Private Tour of Siena and San Gimignano

Experience a private tour discovering Siena, San Gimignano, and the Chianti hills, among medieval villages, timeless art, and postcard-worthy landscapes.

What you can discover

Each tour is fully customizable: choose from the proposed experiences and build your unique itinerary, tailored to your desires.

SIENA

Siena welcomes you with its timeless charm: medieval streets, scenic squares, and the unmistakable warmth of a city that lives to the rhythm of tradition.

SAN GIMIGNANO

San Gimignano, with its towers challenging the sky, offers breathtaking views and an atmosphere suspended between art, history, and the aroma of Vernaccia wine.

MONTERIGGIONI

Monteriggioni, a small village enclosed by perfect walls, seems to have stepped out of an ancient tale: silent, intact, steeped in Tuscan history and poetry.

Typical Winery

Visit a typical Tuscan winery and taste fine wines while surrounded by hills, vineyards, and authentic flavors.

Tour photos

WHY CHOOSE TUSCANY EXCURSIONS

Comfort, authenticity, and freedom: travel in style with local drivers with over 10 years of experience, taste authentic flavors, and enjoy a tailor-made experience built around your desires.

Included services and extra options

What's included in the tour

WHAT'S NOT INCLUDED (UPON REQUEST)

What they say about us

Posted on Google Google
Jerrod S profile picture
Jerrod S
23 September 2026
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
We had Alessandro conduct our tour ya couple days ago and it was fantastic. Tuscany Excursions set up a great of wineries including lunch. They curated a tour based on my interests in wine and the region. Also, Alessandro was fantastic in that we had a wonderful conversation about the wine, grapes and the region history. The conversation with Alessandro was so. Helpful and informative providing us with a good contextual understanding of the area, wineries and its history. It wasn’t a tourist oriented canned presentation. We will use Tuscany Excursions again.
Posted on Tripadvisor Tripadvisor
Jerrod S profile picture
Jerrod S
23 September 2026
Tripadvisor star 1Tripadvisor star 2Tripadvisor star 3Tripadvisor star 4Tripadvisor star 5Verified
Great wine tour We had Alessandro conduct our tour ya couple days ago and it was fantastic. Tuscany Excursions set up a great of wineries including lunch. They curated a tour based on my interests in wine and the region. Also, Alessandro was fantastic in that we had a wonderful conversation about the wine, grapes and the region history. The conversation with Alessandro was so. Helpful and informative providing us with a good contextual understanding of the area, wineries and its history. It wasn’t a tourist oriented canned presentation. We will use Tuscany Excursions again.
Posted on Google Google
joshua rodgers profile picture
joshua rodgers
21 September 2026
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
Leonardo helped me craft a wonderful 8 hour day trip from Florence where my family was picked up at our door by a comfortable air conditioned Mercedes. The wineries that he suggested were wonderful with amazing wine, food and breath taking views. We would definitely engage with him again if we come back to Italy.
Posted on Google Google
Jose Triana profile picture
Jose Triana
21 September 2026
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
+11
If you're looking for personalized service in Spanish, without a doubt, contact Alessandro and his team at Tuscany Excursions. Our trip started off a bit frustrating due to the difficulty of getting around, but Alessandro made our stay in Florence wonderful. He provided a luxurious city tour, picked us up at our hotel, took us to a spectacular lunch overlooking the Tuscan countryside, and transported us in a luxurious and impeccably comfortable vehicle. Punctual, attentive, and with extensive knowledge of Florentine history, he made our stay in Florence a truly memorable experience. We wholeheartedly recommend him to anyone visiting this spectacular city of Florence and looking for service in Spanish.

(Translated by Google, see original)
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Janice M profile picture
Janice M
21 September 2026
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Day trip to Pisa and Lucca Excellent trip from Florence to Pisa and Lucca. Leonardo was very knowledgeable and a very good driver
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joshua r profile picture
joshua r
21 September 2026
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Excelllent Florence Day Trip We had an amazing 8 hour private day trip from Florence where we visited the leaning tower of pisa as well as 2 wineries. Leonardo took care of all of the scheduling with the vineyards. The day was absolutely perfect where we got great pictures, amazing wine and delicious food. I would definitely book with this operator in the future.
Posted on Tripadvisor Tripadvisor
Jose T profile picture
Jose T
21 September 2026
Tripadvisor star 1Tripadvisor star 2Tripadvisor star 3Tripadvisor star 4Tripadvisor star 5Verified
Luxury Personalized Tour in Tuscany. If you're looking for personalized service in Spanish, without a doubt contact Alessandro and his team at Tuscany Excursions. Our trip started off a bit frustrating due to the difficulty of getting around, but Alessandro made our stay in Florence wonderful. A luxury city tour, he picked us up at our hotel, took us to a spectacular lunch overlooking the Tuscan countryside, and provided transportation in a luxurious and impeccably comfortable vehicle. Punctual, attentive, and with extensive knowledge of Florentine history, he made our stay in Florence a truly memorable experience. We wholeheartedly recommend him to anyone visiting this spectacular city of Florence and looking for service in Spanish.

