Tuscany Day Trip: Siena, San Gimignano, Chianti & Pisa

From€382.48
9 hours
Florence, Italy

About this activity

Experience Tuscany's charm on a private day trip from Florence, visiting Siena, San Gimignano, Chianti, and Pisa, with guided tours and wine tasting.

Highlights

  • Explore Siena's historic center
  • Visit San Gimignano's medieval towers
  • Enjoy Chianti wine tasting
  • See Pisa's Leaning Tower
  • Discover Tuscan countryside landscapes

Full description

Discover the enchanting Tuscan countryside on a private day trip from Florence. Begin in Siena, renowned for its medieval architecture and the historic Piazza del Campo. Next, wander through San Gimignano, famous for its towering medieval structures. Enjoy a delightful wine tasting in the Chianti region, savoring the area's renowned wines. Conclude your journey in Pisa, marveling at the iconic Leaning Tower and the surrounding architectural wonders. This personalized tour offers a comprehensive glimpse into Tuscany's rich heritage and scenic beauty.

Included / Excluded

  • Private transportation from Florence
  • Guided tours of Siena, San Gimignano, and Pisa
  • Wine tasting in the Chianti region
  • Meals and personal expenses

Itinerary

1

Pass by: Your day will start at your accommodation in Florence, where your private English-speaking driver, will pick you up, at the requested time.

Admission: NOT_APPLICABLE
2

Pass by: Depart Florence and during the 1 hour ride to Siena admire the famous Tuscan countryside (rolling hills, huge vineyards, olive trees, etc). Your private driver will give you an introduction about your day and you will decide the exact schedule according to your personal needs.

Admission: NOT_APPLICABLE
3

Visit Siena, one of the most beautiful city of Tuscany, full of narrow streets, medieval towers and delightful squares; admire the famous Piazza del Campo, used twice a year for the famous “Palio” horserace, the most important event in the life of the Senese people; see the most important Gothic cathedral south of the Alps, and have a look at the local shops.

Duration: 2 hoursAdmission: NOT_APPLICABLE
4

On the way to San Gimignano (approx 45 mins), if needed, your driver will suggest the best option to taste a real fresh and genuine Tuscan meal paired with the famous Chianti red wines, or if you prefer, something faster on the way. Once in San Gimignano admire the splendid skyline made up of 13 medieval towers, see the “Duomo” or Collegiata Church, the “Palazzo Nuovo del Podestà” which is now the town hall, and the infamous Museum of Torture. Shopping lovers can stroll around going in and out of the numerous specialty shops (ceramics, leather goods, linens and local products including San Gimignano’s “Vernaccia” white wine.

Duration: 1h 30mAdmission: NOT_APPLICABLE
5

Your driver will drop you off directly at Piazza dei Miracoli (Miracle Square) where you will have the chance to admire one of the finest architectural complexes in the world. The Cathedral, the Baptistery, the world famous Leaning Tower of Pisa, and the Campo Santo or Cemetery.

Duration: 1 hourAdmission: NOT_APPLICABLE
6

Pass by: Your day will ends with a relaxing 1 hour drive to your accommodation in Florence

Admission: NOT_APPLICABLE

Important information

Know before you book

  • Confirm the tour's availability on your preferred date.
  • Inform the operator of any dietary restrictions in advance.
  • Be aware that some sites may have entry fees not included in the tour price.

Know before you go

  • Wear comfortable walking shoes for cobblestone streets.
  • Bring a camera to capture 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
  • Infant Seats Available

Good to know

  • We can accommodate people using a foldable wheelchair

Traveler reviews

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The best!

What an amazing day!!!! Diego was just the sweetest and made the day perfect for us. He showed us things along the journey, took great photos, and made the day a complete breeze! Highly recommend this!!!

Shannon_KMay 24, 2026VIATOR

A Day in Tuscany!

The 10 Hour Day Trip was perfect from Start to Finish! We were picked-up from our hotel on time in a lovely, new Mercedes Van. Donnatello was our tour guide. He was friendly, worldly, sophisticated, knowledgeable and articulate. We made our way to Pisa before the crowds arrived. Donnatello made our drop-off and pick-up at Pisa easy. After one hour of touring, getting a quick coffee and delicious pastry with a gorgeous view of the Tower, we were out as the crowds flooded the area. Donnatello’s advised timing was perfect! The country-side ride to San Gimignano allowed us to understand and see the splendor of the area. Again, Donnatello’s advice of where to go in the SG Village was spot-on. We spent a glorious two hours shopping. After inquiring about our lunch preferences, Donnatello recommended a beautiful restaurant called La Locanda Di Pietracupa. The food and wine list were exceptional. The personal, family service was special. We spent a wonderful 2 hours in gastronomic heaven! Off to Siena! Donnatello drove us to the big squares where we enjoyed the crowds of locals celebrating various activities. The local flavor of fun was a highlight! On our way back to Florence, Donnatello was accommodating in allowing us to stop and see a friend at her Villa. We arrived back to Florence right on time. A perfect end to a perfect day, only made better by Donnatello!

Josephine_AMay 9, 2026VIATOR

Great day

Great day spent visiting the outskirts of Florence and great vehicle and driver. Would recommend buying Pisa tower tickets in advance. Had two teen agers and it was great. Good amount of walking.

Nancy_BApr 6, 2026VIATOR

Andrea was the greatest...

Andrea was the greatest and kindest driver and guide. We loved him, and he showed us the most special places!! We won’t forget Andrea or the day he gave us.

Zak_LApr 1, 2026VIATOR

Leo is great!

Great trip! Leo was very knowledgeable and nice! Highly recommended!! Family of 6, daughters age 10,13,15,18 had a great experience and got to see a lot. Leo kept them engaged and taught us all about Italy

Kipp_KMar 30, 2026VIATOR

Additional information

We can accommodate people using a foldable wheelchair