Tuscany: Cycle Siena & Chianti

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  • No booking fees
4.8 Based on 27 Reviews
  • duration 8 days
  • tour type Small group Request as private
  • age requirement 16-95 yrs
  • max group size 16
  • guiding method Fully guided
  • Tour Code BM-7759
  • Footprint Carbonneutral CO2 emissions resulting from all trips on Bookmundi will be offset via investments in carbon reduction projects.
  • Operated in English
  • Starts San Quirico d'Orcia, Italy
  • Ends Florence, Italy
HIGHLIGHTS Download trip notes
  • Explore the cultural cities of Siena and Florence
  • Enjoy Tuscan cuisine and wine
  • Visit some of the most beautiful hilltop towns in the region
  • Ride along the scenic country roads of classic Tuscany
Starting in San Quirico d'Orcia and ending in Florence, the trip "Tuscany: Cycle Siena & Chianti" is a guided bicycle trip that takes 8 days. You will travel through Pienza, San Gimignano, Chianti and 3 other destinations in Italy. "Tuscany: Cycle Siena & Chianti" is a small group trip which includes accommodation in hotels, transport, meals and others.

The Tuscan landscape is one of the most evocative and romantic in Europe, with cypress tree-lined roads, olive groves, vineyards, ancient hilltop towns and, of course, classic Renaissance cities. Our 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. We ride through historically diverse areas of Tuscany, such as the Chianti hills and beautiful countryside around Montepulciano. Riding north, we discover a wonderfully scenic region, home to some of Tuscany’s most beautiful towns and villages. We then enjoy the magnificent Piazza del Campo in Siena before biking past the towers of San Gimignano and on to our final destination in Florence. Following country roads wherever possible, we mix point-to-point and circular rides to make a perfect cycling tour of this region.

Did you know you can travel by train to this trip? Find out more here
  • Day 1: Start at your hotel in the Orcia Valley
  • Day 2: Circular ride through classic Tuscan countryside via the wine town of Montepulciano and thermal spa village of Bagno Vignoni
  • Day 3: Ride through vineyards and the walled town of Murlo to Siena
  • Day 4: Free day in Siena to explore or relax
  • Day 5: Ride via Gaiole and Radda to Castellina in Chianti
  • Day 6: Circular ride through the Chianti hills via towers of San Gimignano and Monteriggioni
  • Day 7: Cycle to Florence via Panzano and Greve in Chianti
  • Day 8: End Florence.
  • All accommodation
  • All breakfasts
  • All transport and listed activities
  • Group arrival and departure transfers available
  • Tour leader throughout
  • Local bike hire
  • Travel insurance
  • Single accommodation (available on request)
  • Visas or vaccinations
  • Local taxes
  • E-bike hire
4.8 - Excellent
Based on 27 reviews
  • Anonymous
  • On Oct 13 2019
5 - Excellent
Highly recommended
From the arrival on day one until the final departure this trip was so well run I felt totally taken care of from the cycling including the detailed briefings and advice, to the organisation of accommodation and the group meals. ... Read more
  • Anonymous
  • On Aug 29 2019
5 - Excellent
Fantastic cycling in stunning Tuscany
A well organised wonderful cycling tour with a perfect balance of cappuccino/gelato and lunch breaks, often in charming ancient hill towns where there was always time for a bit of exploring too. I've fallen in love with Tuscany... Read more
  • Anonymous
  • On Aug 25 2019
5 - Excellent
Great cycling in exquisite surroundings
Terrific trip. Just the right combination of decent cycling with culture, food and relaxation. A great opportunity to combine seeing Siena and Florence with some moderate exertion.
  • Anonymous
  • On Jul 01 2019
5 - Excellent
Scenic cycling tour
We very much enjoyed the trip. The countryside was beautiful and cycling was challenging enough but was still fun and rewarding. The food was excellent and the tour guide's choice of restaurants was very good.
REQUEST A PRIVATE, CUSTOMIZABLE DEPARTURE By design, this is a group tour. You can however request a private, customized version of this tour for yourself or your private group of people. Private departures are usually more expensive, but come with these benefits:
  • Personal Itinerary can be tweaked and customized.
  • Protected Travel within your own bubble.
  • Professional Access our Travel Specialists' insider knowledge.
  • Privacy Enjoy a tour focused solely on you or your travel group.
Request a private and/or personalized departure To design a private tour, we'll ask you some more information in the following steps.
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GOOD TO KNOW Download trip notes

No additional cancellation fees apply for this Tuscany: Cycle Siena & Chianti tour. You can cancel the tour up to 93 days prior departure and avoid paying the full amount, but your deposit paid is non-refundable. No refund applies for cancellations within 92 days of departure.


