Tuscany: Cycle Siena & Chianti

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  • No booking fees
4.8 Based on 29 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
The tour "Tuscany: Cycle Siena & Chianti" starts from San Quirico d'Orcia and ends in Florence. It is a bicycle trip that takes 8 days taking you through San Gimignano, Siena, Pienza and 3 other destinations in Italy. "Tuscany: Cycle Siena & Chianti" is a guided small group tour that includes accommodation in hotels, 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.
  • 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 29 reviews
  • Philip Hartlaub
  • From USA
  • On Sep 29 2023
4 - Very Good
Very Good
Very Good
  • Stanley Becker
  • From USA
  • On Sep 25 2023
4 - Very Good
Very Good
Very Good
  • 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
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 21 July 2024, full payment is required. For tours that depart later than 21 July 2024, 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. World Nomads offers travel insurance for independent travelers and intrepid families.


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.
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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