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Self-guided bike tour

from Florence to Siena
Book now

From Florence to Siena

During this 5 day tour you will discover the heart of Tuscany. While biking from one place to the next, your luggage is being transported.

Discover by bike all that Tuscany has to offer while you ride all the way from Florence to Siena, through the hills of Chianti Classico and visiting medieval hamlets, castles and Romanesque churches.
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Programme

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. For dinner you have the choice of several restaurants with delicious dishes of local cuisine.
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Bike Rental

This tour is organised in close cooperation with a local bike rental company. They have selected the best roads to discover Tuscany by bike, alternating the uncontaminated nature of backroads with beautiful medieval villages, food and wine, nice lodging to stay in and relax at the end of the day.

You can customize this tour with any type of bike that you like. Our partner has a wide range of top quality bikes: hybrid bikes, MTB, electric bikes, E-bikes, gravel bikes or road bikes.
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  • In short
  • Itinerary
<
>
Duration: 5 days/4 nights
Level: Active ride
Where: Florence - San Gimignano - Chianti - Siena
When: from March to November
Type of terrain: 100% paved (Gravel roads on request)
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, 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.
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Dates

From March to November

Price from € 750,- p.p.

For 5 days based on occupancy 2 persons per room

Including:
  • 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 our local supplier

Exclusive:
  • supplement single room
  • contribution to the STO Garant guarantee scheme € 15
  • Tourist city tax
  • Medical insurance

Optional services:
  • Medical insurance
  • Bike rental (Trekking, road bike, Gravel or e-bike)
  • Van support along the route
  • Expert bike guide
  • GPS rental
Book now
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This offer is covered by the STO Garant guarantee. You can find the conditions for this guarantee scheme on STO Garant’s website (www.sto-garant.nl/en/downloads).

Transport

You can come with your own car, by train or by plane. The nearest airports are Pisa and Florence.
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Afbeelding
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Plant trees for a green and healthy world
Plant trees for a green and healthy world
© 2025 Triptoscana
  • Home
  • Stay
    • Vakantiehuizen
    • B&B
    • Luxe Villa's
  • Arrangementen
    • Kookreizen >
      • Koken in Toscane
      • Kookreis op maat
    • Luxe arrangement in Villa Petriolo
    • Pakketreizen voor- en najaar >
      • Pakketreis Fietsen
      • Pakketreis Wine & Food
      • Pakketreis Kunst & Cultuur
      • Pakketreis Strand & SPA
    • 5 dagen Self-guided bike tour van Florence naar Siena
    • 7 dagen Bike Tour door Toscane - Self Guided
    • Olijfpluk arrangement
    • Thermen & spa
    • Schildervakantie Toscane
  • Experience
  • Auto huren
  • Treinen naar Florence
  • Blog
  • Contact
    • Onze service
    • Over ons
    • Recensies
    • Nieuwsbrief
  • Home
  • Stay
    • Holiday homes
    • B&B
    • Luxury Villas
  • Package deals
    • Cooking Tours >
      • Cooking in Tuscany
      • Tailor-made cooking tour
    • Luxury package at Villa Petriolo
    • Spring and Autumn Holidays >
      • Cycling Holiday
      • Wine & Food Holiday
      • Art & Culture Holiday
      • Beach & SPA Holiday
    • 5 Days Self-guided bike tour from Florence to Siena
    • 7 Days Tuscany Bike Tour - Self Guided
    • Picking olives package
    • Thermae & spa
    • Painting Holiday in Tuscany
  • Experience
  • Rent a car
  • Contact
    • Our services
    • About us
    • Reviews
    • Newsletter
  • Startseite
  • Ihr Aufenthalt
    • Ferienhäuser
    • B&B
    • Luxusvillen
  • Pauschalangebote
    • Kochreisen >
      • Kochen in der Toskana
      • Individuelle Kochtour
    • Luxuspaket in der Villa Petriolo
    • Frühling und Herbst in der Toskana >
      • Radurlaub in der Toskana
      • Wein & Speisen Urlaub
      • Kunst & Kultur Urlaub
      • Strand- und Wellnessurlaub
    • 5 Tage Selbstgeführte Radtour von Florenz nach Siena
    • 7 Tage Radtour durch die Toskana - Selbstgeführt
    • Olivenernte-Paket
    • Therme und Spa
    • Malkurs in der Toskana
  • Erlebnisse
  • Autovermietung
  • Kontakt
    • Unsere Dienstleistungen
    • Über uns
    • Bewertungen
    • Newsletter