For any tour departures within 29 August 2023, full payment is required. For tours that depart later than 29 August 2023, a deposit of 25% is required to confirm this tour, and the remaining balance will be charged 92 days before trip departure.

Travel Insurance

Tuscany: Cycle Siena & Chianti tour requires that you have adequate and valid travel insurance covering medical and personal accidents, including repatriation costs and emergency evacuation. We recommend using World Nomads' travel insurance.


For this Tuscany: Cycle Siena & Chianti tour getting the required visa(s) is the responsibility for each individual traveller, as visa requirements vary depending on your nationality. We recommend to check with your local embassies representing the countries that you are traveling to, as part of this itinerary.

COVID-19 Safety Measures

This trip incorporates the following COVID-19 measures:

  • This tour has received the World Travel and Tourism Council’s ‘Safe Travels’ stamp, which provides travellers with assurance that COVID-19 health and hygiene protocols have been adhered to.
  • Group sizes are kept small to maintain a low risk ‘small group bubble’, with an average of 10 guests in each group.
  • Hygiene safety measures and distancing will be followed in transportation, accommodation and meal venues.
  • Several COVID-19 distancing measures have been adopted on this package tour to keep travellers safe.
  • All travellers will be required to be fully vaccinated no less than two weeks prior to travel.
QUESTIONS AND ANSWERS Find answers to the most frequently asked questions about this tour.
  • How many days are enough for Europe?

    You can spend a couple of months exploring Europe and still feel like you have not seen everything. Generally speaking, a two-week Europe trip should be just enough if you are looking to cover its major highlights. However, if you want a comprehensive travel experience within this duration, it is better that you focus on a region or a few countries rather than traveling all over the continent. 

    Choose a single country or schedule your trip around a handful of cities in different countries. While larger European cities may require three to four days to explore, you can get around smaller destinations in a day or two. Planning your trip around a particular region will cut down your travel time and save your time in transit.

  • What is the best month to visit Italy?

    The best time to visit Italy is between the months of April and June as well as from September to October. The weather on the Italian Peninsula during these months is ideal for going out on sightseeing tours, hiking, and exploring treasures stretching from Palermo to the lagoons of Venice. Traveling to Italy during July and August is avoided by many because of the summer heat and crowds, while the period between November to March sees the fewest visitors in big cities. However, these months coincide with the prime skiing season in the Alps, while southern parts of Italy, such as Sicily, remain relatively warm during this time of year. Find more information here.

  • Will I need a visa to travel to Italy?

    Citizens of the US, Canada, Australia, New Zealand, UK, and Japan can visit Italy (along with the free-movement zone of Schengen in the EU) for 90 days as tourists without requiring a visa.

  • Is an Italian holiday expensive? How do the ATMs work in Italy? What is the currency of Italy?

    While it is true that Italy is not an expensive destination, it is not exactly a budget destination either. Your vacation funds will go much further in Italy than they would in Scandinavia or the UK, with daily budgets of around USD150 per person sufficient for mid-range travelers who do not want to miss out on any of the country’s most important sights. Most banks have ATM machines (called bancomat) with English language options. All you need to do is look for the US or the UK flag. Plus, most machines accept both Visa and Mastercard. Please keep in mind that you will withdraw your cash in euros, with EUR1 slightly more than its USD equivalent.

  • Is English spoken in Italy? Should I learn communication phrases in Italy?

    It was not too long ago that finding anyone who spoke English in Italy was an ordeal. This is not the case anymore. Most people in the cities have some understanding of the language, although numbers decrease as you move further into the countryside. Therefore, it is better to know a few basic phrases in Italian (per favore means please and grazi means thank you) if you are heading for the country. This will not only make your stay in the country easier but also ensure that you show respect to the people and their culture.

If you have any question about this tour or need help with planning a trip, please do not hesitate to get in touch with us. We're ready to help.

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