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

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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Off to the Races in Siena

Emanuela was excellent. She was kind and knowledgeable. We really enjoyed our laid back day seeing Siena, Tuscan countryside (with winery), and San Gimignano. The weekend we went was the horse race event and it was even more special to see the set-up and festivities for that tradition!

ankonagAug 16, 2026TRIPADVISOR

Tuscany

Driver spoke excellent English. He gave great advice on where to go in each stop. Very accommodating.

133marcyhJun 29, 2026TRIPADVISOR

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