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$4395
Classic Level 2.5
  • Sep 29, 2024 – Oct 06, 2024
    Departure confirmed to go!

  • May 04, 2025 – May 11, 2025
    Book Now and Save $200 per person

  • May 18, 2025 – May 25, 2025
    Departure confirmed to go! Book now and save $200 per person.    

  • Jun 08, 2025 – Jun 15, 2025
    Book now and save $200 per person.

  • Sep 07, 2025 – Sep 14, 2025
    Book now and save $200 per person.

  • Sep 21, 2025 – Sep 28, 2025
    Book now and save $200 per person.

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 04, 2025 – May 15, 2025
    Book Now and Save $200 per person

  • May 18, 2025 – May 29, 2025
    Departure confirmed to go! Book now and save $200 per person.    

  • Jun 08, 2025 – Jun 19, 2025
    Book now and save $200 per person.

  • Sep 07, 2025 – Sep 18, 2025
    Book now and save $200 per person.

  • Sep 21, 2025 – Oct 02, 2025
    Book now and save $200 per person.

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$3150
Gravel Explorer Level 3.5
  • Sep 08, 2024 – Sep 14, 2024
    Departure confirmed to go! 

  • Apr 28, 2025 – May 04, 2025
    Book now and save $200 per person.

  • Sep 07, 2025 – Sep 13, 2025
    Book now and save $200 per person.

  • Oct 05, 2025 – Oct 11, 2025
    Book now and save $200 per person.

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 $1895
Self-Guided Level 3.5
  • Oct 14, 2024 – Oct 22, 2024