San Gimignano
to Siena

A fascinating journey from Florence to discovery three of the most beautiful Medieval towns of Tuscany:
San Gimignano, Monteriggioni, Siena


€ 160 per person

Tour Details

Small group bike tour, from 2 to 8 people

One day trip from Florence to San Gimignano and Siena

Your day schedule
Pick up: 8.30 a.m.
Drop off: 5.30 p.m.

Biking Experience
From easy to moderate

Distance traveled by Cycling
10 to 13 miles / 16 to 21 Kms

San Gimignano to Siena bike tour |

Our San Gimignano to Siena bike tour starts with your pick-up downtown Florence. With our air-conditioned shuttle, we head first to San Gimignano for an early morning visit (before the throngs of tourists arrive) to this UNESCO World Heritage Site with free time to walk around the city walls.

The pedaling starts downhill from here, where we will follow some of the most beautiful, and absolutely tranquil, back-roads. We start off using panoramic pieces of the famous “Via Francigena” which, in the Middle Ages, was used by pilgrims making their trek towards Rome for a blessing from the Pope.

You too get to be a “Pilgrim for a day“, following their footsteps, and in many cases gaze upon the same untouched landscape that they too saw as they moved further south. The typical white roads will guide us through vineyards, and sunflower fields with a few surprises along the way.

Biking at your own pace following gentle, soft rolling hills famous for their beauty, we will head to Monteriggioni. A stop to this village is mandatory! The castle, almost untouched by time, the church, the square walls, and the small specialty shops are just asking for photos!

After this second fascinating Medieval break we will head for  Siena on a gently curving road, through the typical Tuscan landscape with churches, castles, villages and beautiful fields.

We will deliver you to the ancient walls of Siena – another UNESCO World Heritage Site – in the early afternoon, with just the right amount of time for a light lunch. Spend your free time strolling the cobbled stone roads and amazing architecture in the city of the Palio and — why not? — have a delicious gelato downtown! Elena and Piero will provide you with a city map as well as the best recommendations for lunch: there are several delicious and affordable local options to choose from.

The San Gimignano to Siena bike tour concludes with us taking you back into Florence with our air-conditioned shuttle. You can just sit back and relax, while we navigate the road back to the city, where you will have time to tour the historic center or grab (another) gelato before dinner.

San Gimignano to Siena bike tour | Tuscany countryside | bikeinflorence.comHead into the marvelous landscape of Chianti on our amazing San Gimignano to Siena bike tour! Visit towns, vineyards. the Tuscany countryside the way it was meant to be seen, slow and easy, in just one-day trip from Florence!

Our exclusive San Gimignano to Siena Biking Tour is going to transport you back in time with three special stops from Tuscany’s medieval past:

San Gimignano, Monteriggioni and Siena!

It will be a thrilling excursion that combines cycling, history and sightseeing.

The San Gimignano to Siena Bike Tour features:

  • The Family-friendly biking adventure (min.age 12 years).
    Traveling with younger children yet fit, smart who love biking ? Let us know so that we can size your Family adventure on your need!
  • Free time in San Gimignano before the tourists arrive
  • Follow the via Francigena, low trafficked back-roads that the pilgrims in the year 900 trekked towards Rome
  • Walk through the fortress town of Monteriggioni
  • Free time in Siena to discovery the highlights of the Medieval city center
  • Estimated biking time: 1.5 to 2.5 hours

For those who are concerned about not being in shape, or who haven’t saddled up on two wheels for a while we have an alternative so that they don’t have to sit on the sidelines for this beautiful experience.

Ask us about our high-end Electric-bikes!

Non cycling tour-mates are also welcome in our small groups : contact us to learn more.

Elena & Piero say the San Gimignano to Siena bike tour is perfect for those who:

  • have little time in Tuscany and still want to see the beauty of the region
  • want to emerge themselves in the gorgeous Tuscan landscape & culture
  • travel as a Family with young kids.
  • This safe itinerary can be modify for those travelling with children under 12 y.o. Please let us know at the time of booking.



  • Distance traveled: about 10 miles/ 16 Kms.
  • Starting point:  from San Gimignano quick shuttle to the starting point of your tour/From Monteriggioni van transfer to Siena.



