Day trip

Florence: Siena, San Gimignano, Pisa and Chianti Grand Tour

Day trip

Florence: Siena, San Gimignano, Pisa and Chianti Grand Tour

From US$ 255.94 per person

Take the chance to discover some of the gems of Tuscany. Together with a local guide, you will escape the crowds to explore Siana, San Gimignano, and Pisa, with a stop at a Chianti winery for lunch with a wine tasting included.

About this activity

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Duration 12 hours
Check availability to see starting times.
Live tour guide
Small group
Limited to 8 participants


  • Discover the best of Tuscany in a day
  • Visit Siena, San Gimignano, and Pisa
  • Enjoy a relaxed day escaping from the crowds
  • Learn about Tuscan wine production during a wine tasting
  • Savor a typical Tuscan lunch in a boutique winery in Chianti
Full description

Starting from Florence, you will be taken to Siena by an English-speaking driver and tour leader. You will first enjoy a guided walking tour of the ancient town, which will also let you discover Piazza del Campo, the main central square where the famous Palio horse race takes place every year. You will also explore the quieter backstreets whilst learning everything about the "Contrade," the 17 Medieval city districts that compete against each other in the Palio. Your journey then continues to San Gimignano, which is renowned for its "Medieval skyscrapers", high walls, and narrow streets that typify most peoples' image of a Tuscan hill town. San Gimignano is unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls, form an unforgettable skyline.

After some free time in San Gimignano, you will reach a prestigious Chianti boutique winery. This will be the ideal setting for a relaxing break during the day, letting you savor a delicious Tuscan lunch and taste some great Chianti wines while learning about wine production. A stop in the square of the Medieval town of Impruneta will let you discover the ancient art of terracotta, this being the capital of the material and its multiple uses both in art and in construction. You can relax with beautiful views from the window as you reach Pisa and explore its famous Piazza dei Miracoli (Miracle Square).

This is a magnificent space with an incredible cathedral and baptistry, all dominated by the world-renowned Leaning Tower. Your final drive will take you back to Florence, leaving you with your eyes, mind, and heart filled by the infinite discoveries of your incredible journey.

  • Round-trip transportation from Florence in a comfortable air-conditioned minivan
  • Small-group tour
  • Professional English-speaking driver/tour leader
  • Guided walking tour of Siena with a professional English-speaking guide
  • San Gimignano visit with free time
  • Typical Tuscan lunch in a fascinating Chianti boutique winery
  • Guided winery tour and wine tasting learning about wine production
  • Medieval town visit
  • Pisa visit with a focus on Miracle Square and the Leaning Tower of Pisa (tower tickets not included)
  • Hotel pickup and drop off
  • Gratuities
  • Leaning Tower Tickets
Not suitable for
  • People with mobility impairments
  • Wheelchair users

Select participants and date



Meeting point

Meet at the local partner’s booking office, near the banks of the Arno river.

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Important information

Know before you go

  • Unfortunately, this tour is not suitable for guests with wheelchairs or with impaired mobility
  • Please note that Italy's law doesn't permit the selling of alcoholic beverage to teens under 18 years old, so clients under this age will be served non-alcoholic beverages
  • Please inform us of any food intolerances or allergies in advance
  • Comfortable clothes and shoes are highly recommended
Customer reviews

Overall rating

4.7 /5

based on 3 reviews

Review summary

  • Value for money
  • Safety
  • Service
  • Organization

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Star rating:

Excellent experience, the small group of 8 people allowed for a more personalized experience. Important: the guided tour of Siena requires heavy walking with steep ups and downs.

December 13, 2022

Good option to get to know Tuscany in one day.

Good tour is known a little of everything we just have to go for the walk through the vineyard, we need a better explanation, walk through the vineyard, learn more about this subject or know more parts of it.

October 16, 2019

A great day. Well organised.

August 27, 2019

Product ID: 242957