Highlights:

• Ride from Florence to Siena along the most scenic stretches of the ancient Via Francigena
• Visit family-run farms and wineries, tasting Chianti, Vernaccia, olive oil, and local specialities
• Stay in charming countryside villas, with pool and panoramic views
• Explore iconic medieval towns like San Casciano, Greve, San Gimignano, Monteriggioni, and Radda
• Enjoy quiet backroads and UNESCO landscapes, with luggage transfer and an expert local guide included

Cycle from Florence to Siena on the Ancient Via Francigena – A 3-Day E-Bike Journey Through Chianti & Tuscany

Immerse yourself in the heart of Tuscany on this unforgettable 3-day E-bike adventure, following our signature route along Chianti Classico and the legendary Via Francigena.
This itinerary- crafted after 30+ years of guiding bike tours in Tuscany – blends countryside escapes, medieval towns, family-run farms, and delicious food and wine experiences.

From Florence to Siena, you’ll ride through landscapes most visitors never see: quiet backroads, olive groves, vineyards, hilltop hamlets, and UNESCO-listed towns, all at a relaxed pace supported by your local expert guide.

Day 1 — From Florence to Panzano in Chianti

(Approx. 40 km / 25 miles)

Meet your guide at our Florence office in the quiet Oltrarno district. After dropping off your luggage (we’ll transfer it for you), you’ll be fitted with your E-bike and gear before setting off through the panoramic Florentine hills.

Very quickly, Florence fades behind you as you ride past olive groves, vineyards, and charming backroads. A scenic stop at the ancient Certosa Monastery leads the way into the Chianti Classico wine region.

By midday, you’ll reach a family-run Chianti winery, meet the owners and enjoy a traditional home-cooked lunch paired with fresh extra-virgin olive oil and Chianti wines produced on-site.

In the afternoon, continue riding through San Casciano, Mercatale, and other quiet towns, before the final scenic push up to Panzano in Chianti, one of the area’s most iconic hilltop villages.
Your countryside villa awaits – with time to relax, enjoy the pool, or simply take in the sunset before dinner.

Day 2 — From Panzano to San Gimignano

(Approx. 45 km / 28 miles)

After breakfast, you’ll roll into classic Chianti landscapes of vineyards and cypress-lined backroads, connecting directly to the historic Via Francigena pilgrimage route.

Your morning ride leads you through peaceful hills all the way to San Gimignano, the “Manhattan of the Middle Ages,” famous for its medieval towers and UNESCO-listed beauty. You’ll have time to wander the town and soak up its unique atmosphere.

For lunch, visit another family-run farm, tour the property, and enjoy a tasting of olive oil, wine, and local specialties—including the famous Vernaccia di San Gimignano, produced only here.

You’ll spend the night in San Gimignano or nearby, with time to enjoy the village once most day-trippers have left.

Day 3 — From San Gimignano to Siena

(Approx. 51 km / 32 miles)

Today, you ride one of the most spectacular sections of the Via Francigena. The path winds up and down through postcard-perfect hills until you reach Colle Val d’Elsa – a perfect place for a coffee break.

A peaceful riverside segment follows, riding along the meditative Elsa River path, far from traffic and immersed in nature. The route continues to Pieve di Strove, with its Romanesque church, and then to the historic abbey of Abbadia a Isola, a pilgrimage stop for centuries. Lunch will be in Monteriggioni, a walled medieval gem beloved by locals.

The final stretch brings you through gentle dirt roads and past the hamlet of Cerbaia, before your triumphant arrival in Siena—one of Tuscany’s most splendid cities.

We typically end near San Domenico Church or at Siena Train Station, depending on your plans.

We highly recommend staying an extra night in Siena to explore this remarkable destination.

Note: Our van cannot enter Siena’s historic center, so please book accommodation close to the accessible drop-off area or plan for a quick taxi.