Cycling in Tuscany region of Italy
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
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 04, 2025 – May 11, 2025
May 18, 2025 – May 25, 2025
Contact us for availability. .Jun 08, 2025 – Jun 15, 2025
.Sep 07, 2025 – Sep 14, 2025
.Sep 21, 2025 – Sep 28, 2025
Departure confirmed to go! .
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
May 18, 2025 – May 29, 2025
Contact us for availability. .Jun 08, 2025 – Jun 19, 2025
.Sep 07, 2025 – Sep 18, 2025
.Sep 21, 2025 – Oct 02, 2025
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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
Apr 28, 2025 – May 04, 2025
.Sep 07, 2025 – Sep 13, 2025
Departure confirmed to go! .Oct 05, 2025 – Oct 11, 2025
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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.
Tour departs any Monday between March 1 and October 31.
8 days
From
Self-Guided
Level 3.5
-
No dates currently scheduled.
Private departures available.