Short Break – Chianti Classico & San Gimignano

4-day cycling tour from Siena to Florence through the Chianti Classico

Starting from

€ 860

A short 4-day tour from Siena to Florence discovering the Chianti Classico region and the medieval “Manhattan” of San Gimignano. A brief journey that introduces you to the culture and landscapes of Tuscany.

The tour begins in Siena, the famous city of the Palio, where every street and corner reflects the atmosphere of its medieval horse race tradition. In three stages you will ride toward Florence, the capital of Tuscany, a city that has always had a fascinating cultural contrast with Siena.

Along the way you will cross the rolling hills of the Chianti Classico region, home of the famous Gallo Nero wines, where carefully restored villages, villas, castles and ancient parish churches create a truly unique landscape.

The spectacular skyline of San Gimignano alone is worth the journey. Wineries for tastings, traditional osterias where you can recover after a day on the bike, and olive groves offering shade for a relaxing break are just some of the highlights of this short Tuscan escape.

Short Break – Chianti Classico & San Gimignano

Individual self-guided bike tour available in three different options:

E-bike / Touring bike
Gravel bike
Road bike

The route tracks vary depending on the selected option.

On request, a professional cycling guide can accompany you during the tour.

Itinerary

Read the full itinerary

Day 1
Arrival in Siena, with time to explore the city and enjoy an aperitivo in the shadow of the Torre del Mangia. Bike fitting and bike handover.

Night 1
We usually book a three-star hotel just outside the city walls, from where you can easily reach and explore the historic center.

Day 2
Today you ride toward Radda in Chianti. The first section introduces you to the famous Strade Bianche (white gravel roads), before reaching one of the highlights of the area, the Castle of Brolio, home of the Baron Ricasoli. You will also pass through Gaiole in Chianti, the village where the famous vintage cycling event L’Eroica begins.

Night 2
Hotel in the center of the village, giving you the chance to choose among several restaurants for a special dinner accompanied by Chianti Classico wine.

Day 3
Leaving behind the distinctive landscapes of Chianti, the view opens across the Val d’Elsa valley. Soon the famous towers of San Gimignano will appear on the horizon. Along the way you will have several opportunities to visit ancient parish churches and charming villages, and perhaps stop for a tasting at one of the many local wineries.

Night 3
We select a hotel in the historic center of the town with beautiful views over the surrounding countryside.

Day 4
Today you pass through Certaldo, the hometown of the writer Boccaccio, before continuing toward Florence. Along the way you will see the dome of Colle di Val d’Elsa, which inspired the famous dome of Florence Cathedral, before arriving at the gates of the cradle of the Renaissance.

Trip details

3 nights in B&B accommodation in three-star hotels or similar.
Each day you will have the option of an easier or a more challenging route, allowing you to enjoy the tour at your own pace and according to your energy level.
You will always have plenty of time to stop along the way, relax in a local trattoria and taste the delicious specialties of Tuscan cuisine.
Easy navigation with our preloaded GPS tracks.
7-day telephone support.
Luggage transfer from hotel to hotel.
There are no fixed departure dates and all tours can be adapted to your needs.
Minimum of 2 participants required.
Extra nights can be arranged at any stage of the tour, as well as before or after the trip.