2 Day Florence to Siena Chianti bike tour

Highlights:

• Ride through the Chianti Classico hills on a scenic 2-day E-bike adventure from Florence
• Visit two boutique wineries and taste authentic wines and extra-virgin olive oil right where they’re made
• Stay overnight in a countryside villa with pool and dinner included
• Explore medieval towns like San Casciano, Radda, and Gaiole in Chianti
• Arrive in Siena by E-bike, taking in breathtaking views and a true sense of accomplishment

Immerse in the famous rolling hills of Chianti Classico and ride from Florence to Siena

If you want to connect with Tuscany’s nature and local life, allow yourself the extra time to travel off the beaten path and let us take you to meet and discover the Chianti Classico wine region.

Starting from Florence, we will cross the wine region on an E-bike all the way from the northside (San Casciano) to the Southside (Gaiole in Chianti), with many stops and stories to be discovered along the way (and food and wine tastings of course!)

While most visitors go from Florence to Siena using the highway, missing all the incredible scenery and the local life, this 2-day bike tour will allow you to travel through backroads and see the best medieval towns of the region.

Day 1 — From Florence to Panzano in Chianti

Your journey begins in Florence’s Oltrarno district, where our team will welcome you, store your luggage safely, and get you fitted with your E-bike and helmet.
After a short briefing, you’ll leave the city behind and follow quiet countryside roads lined with olive trees and villas, passing the Certosa Monastery and the Bellosguardo hills.

Riding toward San Casciano, one of Chianti’s most charming villages, you’ll stop for a guided visit and tasting at a family-run Chianti Classico estate, where you’ll sample wines and olive oils paired with a traditional Tuscan lunch.

In the afternoon, the ride continues through Mercatale and Greve in Chianti, with a stop in the village square in Panzano in Chianti, home to Dario Cecchini’s world-famous butcher shop and restaurant, featured on Netflix’s The Chef’s Table — a true symbol of local tradition and passion.

By late afternoon, you’ll arrive at your villa accommodation in Panzano. Take time to unwind by the pool or enjoy the peaceful views before your well-deserved Tuscan dinner.

Day 2 — From Panzano to Siena

After breakfast, start the day with a scenic downhill ride toward Radda in Chianti, one of the most picturesque hilltop towns in the region. Enjoy a short stroll through its medieval streets before descending to Gaiole in Chianti, home of the vintage cycling race L’Eroica, where you’ll stop for a Tuscan lunch.

We ride back on the E-bikes for a nice long meandering, semi-downhill, flat stretch of road before we come to the town of Pianella to then reach Siena.

The tour normally ends at Siena train station, but if you are staying in Siena (we highly suggest so!!) we might be able to get closer to the center with your luggage (but we can’t drive inside town with our van, as it is a restricted traffic area).