(Translated by Google, see original)
Posted on Google Google
Nicole Bruno profile picture
Nicole Bruno
19 September 2026
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
+4
⭐⭐⭐⭐⭐ Absolutely Fantastic Experience with Tuscany Excursions! Tuscany Excursions was nothing short of prompt, professional, personable, and knowledgeable from start to finish. Communication was excellent—from the initial email to the confirmations and questions leading up to our trip. They were always quick to respond and extremely professional. Having previously run a car service myself, I really appreciate how responsive and organized they were. The only small recommendation I would make is that they confirm with the customer the day before rather than having the customer reach out to confirm. Our driver, Leonardo, was absolutely fantastic—and I don’t use that word lightly! He was passionate, intelligent, incredibly knowledgeable, polite, and genuinely enjoyable to spend the day with. We had wonderful conversations and learned so much about the area during our drive from Florence to Siena, San Gimignano, a beautiful winery for lunch, and back to Florence. Spending a full eight hours with someone can certainly feel like a long day if the person isn’t personable, but Leonardo made the entire experience so enjoyable. We truly loved our time with him and felt like we were traveling with someone who genuinely cared about making our day special. The Mercedes van was beautiful, spotless, and extremely comfortable. Leonardo arrived early to pick us up and stayed in communication throughout the day, especially when dropping us off to explore different areas. Everything was seamless and stress-free. We highly recommend Tuscany Excursions and especially Leonardo to anyone looking for a private day trip from Florence to explore the surrounding areas of Tuscany. The service, vehicle, communication, and personal attention were all exceptional. 5 stars all around! ⭐⭐⭐⭐⭐ We would absolutely use them again!
Posted on Tripadvisor Tripadvisor
Nicole B profile picture
Nicole B
19 September 2026
Tripadvisor star 1Tripadvisor star 2Tripadvisor star 3Tripadvisor star 4Tripadvisor star 5Verified
⭐⭐⭐⭐⭐ Absolutely Fantastic Experience with Tuscany Excursions! ⭐⭐⭐⭐⭐ Absolutely Fantastic Experience with Tuscany Excursions! Tuscany Excursions was nothing short of prompt, professional, personable, and knowledgeable from start to finish. Communication was excellent—from the initial email to the confirmations and questions leading up to our trip. They were always quick to respond and extremely professional. Having previously run a car service myself, I really appreciate how responsive and organized they were. The only small recommendation I would make is that they confirm with the customer the day before rather than having the customer reach out to confirm. Our driver, Leonardo, was absolutely fantastic—and I don’t use that word lightly! He was passionate, intelligent, incredibly knowledgeable, polite, and genuinely enjoyable to spend the day with. We had wonderful conversations and learned so much about the area during our drive from Florence to Siena, San Gimignano, a beautiful winery for lunch, and back to Florence. Spending a full eight hours with someone can certainly feel like a long day if the person isn’t personable, but Leonardo made the entire experience so enjoyable. We truly loved our time with him and felt like we were traveling with someone who genuinely cared about making our day special. The Mercedes van was beautiful, spotless, and extremely comfortable. Leonardo arrived early to pick us up and stayed in communication throughout the day, especially when dropping us off to explore different areas. Everything was seamless and stress-free. We highly recommend Tuscany Excursions and especially Leonardo to anyone looking for a private day trip from Florence to explore the surrounding areas of Tuscany. The service, vehicle, communication, and personal attention were all exceptional. 5 stars all around! ⭐⭐⭐⭐⭐ We would absolutely use them again!
Posted on Google Google
Micol Cambi profile picture
Micol Cambi
14 September 2026
Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
I had an appointment at Bologna airport at 1am and he didn't show up. The next morning he sent me a message telling me he hadn't heard the alarm... awful... and this guy claims to be a professional... I'm speechless.

(Translated by Google, see original)

Frequently Asked Questions

The tour lasts about 8 hours, with the possibility of extensions upon request.

Yes, upon request we can book lunch and wine tasting at a local winery near San Gimignano

You can request it for Siena as an extra service, also available in your language.

Certainly! It’s private and flexible, designed for every need.

Pick-up takes place at your hotel in Florence or another agreed location.

BOOK YOUR Private Tour of Siena and San Gimignano

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