Home > Day trip: San Gimignano, Siena and Chianti

Chianti and Tuscany: discover the landscapes, villages and wine of Tuscany

Enjoy a full-day tour of Tuscany wine regions. Come with us during a day trip and travel to the heart of the Tuscan countryside. We’ll take you to visit the town of San Gimignano, the Chianti wine region, the medieval town of Siena and the well-preserved Monteriggioni castle. Follow us on a journey through space and time!

Experience the unique cultural landscape of Tuscany and its beautiful medieval towns on a day trip

Siena, San Gimignano and Monteriggioni: the most beautiful cities in Tuscany in one trip

The tour will first stop in San Gimignano and continue with the Chianti area, known for the Chianti Classico Riserva and its symbol Gallo Nero, and the Medieval town of Siena, both situated in the heart of Tuscany. All these are compelling stops for those who want to see the true Tuscan landscape. You will learn about the region’s history and traditions from the 13th Century. You will taste excellent food and wines.

San Gimignano: the city of towers

The town of San Gimignano relies on the top of a low hill at the centre of Valdelsa. 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. At those times, after gaining the autonomy from Volterra, more than seventy towers have been built in San Gimignano town centre. This process was transforming a rural village into a prestigious town. 

Siena: medieval Gothic in one of the most beautiful cities in Italy

The historic centre of Siena has been a World Heritage Site since 1995. A horse race - the Palio di Siena - has been held twice a year on the central Palio di Siena square since the Middle Ages, with the 17 districts of the city competing against each other. Not only is the cathedral really worth seeing, the city also has several other sights to offer: the museum attached to the cathedral, the pilgrims' hospice Santa Maria della Scala, the town hall Palazzo Pubblico, the Pinacoteca, the oldest bank in the world Banca Monte dei Paschi di Siena and much more.

Monteriggioni: the castle on the hill

The small village is located on the Monte Ala mountain. The medieval town wall - around 2 metres wide and 570 metres long - with its 14 towers is almost completely preserved and surrounds the medieval town centre. The church of Santa Maria Assunta dates back to the 13th century. In the 18th century, a campanile (free-standing bell tower) was built alongside it.



  • Discover the most beautiful cities and towns in Tuscany: Siena, San Gimignano and Monteriggioni on a day trip 
  • Find out more about the Tuscany wine region and its famous Chianti wine 
  • Included: Vino Chianti and snacks
  • Travel by GT coach or air-conditioned minibus 
  • Expert multilingual escorts 
  • Wine tasting at a winery in the heart of Chianti  



1 April - 15 November
Tue-Thu-Fri-Sat: 8:45 AM 

16 November - 31 March
Thu-Sat: 8:45 AM

Duration: 11 hours



Please book this tour at least 10 hours in advance by email to booking@mytours.it, state that you are a Turbopass customer and communicate your ticket codes of your Florence City Pass 

Choose language: Italian, English, Spanish, Portugues


Information and restrictions

  • Free time in San Gimignano 
  • Free time in Siena 
  • Free time in Monteriggioni 
  • Please note that a moderate amount of walking is involved and this tour is not wheelchair accessible. 
  • The tour planning can be different, but you will always do all the tour stops. 
  • 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 be available on Sundays or Bank Holidays and during special events opening times can change 
  • The tour in Portuguese is only confirmed when there are 4 participants. 



Meeting point

Instructions to reach the meeting point: Meet our staff, who will be wearing green shirts, at Villa Costanza, Florence Coach Station.You can easily reach the meeting point by getting on T1 Leonardo tramway towards Villa Costanza (you have to get off at Villa Costanza stop which is also the end of the line). 

It will take almost 20 minutes from Florence main train station. 



Meeting Point at 08:45 

Florence Coach Station
Villa Costanza (Tram T1)

(Please come 15 min earlier!)

Google map icon

Click here
to see on google maps

Scroll to top

Florence City Pass

Free admission to Florence's museums, attractions, and tours. Discounts included.

citypass buy
Book now

incl. VAT and service fees, free shipping via e-mail