2 Day Florence to Siena Chianti bike tour

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 a 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.

This will also be a great chance to learn about wine and olive oil making (and taste them!), eat traditional food in local trattorias and farms, sleep in a countryside Villa or farmhouse, and be guided by one of our fun and  knowledgeable tour leaders.

As there are quite a few hills on this tour, 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 so you can drop off your luggage, we’ll take care of the transfer!

Your expert guide will fit you with bikes, helmets, and water. You will then have a brief training session for safety and an introduction to the itinerary of the trip.

The first part of the bike ride lasts about 2 hours, and from Florence, we will quickly get into the Bellosguardo area, where you will see ancient roads and villas, and great panoramic views over Florence and the amazing Certosa of Florence monastery.

We will then reach  San Casciano area, one of the main villages of the Chianti region, and see the ancient city walls.

After another bit of biking, we will reach a family-run wine estate for a tour of the property and a traditional Tuscan lunch!

We will also taste 3 different Chianti 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 in Chianti, with a little stop for another coffee in the famous town square.

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 4.30 pm we will reach the beautiful Villa where you will finally relax in your private room and relax a bit before dinner.

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 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 can0t drive inside town with our van, as it is a restricted traffic area)