Crossing Chianti to Siena


Your Florence to Siena one-day bike tour in Tuscany featuring
Chianti colors, Medieval Villages,
wine tour&tasting.

The Crossing Chianti to Siena starts with your morning pick-up at the designated meeting point.

Comfortably seated in our air conditioned van you will be heading out of the city towards the open spaces of the Chianti landscape wherein only minutes you are far away from the busy historic center.
Immersed in the colors, fragrances and natural beauty of Tuscany, your day of adventure begins.


  • Air-conditioned van transfer to the starting point from Florence or surrounding
  • Piero & Elena – Company Owners-  leading your tour
  • Full van support
  • Visit San Donato in Poggio, one of  Most Beautiful Medieval Villages of Italy
  • Stop in Castellina in Chiant, visit the town square and the XXV century arched passages
  • Leisurely panoramic biking portion among vineyards, hills & small towns –
    Estimated biking time: 1.5 to 2.5 hours on the base of to the distance you choose – see below ‘Skill Level”
  • Full wine tour & tasting at organic farm – Chianti Classico wine
  • VISIT SIENA: Free time for sightseeing & lunch on your own (payable locally)


€ 155 per person


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

One day tour from Florence to Siena

Your day schedule
Pick up: 8.45 a.m.
Drop off: 5.00 p.m.

Biking Experience
From easy to advanced

Distance traveled by Cycling
10 to 18 miles (approx 1,5 to 2,5 hours)

The package

  • Your pick-up and drop-off in Florence – designated meeting point
  • Piero-Elena leading your day.
  • Full guidance
  • Air-conditioned van support.
  • High-quality light-frame 27-speed fitness bicycle, protective helmet, water bottle.
  • Full Wine Tour&Tasting at local winery in Chianti Classico (tasting fee incl.)
  • Snacks & fruit for your bike 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.

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

Itinerary & Tour Descripion

After your pick-up in Florence or surrounding we whisk you off in the Chianti Classico Region, stopping first to visit the picture-perfect small town of San Donato in Poggio.
Enjoy wandering the pretty streets, get a cappuccino at the local coffee bar and take a few photos.

Then hop again into the support van and venture deeper into the Chianti Classico territory.

Our next stop is Castellina in Chianti. Explore the town square, the arched passages from the medieval times before being fitted for your bicycles and safety equipment.

The pedaling portion of your Florence to Siena day trip starts from here.

Let your biking adventure begin, ANDIAMOOO!

Breathtaking view of the hills covered in rows of vineyards, olive groves, cypress trees and when in season, poppies and wildflowers will mark your quiet and relaxed pace until the next destinations.
While coasting along a gentle, scenic road, enjoy the must-stop gorgeous viewpoint – punto panoramico – to take the first souvenir photos of your memorable journey.
Amazing Fonterutoli Castle, a small antique hamlet owned by the same noble family since 1435, stands in front of you.
Let your guide tell you all about the black rooster symbol of Chianti Classico Region since 1716.

Your ride continues passing vineyards and olive groves till we come to historical residence Lornano,a true piece of history as well as an Organic Winery.
Here we stop and follow our host for a full wine tour&tasting savoring their extra virgin olive oil and balsamic vinegar.

After this wonderfully satisfying tasting experience, we venture forth for the last leg of biking, admire and capture the essence of Tuscany, its traditions, history, and charm.

In order to avoid the busy city traffic, we stop for one last panoramic view of the Chianti scenery, load up the bikes and you, before heading to the medieval walls of Siena, UNESCO recognized World Heritage site.

With its narrow streets, steep alleys, a stunning Gothic cathedral, and a bounty of early Renaissance art, Siena is often described as Italy’s best-preserved medieval city. We drop you off to explore the city and provide you with a city map to discover on your own.
And we give you a few insider tips on places for a great lunch & a delicious Italian gelato! 

After such a full day of excitement and emotions, our van is ready to provide you with a relaxing afternoon drive back to Florence.

Avid and experienced bikers can opt to start the biking portion of the tour from our first stop. If you are looking for the challenge, we will introduce you to some of the more demanding Chianti hills.



  • Distance traveled: about 10 miles/ 17 Kms.
  • Starting point:  Castellina in Chianti.


  • Distance traveled: about 13 miles/ 21 Kms.
  • Starting point:  Castellina in Chianti.


  • Distance traveled: about 18 miles/ 29 Kms.
  • Starting point:  San Donato in Poggio.