When you join our San Gimignano to Siena Boutique Bike Tour, you’re not just booking a ride, you’re stepping into a story that began more than a decade ago.
Back on a golden sunshine, long day of end of July 2013, a curious traveler from North America asked a simple question:
“Is it possible to visit San Gimignano and Siena from Florence in a single day—on a bike—and keep it moderate?”
That spark of curiosity ignited our imagination. Elena and Piero, founders of Bike in Florence & Tuscany and licensed tour operators, saw the challenge as an opportunity. They wanted to craft a journey that blended iconic Tuscan landscapes, authentic culture, and a pace as smooth as a Chianti Classico wine.
Designing the Dream
Elena and Piero personally mapped every turn of the route, scouting quiet country roads that wind through sun-drenched vineyards and rolling olive groves. They balanced moderate climbs with breezy, panoramic downhill stretches, ensuring a ride that was accessible yet rewarding.
Visit San Gimignano early morning to experience its medieval magic before the crowds arrive. Quiet cobblestone streets, golden light on the iconic towers, and the aroma of fresh bread from local bakeries create an intimate, timeless atmosphere, perfect for photos and a peaceful start to your Tuscany countryside bike tour.
A brief stroll through Monteriggioni is like stepping into a living medieval postcard. This perfectly preserved walled village, with its ancient stone towers and quiet piazza, offers a peaceful glimpse of Tuscany’s past and makes a charming pause on your San Gimignano to Siena bike ride. Tucked away from the usual tourist trail, it’s a spot cherished by locals and known to only a fortunate few visitors.
Siena is a must during any Tuscan stay for its breathtaking Piazza del Campo, world-famous Palio horse race, and magnificent Gothic cathedral. Rich in art, history, and timeless charm, this medieval jewel offers an authentic taste of Tuscany’s culture, cuisine, and vibrant local life.
By November 2013, this carefully curated itinerary became the very first feature on the debut version of our website. What began as a custom request evolved into one of our signature small-group, fully guided cycling experiences.
Why It’s a True Boutique Bike Tour
Our guests, primarily discerning travelers from the USA, Canada, and Australia, seek more than just a ride. They want:
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Small Groups for an intimate, personal atmosphere
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Fully Guided Support from expert local tour leaders
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Premium E-Bikes for comfort and performance
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Authentic Encounters, from medieval towers to hidden trattorias
This isn’t mass tourism. It’s luxury cycling in Tuscany, where every detail is designed with care.
The Experience Today
Starting from Florence, Piero and Elena lead you through the heart of Chianti .
You’ll explore the medieval skyline of San Gimignano, pedal across golden vineyards, and arrive in the historic city of Siena, where art, history, and tradition welcome you.
It’s a journey that remains faithful to Elena and Piero’s original vision: a moderate, unforgettable Tuscan adventure for travelers who value quality and authenticity.
Ready to Ride?
If you’re dreaming of a San Gimignano to Siena bike tour from Florence that combines luxury, small-group intimacy, and fully guided service, our boutique bike tour is waiting for you.
👉 Book Your Adventure Today and become part of a story that began on a crisp November day in 2013.
ANDIAMO, LET’S RIDE! With Love, Elena & Piero