San Gimignano and Siena Tour

Discover two of the most beautiful towns in Tuscany with us.
Pick-up, drop-off, transportation with a Mercedes car or van included!
Kids pay half price!​


about 9 hours

Great photo stops

Pick up at your hotel

Private Transportation

Professional Guides

Activity level


Sights Included

Siena walking Tour
– Duomo
– Piazza del Campo
– City center highlights
San Gimignano walking tour
– Unforgettable landscapes
– Unique medieval skyline
– Iconic buildings

Tour Description

San Gimignano & Siena Tour: discover two breathtaking Tuscan towns with us!

If you’re traveling through Italy, you need to visit Tuscany. And, once in Tuscany, you should not miss San Gimignano and Siena.

Our San Gimignano & Siena Tour will offer you the chance to visit two iconic Tuscan towns in a very comfortable way, with a private driver and a professional guide just for you.

1. Siena

Your driver will pick you up at your hotel and take you to Siena, the first stop of your San Gimignano and Siena Tour.

Seat back and enjoy your drive through the lovely Tuscan countryside, rich with vineyards that produce some of the best wine in the world.

Once in Siena, you will meet your private guide and start a full tour of the city.

Siena is one of the most exciting towns in Italy. Despite its size, it boasts many major attractions, like the Duomo or Piazza del Campo, and its whole historical center is a UNESCO site.

- Piazza del Campo and the Palio

The Senesi (inhabitants of Siena) are very proud of their culture and their traditions, the most intense being the Palio. Have you ever heard of it?

Twice a year, on July 2nd and August 16th, the contrade (neighborhoods) challenge each other in a passionate horse race that takes place in the heart of the city: Piazza del Campo.

Your guide will show you this lovely piazza, and tell you about the rituals and the activities that make the Palio so unique.

Then, you will continue your exploration of the city, wandering through the picturesque small streets that lead to beautiful piazzas where many people sit to enjoy some food or a drink.

- The Duomo

Our Siena tour also includes the Duomo, one of the most important churches in Italy.

Your private guide will show you the details of this wonder of Gothic architecture, unveiling the secrets of its construction and the hidden meaning of its overwhelming decoration.

But, Siena is also famous for its food. Ask your guide for a restaurant recommendation, and enjoy your pici with wild bore ragù, a ribollita, or some panforte.

2. San Gimignano

After lunch, you will get back in the car and your driver will take you to San Gimignano.

It was once a rich and proudly independent town, constantly in competition with the other cities in the area.

When San Gimignano was at its peak, during the Middle Ages, several wealthy families ruled the town.

In order to show their power, the aristocrats built many tall watchtowers, which are still nowadays the most impressive architectural feature of the town and created its iconic skyline.

Your guide will lead you through the picturesque alleys of the city, that offer unforgettable views of the Tuscan countryside.

You will learn about the fierce competition between the aristocrats, the political plots of Medieval Tuscany, but also of its great wine and food traditions.

San Gimignano offers great photo opportunities, and its dramatic views will create life-lasting memories.

Don’t forget to sit in one of the gorgeous squares, and spoil yourself with a spritz or a glass of local wine. That would be the perfect ending to your San Gimignano and Siena Tour.

The order of the town visited might change. 


You MUST bring an ID, a passport or a driver’s license to enter the sights.

Our standard San Gimignano and Siena Tour starts from Florence, but we can also arrange the pick-up and the drop-off in another town (the price might change)

This is the price for groups from one to six people. If you have more people in your group, please let us know and we’ll create a customized price.​​

1250 € for 1 person
99 € per additional adult
49 € per additional kid under 18
What's included

in a Mercedes car or van

Pick-up and drop-off at your hotel

if within the pick-up area

Book now!

through the booking calendar

June 2024
Contact us if you want more info or to design a tailored tour!
Send us a message using the form below, contact us via whatsapp icon Whatsapp, or call us at +39 376 165 1457




