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Traveller Rating


  • self guided cycle
  • 3 nights hotels
  • 3 Breakfasts

4 Days£840GBP


Trip Code: FLS

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

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.



Starting Point:


Finishing Point:


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, there's a bike fitting at 9am before you 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



The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.


  • 3 breakfasts
  • 3 nights in 3 star hotels on a twin share basis with ensuite facilities (hotel taxes extra)
  • 21 speed rental bike with phone holder, pannier, lock, repair kit and helmet, 1 odometer per room (e-bikes available - supplement applies)
  • Digital information pack including smartphone app with maps and route information
  • Luggage transfer (max 1 piece, max weight 20kg and max size 60 x 50 x 40 cm per person). Supplement applies for excess
  • Emergency hotline

  • Travel to Florence and from Siena
  • Meals not listed as included, drinks
  • Entrance fees
  • Guide – this is a self guided cycling holiday
  • A supplement will apply if you are travelling solo or book a single room
  • Travel insurance
  • Excess luggage
  • Hotel taxes (allow approx €10)
  • Items of a personal nature

Bike information




This trip involves 2 days cycling with daily distances between 33 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.

Departure dates

Daily from 1 Apr to 31 Oct


Black out period: 26 - 30 Jun, Palio Horse Race, Siena

Priceper person from


Options & Supplements*
  • Discount for triple share rooms (pp)GBP£-72
  • Optional 2nd pannierGBP£10
  • e-bike supplementGBP£30
  • Single supplementGBP£120
  • Solo Traveller SupplementGBP£460
*Prices listed are per person

Trip reviews

Why travel with us

Personal Experience

We've been walking and cycling the planet for over four decades and are passionate about delivering exceptional service. Combined, we’ve travelled to virtually every corner of Europe, and are eager to share the many benefits of travelling on foot or by bike.

Great Value & Quality

Our well priced trips offer great value for money. Included in your package are comprehensive route notes, maps & guide books along with bag transfers and locally run accommodation. We take the stress out of organising your holiday.

Self-Guided Specialists

We have been operating active self guided holidays since 1973. We handle all the necessary logistics so that you can relax and explore your destination at your own pace. Many of our tours depart daily, giving you even greater flexibility.