2-Day Florence to Siena E-Bike Adventure in Chianti

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
• 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 countryside villa in Panzano, where you can relax by the pool and take in the peaceful views.

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).

What’s Included

• E-bike, helmet, water bottle and luggage transfer
• Professional local tour leader throughout the experience
• Support van on day 2
• Overnight stay in a selected traditional countryside stay (double/twin room)
• Visit to a family-run farm with wine and olive oil tasting
• 2 Tuscan Lunches and a breakfast on day two

Dinner is not included and can be enjoyed directly at the hotel’s restaurant, where you’ll find traditional Tuscan dishes made with local ingredients. This allows you to choose freely from the menu according to your preferences.

What to Bring

• Sunglasses and sunscreen
• Comfortable sports clothing suitable for cycling
• Personal essentials for the overnight stay
• Valid ID

Before You Go

• 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).
• The tour is designed to end in Siena. Transportation back to Florence is not included.
• Good riding ability required and good fitness level – the E-bikes are not mopeds and you need to be in good physical shape.