Florence to Siena and San Gimignano Tour, Glory of Medieval Age in Tuscany

Tuscany Tours

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Traveler reviews


If you are in Florence you can not miss a Tuscany tour and especially your private tour Siena, the city that for centuries has been the great rival of Florence in Tuscany and to tour San Gimignano the famous city of the stone towers immersed in the Tuscan Countryside.


If you choose to see the Medieval Tuscany with us, after meeting you in front of your residence, we will start the Siena and San Gimignano tour firstly going to the city of Siena with a short drive.
We can reach the heart of Siena with our luxury vehicle where your driver will escort you discovering the most striking monuments: the Siena Cathedral (your driver will help you finding the Siena Duomo Tickets office), the Campo square, the Palazzo Pubblico, and central lively Via dei Banchi (or the Bankers road).


Your driver will expertly introduce what to see in Siena and the most important highlights, the history and the most important tradition of Siena:


The Palio horse race, a touching medieval competition that take place every year July 2nd and August 16th in the central Campo Square in which the 17 districts of Siena called Contrade participate.

You will discover the traditional savory Tuscan Food and famous Tuscan Wines as "the good table", as they are one of the most significant attraction.


During your visit to Siena you'll have enough time for some shopping and for taking memorable photos.


We can also propose to reserve your Siena walking tour with our knoledgeble certified guide that will escort you and will explein with details the most important sights.


You can choose to have lunch in Siena in a typical Tuscany restaurant Trattoria (family restaurant) close or in the “Piazza del Campo” square.


Alternatevely you can venture a breef wine tour from Siena to the Chianti hills to have lunch at a wine estate and taste home made Tuscan food paired with local wines. This option will add some time to your tour.


After lunch we will drive you to marvellous stone tower town of San Gimignano where, in addition to visiting the city, perhaps climbing up the “Torre Grossa” (huge tower) from where you can admire one of the most beautiful Tuscany landscape or entering the Cathedral.


You can enjoy a magnificent San Gimignano gelato (ice cream) at the Gelateria Dondoli, a true artisan awarded as Gelato World Champion on various occasions and destination of a real pilgrimage.


Once the day tour is over we will take you home while admiring the Tuscan countryside and its charm that will be a memory for a lifetime.

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For more than three centuries from 1200 to 1500 Florence and Siena have been competing in wealth and power, in the number of architects called upon to build public palaces and the marvelous residences of the noble families and for the artists who have decorated the churches with travertine facades.

Siena owes its glorious past to a particularly favourable historical moment in which the production of the world's finest fabrics at that time and the  birth of a new generation of adventurous merchants, who have travelled throughout Europe, have been supported by the birth of the Modern Bank, with new kinds of loan and interests that have made this area the financial capital of Europe. In Siena you can admire the  headquarters Palace of the oldest bank still active in the world, the "Monte dei Paschi" founded in 1472.

Siena had an enlightened Pope, Pius II, to whom one of the chapels of the magnificent Cathedral of Siena is dedicated, a unique example of Medieval architecture built in marble from 1200 onwards.

The government of Siena in the Middle Ages was assured by a council composed by members of the noble Sienese families and representatives of the artisans' guilds.

The “Council of Nine” gathered in the famous Palazzo Pubblico that stands out in Piazza del Campo, an immense square in the shape of a Shell, paved with terracotta bricks, that has always been the social and economic center of the city and where from 1200 still, twice a year, the famous Medieval horse race called the Palio takes place.

In case you are interested in a more indepth visit of Siena and its local history or simply prefer to be accompanied in a walking tour, we suggest you to enquire for our certified guide.

Not far from Siena, among the Chianti hills cultivated with vines and olive groves, there is another medieval town that has preserved some of its high Stone Towers that controlled the Via Francigena (Frank route) on which the pilgrims and merchants of Europe walked to Siena and Rome.

San Gimignano, preserves still today the charm of a real medieval town where a white wine, famous since the Middle Ages, is produced using a local grape variety: “Vernaccia di San Gimignano DOCG”.

Excellent extra virgin olive oil, painted pottery, art galleries, leather goods,  are also important local produce. You will find them in the shops that you will discover strolling the enchanting stone paved backstreets of the old town, while admiring the architectural wonders, made by medieval masters, which in some cases resisted to wars and time for over 800 years.




  • Tour Available: All year round. Rain or shine
  • Duration: 8/9 hours
  • Traveling time: 3 hours
  • Tour Area: Siena and San Gimignano (and Chianti as option)– (see map)
  • Allergy Caring: We can cater to all sorts, please let us know ahead of time.
  • Wineries (as option): Well Rated
  • Wine Tasting (as option):
  • Reds: Chianti Classico – Sangiovese grape mainly
  • Whites: Vernaccia di San Gimignano DOCG



  • Luxury Air Conditioned vehicle
  • Fluent English speaking Driver,
  • Panoramic Drive through the hills of Chianti
  • Visit of the city of Siena and San Gimignano
  • Pick up and drop off in Florence or its immediate surroundings.
  • All local Taxes, gasoline, driver's meal


Please note that you can pick up at your place outside of Florence.

We are also available to personalize your itinerary,


2) visiting a winery for lunch.

Contact us and we'll send you a personalized program and quotation.


Tour Prices


Starting from  70 euro per person

Based on the number of partecipant

Private tours only



  • Lunch at the restaurant or as option at the Winery with typical Tuscan food paired with Chianti and/or Vernaccia
  • Admission fees where required
  • Walking guided tour of Siena with local certified guide (HIGHLY RECOMMENDED ON REQUEST)



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