Day trip

Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

4.7 / 5

91 reviews

Activity provider: CAF Tour & Travel
Day trip

Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

Activity provider: CAF Tour & Travel
Likely to sell out

From US$ 63.99 per person

Likely to sell out

Discover the rich history and art of the most iconic sights in Tuscany on a day trip from Florence. Experience Chianti's countryside landscapes as you explore Siena, San Gimignano, Chianti, and Pisa.

About this activity

Free cancellation
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Duration 12 hours
Check availability to see starting times.
Live tour guide
English, Spanish


  • Savor local flavors as you eat a Tuscan lunch at a countryside wine estate
  • Admire the depth and complexity of regional wines at a wine tasting
  • Discover the most renowned and picturesque Tuscan towns in just one day
  • Explore San Gimignano, Siena, and Pisa, with its world-famous leaning tower
  • Wander the romantic cobblestone streets of Siena led by a local guide
Full description

Spend the day discovering many of the main highlights of the Tuscan countryside on this guided tour with a traditional Italian lunch included. Make your way through the rolling hills as you discover the charm of Pisa, San Gimignano, and Siena.

Your first stop will be Pisa and the Square of Miracles. See the cathedral, baptistery, and, of course, the famous Leaning Tower. The Leaning Tower is almost 56 meters tall, about 183 feet, and leans at about 4 degrees, making it one of the most famous and iconic buildings in the world. 

From Pisa, drive past hilltop hamlets scattered across some of the most beautiful and enchanting areas of the countryside. Arrive at a family-run wine farm where a traditional Tuscan lunch and wine tasting will be served, if the option is selected.

Continue to the preserved medieval village of San Gimignano, a UNESCO World Heritage site often nicknamed the “Manhattan of the Middle Ages” because of its famous tall, narrow towers. Explore the town center and the charming craftsmen shops along the cobbled stone streets and small squares.

End the tour in Siena, a hilltop town rich in art and traditions. Stroll the pedestrian historical center and visit the beautiful local cathedral. Take a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo.

  • Roundtrip transportation from Florence
  • Tour guide
  • Guided tour in Siena (if option selected)
  • Siena Cathedral entrance fee (if option selected)
  • Lunch and wine tasting (if option selected)
  • Leaning Tower of Pisa entry

Select participants and date



Meeting point

Meet at Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with the local partner's logo on it.

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Important information

What to bring

  • Comfortable shoes

Know before you go

  • A minimum number of participants is required to confirm the tour, if this is not reached you will be offered an alternative or a full refund
  • The guided tour in Siena is available in two languages
  • For small groups of up to 8 people, the tour guide service could be replaced with an English-speaking driver-guide service, with the rest of the program remaining unchanged
  • If the Siena Cathedral cannot be visited due to religious services, a visit to the Santa Maria della Scala museum shall take its place
  • Until March 31, 2023, it will not be possible to visit the monuments in Pisa due to the winter schedule
  • The order of site visits may change
  • Starting April 1, 2023, Lunch with Wine tasting will be served in a characteristic Restaurant located along the ancient medieval road that led pilgrims to Rome crossing Tuscany, the famous "Via Francigena".
Customer reviews

Overall rating

4.7 /5

based on 91 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Service

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Sandro provided an excellent overview of the trip and was an awesome tour guide. He was accommodating when we needed to go find a toilet when we missed to find the one in Pisa. And he was nice in finding a chocolate candy store that gave us sample treats in our short time in San Guiminiano.

March 29, 2023

We are glad to have had the opportunity to visit these other towns, each came with a good historical narration plus interesting sights to visit. Paula was a great host, kept the journey entertaining with anecdotes and tips. Enjoyed the lunch and surprise wine tasting.

March 29, 2023

Excellent trip with CEF tour company. It was very well organized . My husband and I enjoyed the trip so much. Our tour guide Maria Louisa did a wonderful job. She always make sure everyone of us are ok. Thank you for making our trip so fun and telling the historical background in details ! The trip time management was perfect .Our tour started and finished on time . We managed to visit all sites😄 Lunch was great . We had 4 types of wine , tasted the local truffles olive oils and pasta. It was delicious and beyond our expectation. For those who wanted to visit Florence outskirts, this is definitely a great choice that worth the money. Glad we made a right decision . Thank you for making our Italy trip so wonderful!Gracias!

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March 29, 2023

Product ID: 410236