E-Bike Tour from Florence to Siena (5 days / 4 nights)

Florence – San Gimignano – Monteriggioni – Chianti – Siena

Long weekend 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.

We work in collaboration with Ride Tuscany of Anima Toscana for organization and technical support.


Day 1 – Welcome to Tuscany

Individual arrival and accommodation in 3 stars hotel located very close the city center of Florence.

Day 2 – The road to San Gimignano (56 km – elevation gain: 1010 meters)

This 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.

Light lunch with Vernaccia wine tasting in a winery with a beautiful view on San Gimignano.

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

Day 3 – Monteriggioni and Chianti region (49 km – elevation gain: 800 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. On the way to Castellina in Chianti we’ll stop in a Chianti winery for a light lunch with wine tasting.

Castellina in Chianti, the most medieval of the Chianti towns.

Dinner and accommodation in 4 stars hotel of Radda in Chianti.

Day 4 – The Castle  of Brolio and Siena (52 km – elevation gain: 820 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.

Wine tasting and lunch in Castelnuovo Berardenga.

Final arrival in Piazza del Campo, last unforgettable highlights of the bike tour,

Dinner in typical restaurant of the city center and accommodation in 4 stars hotel in Siena.

Day 5 – Goodbye

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.


  • 5 days / 4 nights



  • Hard



  • All year long


PRICES LIST (per person)

  • 2    people: € 1.350,00
  • 4    people: € 1.010,00
  • 6    people: €    980,00
  • 8    people: €    920,00



  • 4 Nights with breakfast
  • 2 Dinners, drinks not included
  • Day 2: light lunch and vernaccia tasting
  • Day 3 and 4: Chianti wine tour and tasting with lunch
  • Van support along the route
  • Expert bike guide
  • Baggage transportation between the hotels
  • Pick-up of everything you bought during your daily stage: wine, gift etc.
  • Maps and information for your daily stage

  • Tourist city tax
  • Drinks
  • Medical baggage insurance

OPTIONAL SERVICE (prices on request)

  • Medical / baggage insurance
  • Private transfer day 1 and 5 from airport, train station or hotels
  • Bike rental (hybrid, road bike or electric bike)
  • Flights
  • Activities for non-cyclist (cooking classes, wine tours, truffle hunting, horseback riding, trekking…)
  • GPS rental
  • Day 4: Cooking class with dinner
  • Guided tours

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