Cycle Florence to Siena

Cycle Florence to Siena

Trip Highlights

  • Cycling through the vineyards of Greve and Radda in Chianti
  • Visiting wineries on route
  • Discovering the impressive medieval cities of Florence and Siena
  • Enjoying the friendly hospitality and sampling the local delicacies of the region

Trip Summary

If you're short on time and want to pack in as much as possible during your time in Tuscany then spoil yourself with this self guided cycling trip from the Renaissance capital of Florence to the medieval masterpiece that is Siena. Florence needs little introduction and is a must visit city for anyone coming to the region. Arrive early to take in the magnificent squares, the Duomo, Ponto Vecchio, museums housing famous masterpieces, or just enjoy a walk along the Arno River. Your first stop will be at Greve, the capital of the Chianti wine-producing region, where you can taste over 50 different Chianti wines. It's then onto Siena via the picturesque town of Radda. Siena is one of the jewels of Italy and you'll soon agree once you visit the Cathedral, the Piazza del Campo and wander its maze of narrow streets and steep alleys.


This trip involves 2 days cycling with daily distances between 32 to 53km/20 to 33mi. The cycle route is mainly along well-asphalted country and secondary roads. As you approach larger towns you will cycle on roads with more traffic. The accent is on keeping a relaxed pace to take in all of the attractions, with time to stop and take photos. You will need a good level of fitness to participate fully in this adventure. *For safety reasons we insist that helmets are worn while cycling.


Today you will make your own way to the first hotel in Florence. Once you have checked in you are at leisure to explore this beautiful city. There is much to see and do in Florence including the Duomo, the Piazzale Michelangelo, the statue of David, and the San Lorenzo Market.

Meals:  Nil

After breakfast, you'll start cycling towards Greve in Chianti, a rustic market village and the capital of the Chianti wine-producing region. Along the way you can stop at Impruneta, which is a great place for a coffee break on the main square. When you arrive in Greve you can head over to Le Cantine di Greve where you can taste over 50 different Chianti wines. Overnight Greve. Cycling: +615m/2017ft - 467m1531ft, 3-4hrs

Meals:  B

This morning you start your cycle to the marvelous city of Siena, which is famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Along the way you can stop for a visit of the picturesque town of Radda in Chianti then arrive in Siena. Do not miss a visit to the Cathedral, an architectural treasure, and the numerous imposing medieval palaces. History comes alive as you meander through the narrow streets of this fantastically preserved jewel of Italy. Overnight in Siena. Cycling: +1000m/3280ft - 902m/2960ft, approx 5-6hrs

Meals:  B

The trip concludes in Siena after breakfast. We can assist with booking additional nights accommodation on request - please ask your consultant.

Meals:  B

What's Included

  • 3 breakfasts
  • 3 nights in 3 star hotels on a twin share basis with ensuite facilities (hotel taxes extra)
  • 21 speed rental bike with panniers, map holder / handlebar bag, repair kit, helmet and lock. A bike computer (one per room booked) is also included. Electric bikes available - supplement applies
  • Information pack including smartphone app with maps plus a route book per room booked
  • Luggage transfer - 1 piece of of luggage per person, max 20kg
  • Emergency hotline

What's Not Included

  • Travel to Florence and from Siena
  • Lunch, drinks and dinner daily
  • Entrance fees to museums, parks and archaeological sites
  • Items of a personal nature
  • Tour guide – this is a self guided trip
  • Travel insurance - mandatory
  • Hotel taxes (allow approx €10)

Upcoming Travel Dates


Be prepared for the hills! The Via Francigena passes through some wonderful country, and the small medieval villages are an absolute delight.

J. Kohlmoos, OR, USA, 19 Oct 2019


Duration:4 Days
Starting Point:Florence
Finishing Point:Siena
Grade:moderate  Click for more information
Trip Code:FLS
Prices From:GBP£680 Per Person
Single Supplement:GBP£100  Click for more information
Single Traveller Surcharge:GBP£280  Click for more information
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.