Discover Florence’s quiet and breathtaking countryside hills nearby Chianti, explore a countryside farm and its marvelous gardens, and enjoy a glass of Chianti wine and Extra Virgin olive oil tasting paired with traditional Tuscan cold cuts.
2 Day Florence to Siena Chianti bike tour
Make the best of your trip and ride from Florence to Siena through backroads for a unique multi-day experience!
Since 1993 we promise:
No museums, no churches, no annoying crowds!
- Adult (Ages 19+)
Immerse in the most famous wine region of Italy and experience it like a local
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.
We will cross it on a bike all the way from the northside (San Casciano) so the Southside (Gaiole in Chianti), with many stops and stories to be discovered along the way.
While most people go from Florence to Siena using the highway, missing all the scenery and the rolling hills, this 2-day bike tour will allow you to travel through backroads and see some of the best medieval towns of the region.
So come and learn about wine and olive oil making (and taste them!), eat traditional food in local trattorias and farms, sleep in a countryside Villa with pool, and share the experience with one of our knowledgeable guides.
In We Like Tuscany fashion, this is is a small group tour, and we promise you no churches, no museums, no annoying crowds!
If you want an easier ride while still enjoying the breeze and slow-paced experience, electric bikes are available on request!
Morning bike ride – start with our Chianti Classico bike ride!
Our friendly staff will meet you at our meeting point in Florence and take you with a shuttle (about a 15-min ride) to the Chianti Classico area where our bike shed is (15 minutes drive)
Your guide will fit you with bikes, helmets and water. You will then have a brief training session for safety and introduction to the itinerary for the day.
You will start biking in a private countryside road, to get comfortable with our high quality 24-speed hybrid bikes.
The first part of the bike ride lasts about 1.5 hours, and you will see typical Tuscany villages and Chianti wine fields while enjoying panoramic stops to take some photos and learn about local life and nature from our knowledgeable guide.
We will then have a stop also in San Casciano, one of the main villages of the Chianti region, and see the ancient city walls.
After another bit of biking, we will reach the wine estate for a tour of the property and a full Tuscan lunch!
Lunch and tasting – visit an exclusive Chianti Classico Villa and winery with underground cellar
The property you will visit has been owned by an ancient noble family of Florence for centuries, and it’s still run by them.
The ancient cellars are below the beautiful Villa and the Italian style gardens that we will visit.We will also have a peek at the “Orciaia“, a room filled with giant terracotta pots where wine and oil used to be stored since Roman times, and the “Frantoio“, the facility where the olives are pressed to produce the world-renowned Tuscan Extra Virgin Olive Oil.
We are then ready for a full Tuscan lunch and tastings at the Osteria of the Villa.
Lunch includes an appetizer, first course, dessert and coffee!
We will also taste 3 different wines and 2 types of olive oil, all produced on the premises.
Afternoon Bike Ride – on the way to Panzano in Chianti
After lunch, we will start biking again towards the medieval town of Mercatale and Greve, with a little stop for another coffee in the beautiful piazza (if you fell super Italian!).
The last biking section will be the most challenging, as we will ride up toward the hilltop town of Panzano in Chianti, to visit our friend and world-renowned butcher, Dario Cecchini. You might have seen him on the Netflix show “The Chef’s Table”. Now you will see him live!
Around 4.30pm we will reach the beautiful Villa where you will finally relax in your private room and have access to the pool if the weather allows.
A full Tuscan dinner is included as well!
Day 2 – After breakfast at the hotel, we start out descending downhill for several kilometers, leading us to the town of Radda in Chianti for our first climb. After a stroll through the famous town, another downhill takes us to lunch in the town of Gaiole, home of the world-famous vintage bike race called L’Eroica.
While sitting in the main square of Gaiole, we introduce you to our longtime friend and local restaurant owner, Fernanda, who will serve us a delicious Tuscan lunch.
After coffee, we ride back on the bikes for a nice long meandering, semi-downhill, flat stretch of road before we come to the town of Pianella.
After Pianella, we can stop here or proceed uphill to Siena (in our van or still pedaling), where we will say goodbye and our amazing experience together will officially end.
- Upgrade to an electric bike for an extra €100 per person! (request in advance)
- The Tour ends at Siena train station, you can then decide if going back to Florence or spend a night or more in Siena to visit (it is worth it!)
- Luggage transportation is included for both days