Tuscany Tour: San Gimignano & Siena Adventure

Embark on a private day trip from Florence to Siena and San Gimignano in Tuscany. Explore medieval towns, visit a local winery, and enjoy a delicious lunch with locally produced wines.

Duration: 8 hours
Cancellation: 24 hours
Highlights
  • San Gimignano - Begin your day in Florence, ready for an exciting journey. Your first destination is San Gimignano, reached via a 90-minute private drive in a luxurious vehicle. Enjoy the ride as your driver shares fascinating stories, gossip, and anecdotes about the estates and villas you pass.
    The enchanting Medieval hill town of San Gimignano,…
What's Included
  • All-day private chauffeur for round-trip transportation from your hotel in Florence
  • Exclusive car trip through the scenic Tuscan Hills
  • Visit San Gimignano & Siena, UNESCO world heritage sites
  • Opportunity to add a full-day private guide for an enriched experience
  • Lunch and wine tasting at a picturesque location in the Tuscan hills
  • Availability of non-alcoholic beverages during lunch
What's Not Included
  • Gratuities
Additional Information

Have you always imagined yourself in Tuscany? This tour then, is specially crafted for your dream. Begin your morning in Florence and meet your personal chauffeur at your place of stay, who will transport you to the verdant hillsides of Tuscany. Your journey will lead you first to San Gimignano, a stunning medieval town, known for its numerous towers…

Location
San Gimignano
Cancellation Policy

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

Customer Ratings
5.0
(31 Ratings)
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Resort677955
Apr 5, 2026
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.
Review provided by Tripadvisor
K8157utryanp
Mar 20, 2026
Beautiful day - Great guide and tour! Lovely day!
Review provided by Tripadvisor
Sherry
Mar 8, 2026
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.
Review provided by Tripadvisor
Joe
Oct 28, 2025
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!
Review provided by Tripadvisor
Judith_g
Jun 26, 2025
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
Review provided by Viator
Jenn26nyc
May 26, 2025
A must do. Perfect day in the country. - Perfect 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!
Review provided by Tripadvisor
Kristine_g
Apr 14, 2025
Outstanding day trip in... - Outstanding 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
Review provided by Viator
Jamietetro
Mar 27, 2025
Perfect way to see Siena - We 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!
Review provided by Tripadvisor
Grandtour25873
Mar 18, 2025
Tuscany day trip - Raffi 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.
Review provided by Tripadvisor
Catherine_s
Dec 29, 2024
10 out of 10 would recommend - Worth it. Prompt and friendly service. Takes the hassle out of the coordination and allows you to relax and safely travel to the country side.
Review provided by Viator
From $468
up to 15 guests
2 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).