Private Tuscany Tour: Pisa, Siena, San Gimignano & Winery Lunch

From€580
8 hours
Florence, Italy

About this activity

Discover Tuscany's iconic cities—Pisa, Siena, and San Gimignano—on a private tour from Florence, complete with a traditional winery lunch.

Highlights

  • Marvel at Pisa's Leaning Tower
  • Explore Siena's historic city center
  • Wander through San Gimignano's medieval streets
  • Enjoy a traditional Tuscan lunch at a winery
  • Experience the scenic Tuscan countryside

Full description

Experience the charm of Tuscany on a private tour that takes you from Florence to the iconic cities of Pisa, Siena, and San Gimignano. Begin your day marveling at Pisa's Leaning Tower and the historic Piazza dei Miracoli. In Siena, wander through its medieval streets and visit the stunning Siena Cathedral. Then, explore San Gimignano, known for its well-preserved medieval architecture and towers. Throughout the day, enjoy a traditional Tuscan lunch at a local winery, savoring regional specialties and wines. This tour offers a personalized and immersive experience of Tuscany's rich history and culture.

Included / Excluded

  • Private transportation from Florence
  • Guided tours of Pisa, Siena, and San Gimignano
  • Traditional Tuscan lunch at a local winery
  • Gratuities for the guide and driver

Important information

Know before you book

  • This is a private tour; the vehicle and guide are exclusive to your group.
  • The tour operates rain or shine; cancellations due to weather are rare.
  • Please inform the operator of any dietary restrictions in advance.

Know before you go

  • Wear comfortable walking shoes for cobblestone streets.
  • Bring a camera to capture the picturesque landscapes.
  • Check the weather forecast and dress accordingly.

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
  • Infants Required On Laps

Traveler reviews

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Lovely Day!

We had an amazing tour of the Tuscan countryside yesterday. Our guide, Alessandro, was terrific. He’s friendly and extremely knowledgeable. He was a pleasure overall. The stop in Siena was unforgettable. We had a local guide, Carlo, who was amazing. He was informative, outgoing and very passionate about his city. The lunch and wine tasting at Fattoria Poggio Alloro was exceptional. We enjoyed several excellent wines in a gorgeous setting. San Gimignano was up next. What a great spot for shopping and exploring. Finally, we got to see the tower of Pisa. Beautiful! Our driver was excellent as well. I absolutely recommend this tour to everyone!

Coppell12Sep 13, 2026TRIPADVISOR

The best Tuscany tour ever!

What a wonderful experience! Our Walkabout Florence tour to Siena, San Gimignano, a Tuscan winery, and Pisa was truly one of the highlights of our trip to Italy. The entire day was extremely well organized, and Manolo was knowledgeable, friendly, enthusiastic, and attentive throughout the tour. Our driver Sergio was so profesional. We learned so much about the history, culture, architecture, and traditions of Tuscany while also having enough time to enjoy each destination. Siena was absolutely beautiful. San Gimignano was magical—walking through its medieval streets. One of our favorite parts of the day was the winery experience. The setting was beautiful, the wine was excellent, and the lunch was delicious. Ending the day in Pisa and finally seeing the Leaning Tower in person was the perfect conclusion to an already amazing day. It is a long and full day, but absolutely worth it. I fully recommend this tour!

gildas387Sep 11, 2026TRIPADVISOR

An Unforgettable Day in Tuscany with Alessandro! ⭐️⭐️⭐️⭐️⭐️

We had the most incredible private tour of Tuscany with Alessandro! From start to finish, he was extremely knowledgeable, helpful, and genuinely so much fun to spend the day with. We had a large group of 11 kids and 8 adults, and Alessandro did an amazing job making the experience enjoyable for absolutely everyone. He kept the kids entertained while also teaching the adults so much about the history, culture, food, and wine of Tuscany. You could really tell how passionate and knowledgeable he is about the area. We visited two gorgeous wineries, both of which were absolutely amazing, and had the opportunity to experience the beauty and charm of San Gimignano. Each stop was special, and Alessandro made everything feel effortless and enjoyable. On our way back to Florence, he also arranged for us to stop in Pisa, which was the perfect way to end an already fantastic day. Seeing the Leaning Tower in person was such a memorable bonus! Alessandro went above and beyond to make sure our entire group had a wonderful time. He was incredibly accommodating, personable, and full of great information. We learned so much while having an absolute blast. If you’re looking for a private Tuscany tour, I highly recommend Alessandro! He made our day unforgettable, and we couldn’t have asked for a better guide. 🇮🇹🍷❤️

lpb127Jul 27, 2026TRIPADVISOR

Fun tour guide and very fun experience

leaning tower of pisa was awsome. great time david was a great tour guide!!

FarAway17832543498Jan 25, 2026TRIPADVISOR

A Fun-Filled Memorable Day Visiting 3 Italian Cities and a Winery

Manolo was a fantastic tour guide and Ali an excellent driver for our day long trip from Florence to Siena, Vecchio Maneggio Agriturismo, San Gimignano and Pisa. Mano is absolutely great at what he does!

Y6133RTmelissabOct 22, 2025TRIPADVISOR