  • Distance traveled: about 13 miles/ 21 Kms.
  • Starting point:  from San Gimignano quick shuttle to the starting point of your tour.
  • Your pick-up and drop-off in Florence downtown –
  • Piero-Elena leading your day.
  • Full guidance and van support.
  • High-quality light-frame disk brakes 27-speed hybrid bike, helmet, water bottle.
  • E-bikes available on demand.
  • Snacks & treats for your ride.

We will be glad to pick you up even if you are staying outside Florence.
Please Contact Us for further details and personalized arrangements or Book Now your favorite.


Excellent tour of beautiful Tuscany!

My partner and I did the full day San Gimignano to Siena bike tour yesterday with Elena and we had a great day! Elena picked us up near to where we are staying and she was wonderfully friendly and chatty, pointing out interesting things to us as we drove to pick up the other couple doing the tour. We drove to San Gimignano and reached it before the crowds – it is a beautiful old town on top of a hill with amazing views of the surrounding area. Elena also recommended a delicious gelato place to us ? We then drove a little further and started the bike tour. The bikes were light weight and had lots of gear choices so riding them was very easy, there are also helmets provided. Elena drove ahead of us so we knew the route and we could catch up at our own pace. We were lucky to have beautiful sunshine and the scenery was very picturesque ? I don’t cycle a lot so I did struggle a bit with the hills – please be aware that as it is Tuscany there are some hills on the ride, but the hills are great as you get the best views on top and coming down. If the hills are too much you can always hop in the van with Elena for a while to rest ? We really enjoyed the stop at the wine tasting and the afternoon in Siena, Elena recommended a great place for lunch. We really enjoyed our day as we felt we saw some lovely little towns, amazing views and Tuscan countryside. Thank you!
Read more on TripAdvisor

Great tour and excellent way to see Tuscany

Our bike tour from San Gimignano to Siena, led by Elena and Simone was over way to quickly. 6 of us, ranging from 75 to 17 years of age, enjoyed a wonderful day with beautiful sights, great gelato and wine tasting. Our guides were very informative and very sensitive and accommodated everyone’s abilities. They were very friendly and professional too. We loved it all! Thank you for a fun-filled day! Linda

Even better the second time! – Bike Florence & Tuscany

Last year, I did the San Gimignano to Siena bike tour with the beautiful and amazing Elena. I had such a wonderful time that i immediately planned to do it again this year, on my birthday, as I couldn’t think of a better way to spend the day than on this wonderful trip! Well let me just say it was even better than I remembered! Not only is the scenery absolutely breathtaking, and the towns visited (San Gimignano, Monteriggioni and Siena) absolutely beautiful, but the hospitality, generosity and kindness of your hosts, Elena and Piero, are nothing short of unforgettable. I had not mentioned to Elena that it was my birthday, however she realised and so planned a few extra surprises for me – one, that the bike tour would be just myself and my sister (amazing considering it was June, high season!) and secondly, organising an amazing wine tasting for us in Monteriggioni (not normally an inclusion in this ride)!! This was such a wonderful and completely unexpected surprise to us, and I was so touched at her caring and generosity! I was completely blown away and really couldn’t thank her enough. Needless to say, I had an absolutely wonderful and unforgettable birthday thanks to Elena. The scenery on this ride is unbeatable, and you have ample time in each town to explore, buy souvenirs and have a coffee or gelato (or lunch) as you wish. Elena provides maps and great information on what to see and do in each place, and also plenty of water and snacks as you bike. This is just such a great way to see and experience Tuscany with locals who love Tuscany and love to bike!! The bikes themselves are fabulous – super light but sturdy – and with full van support there is no issue if you become tired. As should be obvious, I absolutely love this company and am planning on many more rides with them in the future. Thank you so much Elena and Piero for yet more amazing and unforgettable memories, and for the best birthday ever! Rosalinde

San Gimignano to Siena Exceeded our expectations!

It all started with a convenient pick up by our fabulous hosts Elena and Piero in Florence. From there we had a pleasant (and informative) drive to the historic town of San Gimignano — amazing! Our family of four then enjoyed a bike ride though the Tuscan countryside. We rode at our own pace, stopping for photographs and snacks. The riding was all done on quiet (almost no traffic), picturesque country roads. After completing our ride, we were treated to a wine and cheese tasting in the walled village of Monteriggioni. From there we were driven a short distance to Siena (in the super comfortable support van) where we were able to spend some time exploring this incredibly beautiful Tuscan city. Things to note: We completed our tour in December and despite it being winter, it was very pleasant. Thanks again to Elena and Piero for a memorable experience. Craig, Myf and Family