Exclusive Tuscany Day Trip: Siena & San Gimignano

From€550
8 hours
Florence, Italy

About this activity

Experience the charm of Tuscany with a private day trip from Florence, visiting Siena's historic center and San Gimignano's iconic towers, complemented by a local wine tasting.

Highlights

  • Explore Siena's historic center
  • Visit the iconic San Gimignano towers
  • Enjoy a scenic drive through Tuscan countryside
  • Experience authentic Tuscan cuisine
  • Discover local art and architecture

Full description

Discover the enchanting beauty of Tuscany on this exclusive day trip from Florence. Begin with a scenic drive through the picturesque Tuscan countryside, arriving in Siena, renowned for its medieval architecture and the famous Piazza del Campo. Explore the city's rich history with a guided tour, then proceed to San Gimignano, known for its medieval towers and charming streets. Enjoy a wine tasting at a local vineyard, savoring the region's renowned Chianti wines. This personalized experience offers a perfect blend of history, culture, and gastronomy, ensuring a memorable day in Tuscany.

Included / Excluded

  • Private transportation from Florence
  • Guided tours of Siena and San Gimignano
  • Wine tasting at a local vineyard
  • Meals and personal expenses

Itinerary

1

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.

Duration: 2h 30mAdmission: NOT_APPLICABLE
2

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.

Duration: 3h 30mAdmission: NOT_APPLICABLE

Important information

Know before you book

  • Private tour suitable for small groups
  • Wine tasting included; additional purchases at own expense
  • Tour operates rain or shine; dress appropriately for weather conditions

Know before you go

  • Wear comfortable walking shoes for cobblestone streets
  • Bring a camera to capture scenic views
  • Carry a bottle of water to stay hydrated

Cancellation policy

Free cancellation up to 1 days before the activity starts

For a full refund, cancel at least 24 hours before the scheduled departure time.

Accessibility

  • Stroller Accessible
  • Easy Public Transport
  • Infant Seats Available

Traveler reviews

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Favorite Day of Our Entire Italy Trip

This 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.

Resort677955Apr 5, 2026TRIPADVISOR

Beautiful day

Great guide and tour! Lovely day!

K8157UTryanpMar 20, 2026TRIPADVISOR

Tour in Tuscany

Where 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.

Sherry HMar 8, 2026TRIPADVISOR

Wow. If you’re on the fence about booking this, do it, you will not regret it!

One 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!

Joe BOct 28, 2025TRIPADVISOR

Family trip in italy

Out drivers were on time and informative in the area we visited ! I would use Liv Tours again. The vans were very clean

Judith_GJun 26, 2025VIATOR