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

Embark on a Tuscany Discovery Tour and explore the iconic cities of Pisa, Siena, and San Gimignano. Indulge in a traditional Tuscan lunch with wine tasting and discover the rich history and culture of these medieval gems.

Duration: 12 hours
Cancellation: 24 hours
Highlights
  • Piazza dei Miracoli - Begin the Tuscany adventure in Pisa. Upon disembarking from the coach, visitors arrive at the Field of Miracles, a lush green area highlighted by the brilliant white structures.
  • Duomo di Pisa - The Duomo di Pisa, officially the Cathedral of Santa Maria Assunta, is a splendid medieval cathedral situated in the renowned…
What's Included
  • Earphones provided during Siena Guided Tour to better enjoy your visit
  • Comfortable transport between destinations in a modern, air-conditioned bus
  • Siena Cathedral and Libreria Piccolomini entrance with guided visit (if option selected)
  • An immersive journey led by a Licensed Tour Leader
  • Typical Tuscan Lunch with wine pairing of 4 different wines…
What's Not Included
  • Leaning Tower of Pisa entry
  • Lunch not included for the without Lunch option
Additional Information

Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine. Make your way through the rolling hills as you discover the charm of Pisa, San Gimignano, and Siena.
Your first stop will be Pisa. See the cathedral, baptistery, and, of course, the famous Leaning Tower,…

Location
Piazzale Montelungo
At 07:15 am, at Piazzale Montelungo (Montelungo Square), at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(2058 Ratings)
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Aayush_s
Aug 26, 2025
Amazing service and views. - Our tour guide , Fabiana, was absolutely amazing. I travel with two elderly parents and she was more than accomodating and helped us stay with the group. The views and different tours were amazing and fun.
Review provided by Viator
Sanma38
Aug 26, 2025
Espectacular!!! - Amazing!!! Sandro was a great guide and very professional, always on time and very knowledgeable, in general the experience 100/10
Review provided by Tripadvisor
197jiajunl
Aug 26, 2025
An Unforgettable Day in Tuscany with Sandro - We had the pleasure of spending a day with Sandro, who took us around Pisa, San Gimignano, and Siena. From the start, Sandro was incredibly friendly, knowledgeable, and attentive. He shared so much history and insight about each place, making the journey not just beautiful but meaningful as well. One of the highlights was our wine tasting lunch in San Gimignano, which he recommended perfectly—it was a truly memorable experience. What stood out most was how caring Sandro was; even when we were exploring on our own, he checked in on us to make sure everything was going smoothly. Although we only spent a few hours together, it felt like we were with a good friend. We couldn’t have asked for a better guide and would highly recommend Sandro to anyone visiting the region.
Review provided by Tripadvisor
O823yjsophiew
Aug 26, 2025
Fab tour - Sandro was fantastic and very informative throughout the trip. Thank you Sandro! I will look forwards to see you again someday!
Review provided by Tripadvisor
233elket
Aug 26, 2025
Amazing tour... - Our guide Sandro is amazing and did a great job, we enjoyed the whole tour specially the wine tasting with lunch and the Sienna church
Review provided by Tripadvisor
P7638ivwayned
Aug 26, 2025
A truly wonderful experience - Sandro was an excellent tour guide with a wealth of knowledge and very funny. The tours were very good with the locations were beautiful and the lenght of time great.
Review provided by Tripadvisor
Maps07587479815
Aug 26, 2025
Fantastic Tour with Sandro! - We had an amazing tour of Pisa, San Gimignano, and Siena with Sandro. He was knowledgeable, fun, and made the history of each place come alive. Everything was well organized, and he went out of his way to make the day enjoyable and stress-free. We couldn’t have asked for a better guide highly recommended!
Review provided by Tripadvisor
Laura
Aug 26, 2025
Enjoyable tour, a lot of walking not for those that struggle - Sandro was very helpful and informative, we enjoyed the whole experience We booked for the Minimum and upgraded on the Tour and didn’t regret it
Review provided by Tripadvisor
In_smp4291kd
Aug 26, 2025
Sandro - We really liked the excursion, the bus ride between several places is very convenient! Dynamic and friendly guide!
Review provided by Tripadvisor
Michaelcn3834lq
Aug 30, 2025
Read carefully because there is no time table in the itinerary - 1. We were told it's not possible to eat or drink on the bus when we already entered. 2. We spent more time in the bus than in the cities that we were supposed to be sightseeing. (too little time in each city) 3. Our tour guide was rushing us but she wasted our time on calling everyones name and asking if they understand the instructions at arrival in each city. 4. If you want to pick the lunch and wine tasting option please be aware - portions are quite small and food is basic. Also, you'll lose one hour of your scarce time on wine presentation and lunch. One hour is just not enough for San Gimignano because the city is beautiful. 5. Siena was the most beautiful part of our trip, I would dare to say it's more beautiful than Florence. Unfortunatelly, we were robbed of our time, and we were left with almost none of our free time. The guide was fine but talked a little bit too much about architecture instead of city's history. we were left with almost no time to grab a snack or sit for a drink because of our limited time
Review provided by Tripadvisor
From $76
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).