Private Tour
Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence
Overview
Available languages
8 hours
Mobile ticket
Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your hotel and whisk you to the lush green hills of Tuscany. Your first stop will be San Gimignano, a beautiful and picturesque medieval town known for its many towers and gorgeous views. Then, stop at a marvelous local winery nestled in the Tuscan countryside. Enjoy a light lunch with a selection of locally produced wines, followed by a tour of the vineyard. With your taste buds still in heaven from the delicious wine and food you enjoyed, hop back on your private luxury drive to Siena. Here, your private driver will share a few stories and anecdotes and give you time to explore on your own.
If you are looking for a bit more in depth knowledge about Siena and San Gimignano, upgrade your tour by choosing the option with Private Tour Guide, who will accompany you throughout the entire day.
The day will end with a relaxing drive back to your hotel in Florence.
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
San Gimignano
Wake up in Florence and get ready for your day of exploration to begin. Your first stop will be San Gimignano, so sit back and enjoy a 90 minute private drive in a comfortable luxury vehicle. Your driver will add to the scenery by sharing stories, gossip and anecdotes about the estates and villas you pass along the way. The marvelous Medieval hill town of San Gimignano, located in the province of Siena, is currently on the list of UNESCO world heritage sites. San Gimignano or “Town of Towers” is famous for its unique and outstanding architecture. As you enter the fortified walls of the city you will learn about the famous towers and delight in the history of this picturesque town. Once there, you will be dropped off so to allow you free time to walk around the village and explore on your own. Your visit will be enhanced by the fun facts and stories your driver will share before dropping you off.
Siena
Your driver will take you across the valley to a typical Tuscan winery. Originally an ancient convent, this stunning property has been transformed into an outstanding winery and farm, where you will enjoy a nice glass of wine and some traditional food. You will then get a personal tour of the winery. Your Tuscany Day Trip continues to Siena, another highlight of Tuscany. In Siena, your private driver will guide you from site to site while sharing the elaborate history and intriguing stories of the city, and giving you free time to explore each site on the tour. Siena too is a Unesco heritage site. Every building and every corner of this quaint yet bustling town tells stories of bygone eras. And of course, you will also stop at the world-famous Piazza del Campo. Hear fantastical stories of the history of Piazza del Campo and then hop off to take delight in this shell shaped square, imagining the crowds that gather to watch Il Palio, the famous horse race that take place twice a year.
What‘s Included
Enjoy an exclusive and luxurious car ride through the Tuscan Hills
Option to add-on a Full-Day Private Guide on board (choose the option with private guide)
Non-alcoholic beverages available during the lunch
Visit San Gimignano & Siena, both UNESCO world heritage sites
Delight in Lunch and Wine Tasting in the Tuscan hills, near San Gimignano
Round trip All-day Private Chaffeur from and back to your hotel in Florence
Gratuities
Pickup points
Select a pickup point
Options
Option with Private Guide
Full Day Private Guide: This option includes a Private Tour Guide on board who will be with you the entire day.
Pickup included
Option Without Guide
Private Chaffeur without guide: This option includes the private chaffeur but it does NOT include a Full Day Private Tour Guide.
Pickup included
Reviews
31 reviews
Total reviews and rating from Viator & Tripadvisor
Favorite Day of Our Entire Italy Trip
Resort677955,Apr 5, 2026
- Review from Tripadvisor
5.00This was our favorite day of our entire Italy trip. The Siena and San Gimignano tour was outstanding, and Gabrielle made it even better. He is such a kind and genuine person, and you can tell he truly cares about the experience his guests have. One thing that really stood out was how easy he was to understand. His English pronunciation was excellent, which made a big difference in being able to fully enjoy and follow everything throughout the day. The day itself was perfectly structured. We started with exploring and shopping in Siena, then moved into a private wine tasting with a great lunch, and finished in San Gimignano with more time to walk around and enjoy the town. It never felt rushed and flowed really well from start to finish. If you are considering a day trip from Florence, this is a must. It was a true highlight of our trip.
Beautiful day
K8157UTryanp,Mar 20, 2026
- Review from Tripadvisor
5.00Great guide and tour! Lovely day!
Tour in Tuscany
Sherry H,Mar 8, 2026
- Review from Tripadvisor
5.00Where to even begin? We spent the entire day driving from Florence to the Tuscany area with stops in Siena and San Gimignano. Mattio was our fabulous driver and Rafaella was our fearless leader. The weather was cool but beautiful. Not enough words to describe the Tuscan region but I can chat about our tour. Rafaella’s knowledge of landmark’s, history of the region and descriptions of building is second to none. She has an outsized personality and is always smiling and happy. She manages an excellent team in Florence. Her local knowledge and ability to explain the customs of the region was phenomenal. She made us feel like part of her family.
Wow. If you’re on the fence about booking this, do it, you will not regret it!
Joe B,Oct 28, 2025
- Review from Tripadvisor
5.00One of the highlights of our honeymoon. We had the best day with our guide Emanuela and driver Leonardo. We are in our late 30’s/early 40’s and had a fun, enriching day learning the ins and outs of Siena and San Giamignano with Emanuela. She is a fount of knowledge, and covered everything from the academic and historical to the modern culture and society, and delivered it all with an incredible amount of passion and thoughtfulness. It was like hanging out with your favorite college professor, or history buff aunt! We only wish we had her for more of our trip! To top it off, we had an incredible lunch and wine/olive oil tasting at a local vineyard/agriturismo, a spot we would’ve have found ourselves, but was absolutely incredible. So much so that we ended up ordering wine to be delivered home - a service the vineyard smartly provided! All in all an incredible tour, worthwhile, and with great company. Thank you Emanuela, Leonardo, and LivTours!
Family trip in italy
Judith G,Jun 26, 2025
- Review from Viator
5.00Out drivers were on time and informative in the area we visited ! I would use Liv Tours again. The vans were very clean
A must do. Perfect day in the country.
Jenn26NYC,May 26, 2025
- Review from Tripadvisor
5.00Perfect day. We spent enough time in the towns. And a fabulous lunch with wine tasting on the countryside overlooking San giamignano. Our driver Lorenzo, was wonderful. Knowledgeable, funny, caring and kind. He was perfectly fantastic!
Outstanding day trip in...
Kristine G,Apr 14, 2025
- Review from Viator
5.00Outstanding day trip in the Tuscan countryside. Sienna and San Gimignano are so cute and we had a lot of fun exploring. Mattia is an excellent guide
Perfect way to see Siena
jamietetro,Mar 27, 2025
- Review from Tripadvisor
5.00We did a walking tour of Siena with Giulia and loved every minute. Since she is from there, she gave us a really special overview which our 9 and 12 year olds loved. They are still talking about that tour in particular. Siena is just breathtaking!
Tuscany day trip
GrandTour25873,Mar 18, 2025
- Review from Tripadvisor
5.00Raffi and Alasandro were fantastic. I highly recommend this day trip to the Tuscany Region. The small town tours were amazing and the stop at the winery for lunch as incredible.
10 out of 10 would recommend
Catherine S,Dec 29, 2024
- Review from Viator
5.00Worth it. Prompt and friendly service. Takes the hassle out of the coordination and allows you to relax and safely travel to the country side.
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