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Cycling Florence, Siena & Chianti 8 Days

Siena is likely Italy’s loveliest medieval city with a historic center that has been declared by UNESCO a World Heritage Site. Enjoy this fascinating 8 day Cycling trip through some of Italy’s most beautiful spot. This tour is a Self-guided tour: Level of difficulty: 3.

Day 1 –

Siena: Individual arrival.

Day 2-

Siena–Radda in Chianti: (45 km, elevation up 900 m) – From Siena you start to head north towards the beautiful village of Radda in Chianti. The remains of its ancient walls show the historical significance that this town had in the competition between Florence and Siena.

Day 3 –

Radda in Chianti–Greve: (40 km, elevation up 500 m) – The route brings you to Greve over the rounded hills with beautiful views.

Day 4 –

Greve–Florence: (40 km, elevation up 600 m) – Florence, capital of the region of Tuscany, spreads on the banks of the Arno, between the Adriatic and the Tyrrhenian seas, almost in the middle of the Italian peninsula. Two of the many artists associated with Florence are Leonardo da Vinci and Michelangelo Buonarroti.

Day 5-

Florence: A full day to spend visiting Florence. The city is often considered the birthplace of the Italian Renaissance and was long ruled by the Medici family. Florence is also famous for its magnificent art and architecture.

Day 6-

Florence–Colle Val D’Elsa: (40 km by train + 25 km by bike, elevation up 480 m) – In the morning a short train transfer will bring you to Certaldo. From here you will then cycle further up to Colle Val D’Elsa.

Day 7 –

Colle Val D’Elsa–Siena: (40 km, elevation up 700 m) – From Colle Val d’Elsa you will cycle to the beautiful town of Siena, which is not only one of the most fascinating towns in Tuscany but it is also in a particularly beautiful position, with lovely surroundings.

Day 8 –

Siena: Departure. Possibility either to book extra nights.


  • Total Length: 195/255 km
  • Total vertical up: 3,180/3,970 m
  • Terrain: 95% asphalt, 5% unpaved
  • Train connection among the overnight stays: NO
  • Possibility to shorten the itinerary by taking the train: NO

Heavy, with sloping landscapes dotted with steeper inclines, but not overwhelmingly so. The daily distance is about 40 kilometers. Though the daily routes are not too long, they can be strenuous, so we do recommend being in reasonably good physical condition for this tour

Dates & Prices:

  • Code: GRLFSC15
  • Dates: Apr 2015 to Oct 2015
  • From: $1095.00 Cad p.p. based on double
  • Season 1: Apr 11 – May 1, Sept 26 – Oct 10: $1095.00 Cad p.p.
  • Season 2: May 2 – Sept 25: $1185.00 Cad p.p.
  • Special departure date requests requires a min. of 5 participants
  • Duration: 8 days

Services Included:

  • 7-nts accommodations in a charming 3***star hotel or a cozy B&B
  • Breakfast buffet
  • Free fenced parking place
  • Luggage transportation
  • Route descriptions & maps
  • 7-days hotline service

Not included:

  • Bike and Helmut – Bike Rental: $125.00
  • Extra Night: $70.00
  • Local taxes (approx 10-15 €)
  • Train transfer: Florence–Certaldo (approx. 50 min., 7 € per person + bike)
  • Any item not mentioned in “Included”

We’re eager to hear from you!
Contact our Professional & Expert Team to assist you:
TOLL FREE: 1.866.370.2277 or TEL: 250.764.3039
EMAIL: sales@vacanzadestinations.com

Price per person in CAD Dollars. Price indicative of Euro Exchange, CAD price subject to change.
Minimum 2 passengers. Rates & hotel availability subject to change.
High season surcharges may apply.

To book this tour, or speak with one of our representatives call Toll Free: 1.866.370.2277 OR click to email.