2-Day Chianti and Tuscany Bike Tour

Make the best of your trip: slow down and ride from Florence to Siena trough backroads on this multi-day experience!

Quick Details

Join us on a Two-Day full immersion bike ride in Chianti and Tuscany!

If you want to have a very special experience and connect more with Tuscany’s nature and local life, and if you can allow yourself the extra time, this is the Tour we suggest to you!

At We Like Tuscany, since 1993 we believe that the best way of travelling Italy (and Tuscany) is to slow down from past-paced travelling and the main tourist attractions, allowing our guests to have an authentic experience.

While most people go from Florence to Siena using the highway, this 2-day bike tour will allow you to travel through backroads and cross through all of the Chianti Classico wine region and some of the best medieval towns in it.

If you want an easier ride while still enjoying the breeze and slow-paced experience, electric bikes are available on request!



  • Chevron down Day 1 - Start your first day with our famous Classico Bike Tour and then keep riding!
  • Day 1 – Get escorted from our meeting point in Florence to the Chianti area (just a 20 mins drive!)

    Warm up with our Classic Chianti Tour in the morning. After lunch, we break off from the rest of the group and head further south towards Siena. During our trip, we pass through classic Tuscan towns such as Greve and the hilltop town of Panzano.

    After a coffee and a visit to the famous butcher of Panzano, Dario Cecchini, we head down to Villa Rosa where we will be spending the night. An exquisite Italian multi-course dinner in the hotel is included in the price.


  • Chevron down Day 2 - Discover Radda in Chianti, Gaiole, Pianella and Siena
  • 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 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, 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.

  • Chevron down Extra and infos
    • 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