Self-guided bike tour from Florence to Siena

Self-guided bike tour from Florence to Siena


  5 days/4 nights


From 660,00 €


  Active rider

3 days bike tour where you can ride all the way from Florence to Siena, through the hills of Chianti Classico and visiting medieval hamlets, castles and Romanesque churches.
During the bike tour you will discover the history of Tuscany and the strong fight between Florence and Siena, Guelfi and Ghibellini.

The itinerary will take you up and down on the typical tuscan hill, surrounded by olive trees and vineyards and you will visit beautiful hilltop towns as San Gimignano, Monteriggioni and Siena.
At the end of each stage you can relax and taste some Chianti or Vernaccia di San Gimignano wines.
DURATION: 5 days/4 nights
PRICE FROM: 660,00 €
WHERE: Florence - San Gimignano - Chianti - Siena
WHEN: from March to November



Day 1 - Benvenuti in Toscana

Individual arrival, dinner on your own and accommodation in 3 stars hotel located very close the city center of Florence.
Hotel 4 stars available on request with extra price.


Day 2 - Road to San Gimignano

60 km – Elevation gain: 1190 meters

Breakfast and briefing with the staff of Anima Toscana, you will receive the maps and all the informations to complete the tour from Florence to Siena.

The first stage starts with a very easy uphill to Piazzale Michelangelo, one of the most scenic panoramic spots over the city center of Florence.
Montespertoli, cute hilltop town surrounded by beautiful view on the Chianti vineyards.
Certaldo, beautiful medieval town where the famous Tuscan writer Boccaccio, author of the Decameron, was born.
Uphill along the Via Francigena to San Gimignano, the towers of the town can be seen for miles around and the historic town centre is a UNESCO World Heritage Site.

Dinner on your own and accommodation in 3 stars hotel of the town center.

Hotel 4 stars located outside the town center of San Gimignano available on request with extra price.


Day 3 - Monteriggioni and Chianti region

56 km – Elevation gain: 970 meters

Abbadia Isola, beautiful abbey along the Via Francigena.
Monteriggioni with its walls and the ring of towers that dominate the hill.
Climbing up surrounded by the Chianti vineyards, take a break for a wine tasting.
Castellina in Chianti, the most medieval of the Chianti towns.

Dinner on your own and accommodation in 4 stars hotel of Radda in Chianti.


Day 4 - Castello di Brolio and Siena

58 km – elevation gain: 870 meters

Radda in Chianti with its small street and a wonderful view on the vineyards.
Gaiole, town where L’Eroica was born in 1997.
The Castle of Brolio, symbol of Chianti and good wines to taste.
Villa a Sesta and San Gusmè, cute town in Chianti.
Castelnuovo Berardenga and its landscape museum.
Final arrival in Piazza del Campo, last unforgettable highlights of the bike tour.

Dinner on your own and accommodation in 3 stars hotel located very close the city center of Siena.
Hotel 4 stars available on request with extra price.


Day 5 - Arrivederci

Check-out and individual departure, optional transfer on request. Otherwise you can decide to add more days to your stay and visit this beautiful city.

  • 4 Nights stay with breakfast in double room
  • Baggage transportation between the hotels
  • Maps and information for your daily stage in PDF file
  • GPX tracks for GPS system
  • Phone assistance by Anima Toscana staff
  • Tourist city tax
  • Medical insurance
  • Medical insurance
  • Private transfer day 1 and 5 from airport, train station or hotels
  • Bike rental (Trekking, road bike, Gravel or e-bike)
  • Flights
  • Activities for non-cyclist (cooking classes, wine tours, truffle hunting, horseback riding, trekking…)
  • Van support along the route
  • Expert bike guide
  • Extra intervention of technical assistance
  • GPS rental
  • Day 2: light lunch and vernaccia tasting
  • Day 3: Chianti wine tour and tasting
  • Day 4: Chianti wine tour and tasting and Cooking class with dinner
  • Guided tours
From 660,00 €