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    Tour Itinerary

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    Above & Beyond
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    We were amazed by the service we received in Rome and even in Benevento. Giovanni went above and beyond to organize tours and transportation for our family of 15 traveling. Massimo was an incredible and knowledgeable tour guide in Rome. He made it fun for the kids and knew when to take a break. Provided water and an amazing lunch spot for us all. We still are talking about some of the stories he told us. Stefano met us at the train in Benevento and was only supposed to drive us through San Bartolomeo, my father's hometown. But he pulled up my father's and grandfather's genealogy and found some interesting facts that were amazing to find out. He printed and laminated it for us to take. It was an emotional day but such a wonderful part of the trip. The minibus was perfect for everyone to fit comfortably and head over to Almafi. Thank you Giovanni and your amazing staff for making this trip one of the most memorable trips ever!!!
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    Giovanni was so exceptional at his job that you left the trip feeling torn between wanting to tell the World and also keeping him a best kept secret. Everything that he had orchestrated happened, seamlessly for us as if he had choreographed the entire country of Italy to show up, act, behave on queue. I put together a lot of trips, all over the world, for a group of around 20 friends each adventure. As the chief coordinator, you are always a little concerned about third party tours and tour guides: will everyone show up, is this a scam, can they speak English? Giovanni had infinite patience answering my questions and provided so much detail about our adventure, that everyone knew what to expect ahead of time. He took into consideration everyone’s interest, abilities and aptitudes. We saw a side of Italy that felt intimate and entertaining. There are not enough stars in the galaxy to award him.
    Great Experience!
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    What a great experience for me and my family to have these private tours planned by Giovanni. We wanted a curated set of events during our time in Rome and Florence and Gio delivered such a wonderful set of activities to suit my husband and I and our two teenagers. Each of the four days was a memorable experience. Alex was so fantastic and I would recommend him highly- we had one our best meals with him just learning from him and having great conversation. Andres in Florence was a blast and incredibly connected to the history of the area, just a wealth of information so much so that we are definitely coming back to Florence to spend more time. Caterina walked us through the Roman ruins and the Colosseum which was awe inspiring. And, one of the best things we did which I highly recommend is a pasta making class with Romina. We learned to make two dishes with her and then ate the food we had prepared. Such a great way to spend our time connecting to Roma. Thank you Gio and to all our guides! We will cherish our memories made together.
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    Giovanni-thank you for a wonderful itinerary of guided visits to all the sights in Rome! We so appreciated the communication and detailed planning that ensured our visits to the Vatican/St. Peter's, Colosseum, Hadrian's Villa and Florence came off without a hitch.
    Your guides are so friendly and knowledgeable. They made the history accessible and enriching.
    You covered every detail, down to lunch reservations, business class train tickets and wonderful air-conditioned transportation with friendly drivers!
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    I highly recommend Italian ArtVentures. We decided to use a private tour company, rather than the cruise ship excursions, and we were not disappointed. Giovanni was excellent at planning. We booked a tour in Rome and Pompeii. Giovanni was able to customize a tour that was special to us, so we could visit the LDS temple. Maria was our guide at the Vatican. She was fun, smart, and thoughtful. She translated for us as needed and was able to answer all of our questions. One major bonus of having a tour guide is skipping the line for St. Peter's Basilica. Our driver was awesome, traveling quickly and safely. The van was new, clean, and comfortable. We asked for a restaurant recommendation, and Giovanni made us reservations for Amalfi. It was incredible. The next day, we went to Pompeii with Stefano. He was fantastic. He made sure we saw the highlights and we avoided the crowds because of his expertise in the area. Booking was simple, communication was excellent, the cost was well worth what you get. This company is very professional. Totally awesome experience!
    Perfect Tour
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    Truly outstanding experience visiting the Vatican with Maria! She was the perfect guide - knowledgable, smart, funny, passionate about the subject matter. She had a deep knowledge of the art, architecture, history, and the religious significance of the whole area, and gave us thoughtful, interesting commentary throughout our tour. Although she seemed to have a bottomless knowledge of everything, she also knew how to present the information in a way that was considered, insightful, and crucially, not too overwhelming for us. As we walked, she called attention to many things, some big, others details that could easily be missed. She was well prepared, but also brilliant at answering questions and flexible about following our interests. Several times she pointed out a small detail, then drew a connection back to it later in the tour. She knew the Vatican, Sistine Chapel, courtyard and Basilica like the back of her hand, steering us to less crowded routes and perfect viewing vantages. One of us is Catholic, and one of us loves art, and Maria brilliantly held both our interests throughout the tour. Highly Recommend!
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