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5 Day Florence to Siena Self Guided Bike Tour in Tuscany, Italy
This listing has no upcoming availability. Check out these similar experiences

This listing has no upcoming availability. Check out these similar experiences

Exhilarating Bike Tour in Italy

Join this cycling holiday 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 such 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.

Key information

  • Trip type: Self-guided
  • Lodging: Point to point
  • Terrain: Hilly
  • Difficulty level: Moderate (cyclist needs to have a good level of fitness, terrain is mostly hilly or unpaved but they will ride on flat terrain sometime, 31-45 miles per day)
  • Total distance: 98 miles / 157 kilometers
  • Vacation type: Leisure cycling, road cycling
  • Type of bike: Hybrid and road bike
  • E-bike: Available to rent (40 EUR per day)


  • 3 days of cycling
  • Self-guided rides from Florence to Siena
  • Cycling through San Gimignano and Monteriggioni
  • Discover Montespertoli, Certaldo, Castellina in Chianti, and Piazza del Campo
  • 1 intervention of technical assistance along the route
  • Baggage transportation between the hotels
  • 4 breakfasts and 2 dinners
  • 4 nights' accommodation


3 days with instruction
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You will spend the first and second night in a three-star hotel. For the third and fourth night, you will stay in a four-star hotel.


Day 1: Benvenuti in Toscana

Individual arrival and accommodation in a three-star hotel located very close to the city center of Florence.

  • Hotel: 3-star
  • Included meals: Breakfast

Day 2: The road to San Gimignano, 35 miles / 56 kilometers

This stage starts with a very easy uphill to Piazzale Michelangelo, one of the most scenic panoramic spots over the city center of Florence. On the road, you will pass Montespertoli, a cute hilltop town surrounded by the beautiful view of the Chianti vineyards. You will also pass Certaldo, a 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 center, a UNESCO World Heritage Site. Dinner will be on your own and the accommodation will be in a three-star hotel in the city center.

  • Elevation gain: 1010 meters
  • Hotel: 3-star
  • Included meals: Breakfast
  • Optional activities: Light lunch with Vernaccia wine tasting

Day 3: Monteriggioni and Chianti region, 30 miles / 49 kilometers

The first landmark you will pass is Abbadia Isola, a beautiful abbey along the Via Francigena. After that, you will ride past Monteriggioni with its walls and the ring of towers that dominate the hill. You can take a break for a wine tasting after climbing up to the Chianti vineyards. Lastly, you will ride past Castellina in Chianti, the most medieval of the Chianti towns. Dinner and accommodation will be in a four-star hotel of Radda in Chianti.

  • Elevation gain: 800 meters
  • Hotel: 4-star
  • Included meals: Breakfast and dinner
  • Optional activities: Chianti wine tour and tasting

Day 4: The Castle of Brolio and Seina, 32 miles / 52 kilometers

You will ride to Radda in Chianti with its small street and a wonderful view of the vineyards. After that, you will pass Gaiole, the town where L’Eroica was born in 1997. You will also see The Castle of Brolio, the symbol of Chianti which offers good wines to taste. You will also ride past Villa a Sesta and San Gusmè, a cute town in Chianti and Castelnuovo Berardenga and its landscape museum. Finally, you will arrive at Piazza del Campo, the last unforgettable highlights of the bike tour. Dinner will be in a typical restaurant in the city center and the accommodation will be in a four-star hotel in Siena.

  • Elevation gain: 820 meters
  • Hotel: 4-star
  • Included meals: Breakfast and dinner
  • Optional activities: Chianti wine tour and tasting, and cooking class with dinner

Day 5: Arrivederci

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

Active rider

This tour is for a cyclist who rides a bike regularly, two times or more a week, comfortable with rides of two hours or more, who loves a physical challenge. You need to be able to ride in all terrain, paved and unpaved roads, with hills and some medium climb. The average daily rides are 50-100 kilometers per day, with around 1,000 meters of climbing. You’ll be riding during a part of the day, giving you the chance to visit the places along the path, to try some activities on your daily ride, alternating physical challenge to relax.


This bike tour will take place in Italy. It will start in Florence and end in Seina, through San Gimignano and Monteriggioni.


Four breakfasts and two dinners will be served for you.

The following meals are included:

  • Breakfast
  • Dinner

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

Things to do (optional)

  • Chianti wine tour and tasting
  • Cooking class with dinner
  • Cooking classes
  • Guided tours
  • Horseback riding
  • Light lunch and Vernaccia tasting
  • Trekking
  • Truffle hunting
  • Wine tours

What's included

  • 3 days of cycling
  • Maps and information for your daily stage
  • GPX tracks for GPS system assistance
  • 1 intervention of technical assistance along the route
  • Pick-up of everything you bought during your daily stage
  • Baggage transportation between the hotels
  • Anima Toscana phone assistance
  • 4 breakfasts and 2 dinners
  • 4 nights' accommodation

What's not included

  • Bike rental (hybrid, road bike, or electric bike)
  • Drinks
  • Expert bike guide
  • Extra intervention of technical assistance
  • Flights
  • GPS rental
  • Medical baggage insurance
  • Private transfer day 1 and 5 from the airport, train station, or hotels
  • Tourist city tax
  • Van support along the route

Cancellation Policy

  • A reservation requires a deposit of 25% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 30 days before arrival.
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