Why choose this Florence tour ?

Enjoy a full-day tour visiting Tuscan villages and exploring the Chianti wine region! The villages of San Gimignano and Monteriggioni, the Chianti area, and the medieval town of Siena are situated in the heart of Tuscany. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Start your amazing journey in the first stop of Siena, the world-famous city of Palio horse-race in Piazza del Campo.
Afterward, head to our beautiful winery nestled in the Chianti Area, with scenic views of the Tuscan countryside.
Third stop, continue with a visit to the marvelous Monteriggioni castle, a medieval fortress that is really well preserved. You may also recognize it from the Assassin’s Creed video game series.
Last but not least, explore San Gimignano, another magnificent example of a Medieval urban town where you will have free time to visit the village and its splendid squares and towers.
At the end of the day, take your ride back to Florence.



Make the most of your Florence adventure

What makes From Florence: San Gimignano, Siena and Chianti Wine Tour a unique experience ?

Have some free time in this stunning medieval village also declared world cultural heritage from UNESCO due to its beauty and for its tower houses. This was also known as the “Manhattan of the Middle Ages”. You will have free time to visit everything you want in San Gimignano, such as taste one of the best ice-cream in the world at Gelateria Dondoli.

This is one of the gate to enter the medieval hamlet

During your free time you can decide to visit the beautiful Duomo located in the main square of the village. This is an extraordinary example of a well-preserved Medieval urban town, with the original old walls. This is also the main reason why UNESCO included this town into the world heritage sites.

If you wish to climb one original tower house and go back to the Middle Ages then you should climb this tower. From the top the view is stunning. This wonderful landscape will seduce you with its unique skyline made of towers. Most of the tower in San Gimignano were built during the 14th century by families who wanted to demonstrate their growing power.

One of the main squares of the village, has this name cause there is a wheel in the middle of the square. Admire beautiful palaces that face the square. The old town center is full of alleys and beautiful squares, museums, palaces, churches, magnificent towers and craftsmen’s workshops.

The tour will continue with a visit to the marvelous Monteriggioni castle, a medieval fortress that is really well preserved. You may also recognize it from the Assassin’s Creed video game series.

Admire this ancient fortress located right outside the center of Siena

Spend your afternoon discovering the city of Siena and its stunning center. In the afternoon the tour continues with sightseeing in Siena. Here our official guides will lead our tour to the old city center. You will have the chance to admire the magnificent Siena Cathedral (called Duomo) and the Town Hall in the Piazza del Campo, the scenery of the world-famous Senese Palio horse race.

From here you’ll start your guided walking tour with a local guide. Discover the history and anecdotes of the city. The best way to do this is on foot, admiring the city’s transformations over the centuries and enjoying spectacular landscapes and curious details.

One ancient Palace located in the heart of Siena. There will be no shortage of references to the great noble families, such as the Piccolomini, Tolomei and Salimbeni, and their palaces, the great tradition of the Palio di Siena, and also the stories of pilgrimage and sanctity that distinguish the city.

One of the main roads of the historical center. Pass here with your guide

The shell-shaped famous city center – Piazza del Campo, as the locals call it is an important spot for all the civic and political life of Siena, as well as the location for celebrations. Piazza del Campo is also where the famous Palio di Siena takes place, twice a year. Ten horses, representing the main districts, race around the square for the famous Palio event .

An ancient fountain covered with white marble located in Piazza del Campo. The fountain is formed by wolves which represent the mother of Romulus and Remus, to celebrate the link to ancient Rome. The original sculpted panels are not on the square – they were removed for preservation purposes, but you can now see them at Santa Maria della Scala.

This was the government of the Republic of Siena and also nowadays represent one of the city hall of the city. Here you will find the Civic Museum of Siena which houses famous paintings and frescoes, including the “The Maestà”

Siena’s Cathdral is one of the finest Gothic-Romanesque churches in Italy, and its beauty it’s s breathtaking. From the outside you will see three portals with the central one dominated by a bronze sun and the facade is in black and white marble, which are also the colours of the city.

Tour Description & Additional Info:

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels
  • A moderate amount of walking is involved.
  • Operates in all weather conditions, please dress appropriately
  • Entrance to the Siena Cathedral is not included, clients can enter at their own expenses and depending on Cathedral opening times. Please note that will not available on Sundays or Bank Holidays and during special event opening times can change
  • Please note that Portuguese option requires a minimum of 4 pax. Otherwise, the tour will be guaranteed in English.


Options To Choose for Your Trip:

  • Tour
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    Basic Tour
  • Portuguese Tour
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From Florence: San Gimignano, Siena and Chianti Wine Tour Inclusions:

Included with Your Ticket

  • Free time in San Gimignano
  • Wine tasting in a typical winery
  • Free time in Monteriggioni
  • Free time in Siena
  • Expert tour leader

Not Included

  • Hotel pickup and drop-off

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Special Instructions:

    Meet our staff at Villa Costanza, Florence Coach Station.
    How to get to Villa Costanza from Florence:
    take the tram T1.3*, direction ‘Villa Costanza’. It will take around 20 minutes to reach the destination.
    Once arrived, look for our staff member(s) wearing either a green t-shirt or a white shirt with green foulard with myTour logo, in front of The Florence Gate Caffetteria.
    *Please note that the tram ticket costs 1.50€ and you can get one at the vending machine close to the tram stop.
    For urgent communication please contact +39 0577236330

    Please be advised..

  • This Tour is Provided by myTour in Italy.
  • Tour Timezone & Starts at Europe/Rome.
  • Mobile or paper ticket accepted.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • This Tour is Rated 4 Stars based on 766 valid reviews on VIATOR.
  • Minimum 1 Travelers is required to book.
  • Maximum 15 Travelers is accepted for booking.