. In the rolling hills of Tuscany, where vineyards meet the horizon and medieval towns cling to the landscape, a bicycle becomes your time machine, transporting you through centuries of history, art, and culinary delights.

Tuscany’s historical roots stretch back to the Etruscan civilization, which thrived in the region before the Roman Empire. The city of Florence, the region’s capital, became a major center of the Renaissance, a period that birthed profound intellectual and artistic movements. Florence was also the heart of the Italian Renaissance, home to geniuses like Leonardo da Vinci, Michelangelo, and Galileo Galilei, whose innovations in art and science shaped the world.

Unlike any other region in Italy, Tuscany boasts rolling hills dotted with ancient vineyards, olive groves, and cypress trees, all set against the backdrop of a sun-softened and vibrant palette that changes with the seasons. In the gentle warmth of spring and the golden light of fall, you can experience the region at its finest: fields springing to life in a burst of color, grape harvests in full swing, and a slower pace of life that allows you to savor every moment.

Browse Tuscany tours

Cycling from Venice to Florence in Italy

Bicycling Venice to Florence
Our most popular bicycle tour in Italy for beginning cyclists offers a taste of three of Italy’s most spectacular cities.
8 days
From USD$4650
Classic Level 2.5

  • May 18, 2025 – May 25, 2025
    Sold out – wait list available. 

  • Jun 08, 2025 – Jun 15, 2025
    Departure confirmed to go!

  • Sep 07, 2025 – Sep 14, 2025
    Sold out – wait list available.

  • Sep 21, 2025 – Sep 28, 2025
    Contact us for availability     

  • May 03, 2026 – May 10, 2026
    Book now and save $300 per person.

  • May 17, 2026 – May 24, 2026
    Book now and save $300 per person.

  • Jun 07, 2026 – Jun 14, 2026
    Book now and save $300 per person.

  • Aug 27, 2026 – Sep 03, 2026
    Book now and save $200 per person

  • Sep 10, 2026 – Sep 17, 2026
    Book now and save $200 per person

  • Sep 20, 2026 – Sep 27, 2026
    Book now and save $200 per person.

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Bike Across Italy - Guided Bike Tours in Tuscany

Bike Across Italy – Venice to Pisa
If you love Italy, then you’ll love our bicycle tour from Venice to Pisa. Our “original” bicycle trip across Italy, includes a stop at our European headquarters.
12 days
From USD$6050
Classic Level 2.0

  • May 18, 2025 – May 29, 2025
    Sold out – wait list available. 

  • Jun 08, 2025 – Jun 19, 2025
    Departure confirmed to go!

  • Sep 07, 2025 – Sep 18, 2025
    Sold out – wait list available.

  • Sep 21, 2025 – Oct 02, 2025
    Sold out – wait list available

  • May 03, 2026 – May 14, 2026
    Book now and save $300 per person.

  • May 17, 2026 – May 28, 2026
    Book now and save $300 per person.

  • Jun 07, 2026 – Jun 18, 2026
    Book now and save $300 per person.

  • Aug 27, 2026 – Sep 07, 2026
    Book now and save $200 per person

  • Sep 10, 2026 – Sep 21, 2026
    Book now and save $200 per person

  • Sep 20, 2026 – Oct 01, 2026
    Book now and save $200 per person.

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Self-guided: Southern Tuscany – Cycling Cortona to Siena
Come cycle through this beautiful corner of Tuscany, stopping in Cortona, Montepulciano, Pienza, Montalcino; crossing the postcard Val d’Orcia region; and ending in the one-of-a kind city of Siena. The perfect Italian cycling itinerary!
Tour departs any Monday between March 1 and October 31.
8 days
From USD$2075
Self-Guided Level 3.5

  • May 01, 2025 – Jun 15, 2025
    High season pricing

  • Jun 16, 2025 – Aug 31, 2025
     Low season pricing

  • Sep 01, 2025 – Oct 15, 2025
    High season pricing

  • Oct 16, 2025 – Oct 31, 2025
      Low season pricing 

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Biking along the Adriatic

Self-guided: Italy Coast to Coast – Ravenna to Pisa
An epic bike itinerary, crossing Italy from the Adriatic to the Tyrrhenian, through the Apennine mountains. Start in marvelous Ravenna and end in Lucca, savouring the famous sites and discovering the hidden gems along the way!
Tour departs any Tuesday between March 1 and October 31
9 days
From USD$2375
Self-Guided Level 1.0

  • May 01, 2025 – Jun 15, 2025
    High season pricing

  • Jun 16, 2025 – Aug 31, 2025
     Low season pricing

  • Sep 01, 2025 – Oct 15, 2025
    High season pricing

  • Oct 16, 2025 – Oct 31, 2025
      Low season pricing 

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Explore the Strade Bianche on a guided bicycle tour with ExperiencePlus

Gravel Explorer: White Roads of Tuscany
In 1997, 92 cyclists pedaled out of Gaiole in Chianti, to protest the paving of Tuscany’s white gravel roads, or strade bianche. Two decades later the excitement around riding gravel hasn’t subsided and we’re thrilled to have a beautiful gravel bike tour from Siena to Cortona to showcase some of these stunning roads.
7 days
From USD$3295
Gravel Explorer Level 3.5

  • Sep 07, 2025 – Sep 13, 2025
    Departure confirmed to go!   

  • Oct 05, 2025 – Oct 11, 2025

  • May 03, 2026 – May 09, 2026
    Book now and save $300 per person.

  • Sep 06, 2026 – Sep 12, 2026
    Book now and save $200 per person.

  • Oct 04, 2026 – Oct 10, 2026
    Book now and save $200 per person.

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