San Gimignano
to Siena

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

If you have little time in Florence and still want to see the beauty of Tuscany, emerging yourself in the gorgeous Tuscan landscape & culture, our exclusive San Gimignano to Siena bike tour is the perfect single day trip for you!

The San Gimignano to Siena Bike Tour is going to transport you back in time with three special stops from Tuscany’s medieval past:
San Gimignano, Monteriggioni and Siena!

Thanks to the beauty of the area and our tailor-made itinerary, safe and fun for everyone, the San Gimignano to Siena is not only our best-seller tour but also the perfect Family Friendly biking adventure in Tuscany.
It will be a thrilling excursion that combines cycling, history and sightseeing. Head into the marvelous landscape of Chianti to discovery Tuscany the way it was meant to be seen, slow & easy!

San Gimignano to Siena


  • Air-conditioned van transfer from Florence / Chianti area to the starting point
  • Piero & Elena – Company Owners- leading your tour
  • Fully guided and van supported Tuscany bike tour
  • Visit San Gimignano, the Tower Town UNESCO World Heritage Site with free time to walk around the city walls.
  • Leisurely panoramic biking portion among vineyards and small towns thru quiet, no traffic country roads of the Via Francigena –
    Estimated biking time: 1.5 to 2.0 hours on the base of to the distance you choose – see below ‘Skill Levels”
  • Brief stop in Monteriggioni, the Walled Castle : visit the town square of this awesome Medieval hamlet off-the-beaten path.
  • VISIT SIENA: Free time for sightseeing & lunch on your own (payable locally)
San Gimignano to Siena


€ 165 per person


Small group shared tour, from 2 to 8 people.
(larger groups may be accommodated by request)

One day bike tour in Tuscany

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

The package

  • Your pick-up and drop-off in Florence – designated meeting point
  • Air-conditioned van transfer to the starting point
  • Piero-Elena, Company Owners, leading your day.
  • Full guidance and air-conditioned van support.
  • High quality light-frame 27-speed fitness bicycle, helmet, water bottle.
  • Snacks&treats for your ride.
  • 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.
  • Non cycling tour-mates are welcome to join the party! Please contact us to learn more.
  • Min.Age for cycling : 12 y.o. 

Are you traveling with younger children yet fit, smart who love biking ? Let us know so that we can size your Family adventure on your need!

Itinerary & Tour Description

After you visit to San Gimignano we will move by van to the starging point of your bike ride.
The pedaling starts easy, alternating flat & gentle downhill stretches 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!

San Gimignano to Siena

After this second fascinating Medieval break we pack the bikes and drive straight to Siena.
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. 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.




  • 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.