Florence to Siena Bike Tour: Discover Hidden Gems of Tuscany in One Day

If you’ve ever dreamed of exploring Tuscany like a true local, there’s no better way than on two wheels. Our one-day Florence to Siena bike tour offers high-end travelers a perfect blend of history, nature, and gastronomy—all guided by Elena & Piero, a native Tuscan whose memories shape every route.

Every morning, we set off from Florence with a small group of guests, pedaling gently through the rolling hills and scenic landscapes that make Tuscany legendary. From vineyards to medieval villages, this Tuscan countryside bike tour captures the essence of Italy in a single, unforgettable day.

Explore all our Tuscan countryside bike tours

Florence to Siena bike tour - stop for picture


Piero’s Secret to Finding Hidden Gems

Many guests ask Piero: “How do you always find these magical, lesser-known spots?”

“Choosing the places to share is simple for me,” Piero explains. “Every stop is tied to my own memories. Visiting these towns with you brings back the joy of my youth exploring Tuscany by bike.”

  • Monteriggioni: Discovered by chance in the 1980s, Piero remembers a sunny piazza, a classic panino, and a glass of Chianti—a moment that made him feel truly Tuscan

  • San Gimignano, Castellina in Chianti, San Donato in Poggio ad a few others were favorites from teenage motorbike adventures, now highlights of our Florence to Siena bike tours.

Each village and vineyard in this Chianti bike tour from Florence has a story, ensuring every moment feels personal and authentic.

Cyclists gather in front of an ancient stone church in a historic Tuscan village, a cultural stop on a Tuscany bike tour.


What to Expect on Your One-Day Tour

Our moderate-level cycling tours are designed for enthusiasts of all abilities. Expect:

  • Scenic rides through Chianti hills and the Tuscan countryside.

  • Stops at hidden medieval villages and local artisan shops.

  • Gourmet experiences, from wine tasting to traditional Tuscan lunch.

  • Small-group attention with Piero&Elena as your expert guides.

This is more than a bike tour—it’s a storytelling adventure, letting you experience Tuscany as Piero remembers it, with every twist and turn on the road bringing history and culture to life.

  • “See our Florence to Siena bike tour itinerary


Luxury, Comfort, and Authenticity

Our tours combine authentic Tuscan experiences with comfort suitable for discerning travelers:

  • Personalized service and small groups ensure an exclusive experience.

  • Professional support and route planning take the stress out of cycling.

  • Every stop is hand-picked for beauty, charm, and local flavor.

Whether you’re a wine lover, history enthusiast, or simply want a day of cycling in breathtaking landscapes, this one-day Tuscany bike tour will leave you with memories to cherish.


Book Your Adventure

Are you ready to explore the Tuscan countryside on a Florence to Siena bike tour? Join Piero and our small-group tour to discover hidden gems, taste local wines, and experience Tuscany in a single day.

Reserve your one-day Chianti bike tour from Florence today!