Enjoy the far reaching views on this tour
Bike through changing landscapes of rural beauty
Cycle through the heritage of Tuscany
Enjoy experiencing the local flavors and tastes of this lovely part of Italy
Enjoy the comraderie of traveling in a friendly pack
Explore the iconic honey-colored buildings and rolling countryside of Tuscany

Bike Tours Tuscany: Siena & Chianti

8 days
Site savings
$2,367 USD

Ride along the back roads of traditional Tuscany on a classic cycling adventure over 8 days. The Tuscan landscape is one of the most evocative and romantic in Europe with cypress trees lining the roads, olive groves, vineyards, ancient hill-top towns and, of course, classic Renaissance cities. This group cycling tour is carefully planned to take in the best of Tuscany without feeling rushed: part of the joy of the Italian lifestyle is sitting and watching the world go by with a glass of wine in your hand!

  • Category
    Cultural & Historical
  • Type
    Fully Guided
  • Duration
    8 days
  • Culture Level
  • Skill Level
    3 - Intermediate
  • Activity Level
    3 - Active
  • Elevation
    3 - Intermediate
  • Terrain
  • Distance
    186.4 miles
  • Avg. Daily Distance
    37.3 miles
operated by
Exodus Travels
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  • Where does the tour start and end?

    The tour starts in San Quirico D'Orcia and ends in Florence. Fly in/out of either Florence airport (FLR) or Pisa Airport (PSA).

  • How long is the tour? How many cycling days?

    The tour is 8 days long with 5 days cycling.

  • What's the tour like?

    This trip is classified Road/Activity Level: 3 (Moderate). There is full vehicle support on this tour and the terrain is 95% tarmac, 5% easy gravel roads. This region is famous for its rolling hills, so be prepared for some climbing in places. This trip will require a moderate to good level of fitness as the area and rides are on undulating roads varying from 2km (1.2mi) hills to 9km (5.5mi) hill stretches on some days. Days 3 and 6 fall into the upper category of moderate grade riding, including some steep sections up to 10-25%. There are no transfers to or from hotels on this trip: all the rides are designed to be door-to-door.  The tour operator aims to use quieter country roads where possible, but sometimes you will need to pass busy sections surrounding towns. The most scenic routes are on tarmac, with occasional stretches of dirt/gravel roads (locally known as 'white roads').

  • Is a bike available to hire?

    Yes, a Ridgeback Element hybrid bike is included in the tour. E-bikes can be hired but is subject to availability and price changes.

    Alternatively, you can bring your own bike (BYO) but this is on a request basis and additional charges may apply to cover the transportation of your bike during the tour.


    1. The equipment remains the property of the supplier and you may not sell, hire out or part possession with the equipment.

    2. You must not misuse the equipment and must return it in the same condition as when received (ordinary wear and tear excepted). The supplier is entitled to charge for any damage caused to the equipment during the period of hire.

    3. You must ensure that the equipment is adequately secured when not in use. In the event of the equipment being lost or stolen, you may be liable for the replacement value of the equipment

    4. You must not use the equipment whilst under the influence of drink or drugs and should immediately notify the Supplier in the event of breakdown or loss.

    Extra Bike Bits

    You may like to bring your own pedals and saddle (excluding the seat post) or gel saddle cover to fit to the hire bikes. The tour operator encourages this, if it is your preference. However, please note that you are responsible for your own equipment, and removing your saddle/pedals at the end of the trip. They cannot guarantee the return of any bike parts left behind.

  • Do I have the wear/bring a helmet?

    Wearing a helmet is mandatory for anyone taking part in this cycling holiday. Group members must bring their own helmets, as they are not available for hire.

    Cycling of all kinds has its dangers and accidents can happen from time to time. Please ensure that you are properly prepared for the riding you are going to undertake.

    Recommended Cycling Clothing

    Padded cycling shorts (with loose 'over-shorts' where recommended), breathable clothing, and a lightweight waterproof/windproof top. Shoes with relatively stiff soles are better for biking but are not essential unless you are cycling long distances. Most people want to carry certain items with them during the day while cycling, for this we recommend a large bum-bag or small close-fitting daysack.

  • Should I have travel insurance?

    Yes. It is a condition of joining this holiday that you must be fully insured against medical and personal accident risks (to include repatriation costs and air ambulance or helicopter rescue services where appropriate). On arrival in destination for your trip, you will be asked to present details to your leader or local representative of your policy.

  • Can I have private room? What is the single supplement cost?

    A single supplement is applicable if you are travelling alone or wish to have your own room. The price varies depending on the dates chosen with minimum price starting at AU$533.00.

  • Are E-Bikes available on this tour?

    Yes, E-Bikes are available but they are on request basis. Availability will have to be checked along with its price since it is subject to change.

    Message us for additional information

  • Please read here for the tour operator's message regarding Covid-19:

    Update on trips running on or before 30 September 2021:
    As of Tuesday 25 May, 2021

    We hope you and your family are staying healthy throughout these trying times.

    Ensuring customer safety and enjoyment has been our primary focus since our first overland journey rolled out of London in 1974 and this fact has never been more important than today.

    We have introduced enhanced safety protocols in response to COVID-19, which are also in line with the World Travel & Tourism Council’s (WTTC) Safe Travel protocols for tour operators. As such, we are constantly monitoring whether we can safely travel to a destination country, along with what your home country’s current border restrictions are.

    We look forward to exploring the world with you again soon.

