Siena & San Gimignano Day Trip

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Discover Siena and San Gimignano on Your Private Tour

Siena is perhaps the most popular destination for a day trip while visiting Florence or Tuscany. Siena is the famous city of the Palio, the site of the Enoteca Italiana, Italy’s only national wine association. The city is also the location of Monte dei Paschi, the oldest bank in the world. Siena is a tourist dream for those who want to experience an old-world city while still having access to modern conveniences. Nearby San Gimignano is the only Italian towered hill town that has managed to be preserved its original medieval appearance intact. The town is close to Monteriggioni, an impressive 13th-century fortress, immortalized by Dante in the Divine Comedy.

The perfectly preserved gothic city center is perhaps the main reason that the city of Siena is so popular with tourists. The city center sits at the core of the town which is laid out across three hills. The Piazza del Campo is known as one of the most beautiful squares in the world. It is also the site of the famous Palio horse race, which takes place twice a year. The square is also home to the Cathedral of Siena, which is held as one of the most impressive churches of Italy, owing especially to its richly decorated interiors.

As you walk through the town, one of the first things that you will notice is how well-preserved it is. Strolling the streets, you will feel as if you have returned to the end of the 13th century, when Siena was one of the greatest examples of civic, social and political organization in the whole of Europe. This is not just another Tuscan hill town, Siena has long been recognized as one of the most prestigious capitals of Europe during the middle ages.

After departing from Florence and spending the morning in Siena, you will move along to the afternoon segment of your day. Now you will tour San Gimignano, famed for its medieval skyscrapers, high walls and narrow streets that fit perfectly with what most tourists imagine of a Tuscan hill-town to be like. While in San Gimignano, you will learn about the Guelph-Ghibelline conflict and commercial interests that forced the local rich families to build their impressive and now famous towers. You will also learn what brought fortune and bankruptcy alike to this town that despite its small size is one of the most visited and unique destinations in all of Italy.

During this day tour, you will also stop in Monteriggioni, a small but nonetheless treasured jewel of the region. This walled medieval fortress which sits on top of a hill surrounded by picturesque Tuscan countryside stretching out in all directions, is a historically significant must see location. Its walls and fourteen towers have remained entirely intact, and the story of how it was built, why, and the importance that it had over the centuries will astound you.

Chauffeured Tour to Enjoy Siena, San Gimignano and not only

Siena and San Gimignano day tours from Florence start with driving from Florence to Siena, which takes about 1 hour. The drive is very scenic as the highway cuts through the outskirts of the Chianti area. Some passengers may decide to reduce their time in Siena or San Gimignano, and instead detour onto the country roads which are parallel to the highway. If you want to add Chianti to your day, then it is advised that you make your tour day at least 10-12 hours long. This will allow you plenty of time to explore one or two of the various wineries which are within reach from the highway. Almost all of them offer wine tasting, and in many cases the ability to buy a bottle to take with you.

Our vehicles are authorized to enter the city center, so you have a choice. You can either let the driver park at the entrance and you can walk to the sites, or you can just hop in and out at each location in the city center if it is more comfortable for you or if you have mobility issues.

Driver Guide or a Driver and a Local Guide?

Drivers will stay with the car, while Driver Guides will normally escort clients walking through the town with them and assisting them during the visit. Your guide will orient you and giving you relevant information about what you are visiting. Do note, however, that you will not be getting in-depth explanations, such as what a specialized guide would provide.

The San Gimignano visit normally takes 1 hour, in Siena, likewise, drivers can drive into the heart of the city if necessary, even though we prefer parking next to the main city-gate Porta San Giovanni, and letting clients walk from there by themselves or with the Driver Guide. We feel that it is a much better and more enjoyable experience for the client to walk the streets as those who came before them centuries ago did. It leads to really experiencing the place in all of its earnestness.

The amount of information that a Driver Guide provides on this tour is unquestionably more than enough to make the majority of people feel that they “learned a lot”. But if there are sights at which you want to be guided, a Local Guide is necessary. We would be happy to facilitate the hiring of a local guide should you desire one.

What our customers are saying


I want to thank you for such a wonderful vacation that my family had with your company. Our trip to Italy was one of the best we have experienced. That greatness was made in large part by the people that looked after us and toured us from place to place. I hope to travel with you again when we come back to Italy!

Jennifer L.


I just wanted to say thank you for all of your help coordinating our travel throughout our stay. We absolutely loved each of our drivers and everything was truly perfect. We will sing your praises to any and all friends who may be traveling to Italy and I hope to use your service when we can make it back there ourselves!

Anna F.


I was extremely satisfied with all aspects of our journeys from Florence to Siena and from Siena to Rome. The drivers and cars were excellent, the timing perfect and I would have no hesitation in continuing to book with you in future. Thank you for all the help with our transportation needs. Your team is so great!

Andrew D.


We had a wonderful day trip with our Driver Guide! He was polite, intelligent, considerate and extremely knowledgeable! We appreciate every consideration he showed to make our experience in Tuscany beyond our expectations. We will definitely recommend your company to our friends and use you again in future!

David B.


I just wanted to say that our driver was absolutely exceptional!! Friendly, extremely safe, efficient, punctual and very accommodating... just above and beyond in every way. He had great recommendations too (restaurants, wineries, shopping, etc) We will 100% use your services again, and highly recommend you to our friends.

Samantha C.


Our transfers from airport and all other transfers were perfect. All of the drivers we had were absolutely brilliant, attentive and welcoming as well as being on time in every case. Thank you very much for making our holiday stress-free and enjoyable. Your company is just great, and we had terrific experiences!

Phil M.