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

From€580
9 hours
Florence, Italy

About this activity

Discover Tuscany's gems on a private day trip from Florence, including Siena, Pisa, Chianti, and San Gimignano, with guided tours and wine tasting.

Highlights

  • Explore Siena's historic center
  • Visit the Leaning Tower of Pisa
  • Enjoy a scenic Chianti wine tasting
  • Wander through San Gimignano's medieval streets
  • Experience Tuscany's picturesque landscapes

Full description

Experience the best of Tuscany on a private day trip from Florence. Begin in Siena, renowned for its medieval architecture and the famous Piazza del Campo. Next, marvel at the Leaning Tower of Pisa and the Cathedral in the Piazza dei Miracoli. In the Chianti region, indulge in a wine tasting session amidst rolling vineyards. Conclude in San Gimignano, a UNESCO World Heritage site, known for its medieval towers and charming streets. This tour offers a comprehensive glimpse into Tuscany's rich history, culture, and culinary delights.

Included / Excluded

  • Private transportation from Florence
  • Guided tours of Siena, Pisa, Chianti, and San Gimignano
  • Wine tasting in the Chianti region
  • Meals and beverages not specified in the itinerary

Important information

Know before you book

  • This is a private tour; the price is per group, not per person.
  • Confirm the pickup location and time with the tour operator 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 the stunning landscapes and architecture.
  • 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
  • Infant Seats Available

Traveler reviews

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A Fabulous Day in Tuscany

Today we spent an incredible 10 hours on a private tour with Ciao Florence Tours and Travels, and it absolutely did not disappoint! Our driver, Cristian, was fantastic. He was friendly, knowledgeable, and shared the history of every place we visited, which made the day even more special. Each winery was better than the last, and we enjoyed a delicious lunch at Teruzzi Winery. It was a perfect day in Tuscany and an experience we will always remember. Highly recommend!

H184SVtinafJul 6, 2026TRIPADVISOR

My family and I had an amazing tour!!

Christian was an amazing driver with a rich knowledge of the history of Florence! We booked a tour from 8:30-5, and there was never a dull moment. He was friendly and had amazing recommendations for food, gelato, and photo opportunities. My family and I had a great time.

jadaw318May 30, 2026TRIPADVISOR

Enjoyable time in Tuscany

We found Cris prompt, knowledgeable, enthusiastic, down to earth and very receptive to what we wanted in our tour. He really took good care of us. He slightly adjusted our tour to meet our needs and interests. Whenever possible, he took us the most scenic way to enjoy the Tuscan countryside. If our future guides during the rest of our time in Italy are half as good as Cris, we will continue to have a wonderful time! Bruce S & Ann H

Ann HMay 19, 2026TRIPADVISOR

One of the best tours...

One of the best tours with a fantastic vineyard tour and lunch! Punctual with probably the best guide who made this trip efficient and memorable with two toddlers!

Yousuf_AMay 2, 2026VIATOR

A Must!!!! Fabulous

Christin was the most amazing guide!!! We had him for 10 hrs and it was outstanding!!! Christin also Went out of his way to find me the most amazing olive oil!!!

Patricia_VApr 7, 2026VIATOR