    If your trip departs on or before 30 September 2021:
    Due to the current international travel bans in Australia & New Zealand, will be contacting our Australian & New Zealand travellers to discuss your next steps (if you have not been contacted already). You do not need to call us. Please be patient while our customer teams work through bookings in order of proximity to departure.

    If you have booked via a travel agent, please contact them to discuss your options.

    Thousands of our wonderful customers have already chosen to rebook their holiday for 2022. In doing so they have not only given themselves an incredible adventure to look forward to, but they have also given hope to our long-standing local partners who rely on tourism for their income.

    If your trip departs on or after 01 October 2021:

    The vast majority of tours are currently planned to run as scheduled, however, we will be in contact with you directly should there be any changes to your specific departure.
    We will continue to monitor local conditions and all relevant governmental advice and will review all trips, and update passengers a minimum of 30 days prior to departure.

    Book with Confidence

    What you need to know:

    • You will receive a guaranteed refund if we have to cancel your trip for any reason.
    • You will receive a refund if you can’t join your trip because you or a member of your party is diagnosed with COVID-19 or has received a request from the Government to self-isolate, and you are unable to claim for this via your travel insurance.
    • Up to 21 days before departure you can transfer to another trip free-of-charge (excluding international flights, and any non-refundable in-destination costs). Please note on our self-guided range of holidays you can make changes free-of-charge up to 31 days before travel. View full booking conditions for details.
    • Up to 42 days before departure you can cancel free-of-charge and we’ll refund the balance, and hold the deposit for you to use on any departure in the next 2 years (excluding international flights, and any non-refundable in-destination costs - view full booking conditions for details).
    • Excludes Polar Expeditions and Voyages
    • Valid for new bookings made on or after 30th June 2020

Overall Rating:
Amazing adventure!
Jennifer Ford
(Review obtained from Tour Operator)

This was my first cycling tour and tour with Exodus. I had an amazing experience! The trip was well planned and I feel like it had the perfect balance of cycling, exploring towns on foot and good food. The level of difficulty was more than I thought. I trained in advance, which served me well, but I recommend others do the same, especially if this is your first bike tour.
What was the most inspirational moment of your trip?
Getting to the top of each hill is so rewarding. You definitely earn the views!

Awesome trip!
Kelly Young
(Review obtained from Tour Operator)

Fantastic trip, with Fantastic people! This was my first Exodus cycle trip, and for a Level 3, not only myself, but many others in the group found it a very challenging trip. The roads in this part of Italy, is either "up" or "down"...so with the weather being over 30C each day, each day was a bit challenging. I would definitely rate this trip higher than "Moderate", but having said that I thoroughly enjoyed the beautiful scenery, Tuscan hills, the food & wine, and all that Tuscany offers! Can't wait to do my next Exodus Cycle tour!!
What was the most inspirational moment of your trip?
Our group was so much fun! We all shared similar ages and cycle abilities, some more than others, but getting together each evening for dinner was a highlight! Love to cycle with this group again!
What did you think of your group leader?
Both David & Rebecca (Becks) were awesome leaders! They kept the team together, and always booked some awesome local restaurant for all of us to dine together. They always prepared us for the next 10-15kms, so breaking up the day with stops and lunch breaks along the way, made it for great cycle days.
Do you have any advice for potential travellers?
This cycle trip is not for the "light hearted"! You are climbing many long hills, and cycling down many windy roads. I would say recommend doing long steep hill rides before you venture to Tuscany! Having said that, it is so beautiful and rewarding...so definitely go, but make sure you get those hill cycles in before you go on this trip!

Great trip, difficulty rating a bit misleading
Peter Howe
(Review obtained from Tour Operator)

Our second trip with Exodus. A really good group of cyclists to ride and socialize with. Leaders Becs and David did a great job supporting us and handling both the expected and the unexpected. The scenery was spectacular. Having been on another level 3 tour, I would suggest that this one was significantly more difficult. I think Exodus needs to make some changes in the difficulty ranking system. I would be skeptical about the ranking and would want to talk to someone who had been on the trip I was considering. That said, we would do it again!
What was the most inspirational moment of your trip?
Besides making it to the top of some longer hills, as well as one 25% grade, we had one cyclist crash and damage his shoulder and ribs. I was impressed with my fellow travellers who looked after him until the leaders arrived on scene. I was impressed with Becs and David for the way they looked after him, his partner and still managed to look after all of us. Most of all, I was impressed with the injured cyclist and his partner. He stayed with us, rode the van, came out to dinner and kept participating despite what must have been a lot of pain. She rode the rest of the trip with us. I thought they both showed determination and toughness and it was great having them on the trip
What did you think of your group leader?
David and Becs did a great job of handling our group and dealing with issues that arose. Lots of energy, a few necessary untruths (undulating), great support and good fun. As did our last trip leader, I think they went above and beyond in supporting our vacation.
Do you have any advice for potential travellers?
Be skeptical of the difficulty rankings and try to find someone you can talk to about the trip and the difficulty. This one, Exodus got wrong.
Is there anything else you would like to add?
The bikes were adequate for what we were doing. Given the heat we experienced and the fact that we saw the van often, but not always, I would really like to see a second water bottle cage on each bike. The cost is very little, but being able to have a second bottle with you is important anytime, but especially in temps over 30 degrees. On our last trip, each bike had a pannier for carrying small items. These bikes had nothing. I suggest a small handlebar bag to be able to carry, for instance, some sunscreen and a wallet, maybe a few other items. The van was gone one morning for repairs and we carried a knapsack which would not be my choice. We did get frequent meet ups with the van, but sometimes not when it was needed and wanted. All in all, we like this company and the tours we have been on and hope to go on more.