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 - Your journey through Tuscany starts in Pisa. Upon disembarking from the coach, we arrive at the Field of Miracles, a lush green expanse highlighted by its stunning white structures.
  • Duomo di Pisa - The Duomo di Pisa, officially the Cathedral of Santa Maria Assunta, is a breathtaking medieval cathedral situated in the…
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
(1927 Ratings)
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Explore50028860957
Jun 15, 2025
Pisa, San Gimignano and Sienna is a must!! - Alexendra, Julia and Eliss were really great as tour guides. They were giving us detailed explanation about the places we visited which were Pisa, San Gimignano and Sienna. The places were so majestic. Literally felt like we are born in the mediaeval era.
Review provided by Tripadvisor
Getaway45144
Jun 15, 2025
Terrific Italian Trio - The tour was wonderful! Our tour guide Alexandra was the best. She was so friendly, informative, and accommodating. Accompanied by Julia and driver Elis, they made the prefect trio. Pisa is a must see in Italy. The lunch in San Gimignano was delicious. The wine pairing was perfect and the restaurant host gave a great description of the meal. The town of Siena was so interesting and different with a cool history and great architecture. The cathedral was beautiful inside and out. I highly recommend this tour!!
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Louise_g
Jun 12, 2025
A beautiful day in Cinque Terre - It was a beautiful day to explore the mountainous region of Cinque Terre. Although our guide's microphone was not working, he would gather us close in order to explain the history of this area. Lunch was great and the boat ride back to La Spezia was very enjoyable, allowing us to view the various towns along the coast. Also, since the bus trip was long, we made coffee and rest stops along the way.
Review provided by Viator
Pizicato2000
Jun 11, 2025
Tour to Tuscany - The guides, Carby and Hilary were knowledgeable and provided clear instructions for the trip. Did the coach tour and was sufficient to have a touch and go of the Tuscany region.
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E4548eamaris
Jun 11, 2025
We love the walk - Very good walk. Fabi and Hilaria who are the guides are very attentive and funny. We love it! The places are beautiful and the time was enough to get to know. I liked the Tuscany lunch experience.
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Zad0thv
Jun 11, 2025
A perfect day under the Tuscan sun - It was my favorite experience here in Italy. The city of San Gimignano was absolutely stunning and spectacular! What a wonderful tour. I don’t know if I’d do the lunch and wine tasting again because it didn’t leave much time for exploring the city. But regardless, it was worth it. Thank you to our guides because they were kind, helpful, and informative. Would 100% recommend.
Review provided by Tripadvisor
Esteban
Jun 10, 2025
Visit to Tuscany - Very good experience! Get to know beautiful stories and places It's a long journey, but it's worth it. Do not stop entering the Siena Cathedra
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963sasham
Jun 10, 2025
Good Way to See Tuscany’s Highlights, But Be Prepared for Long Bus Rides and Lots of Walking - We booked this full-day tour to see some of Tuscany’s iconic locations — Pisa, Siena, and San Gimignano. Overall, it was a good experience, but there are some things to keep in mind. The tour starts early (before 8 AM) and finishes around 7 PM, and a good chunk of the day is spent on the bus traveling between cities. The guides, Alexandra and Federico, were friendly and knowledgeable, and the itinerary covers a lot, but some aspects could have been better planned. At each stop, there’s a fairly long walk (12–15 minutes) from the bus to the actual destination, which takes time away from exploring. In Pisa, for example, other tours seemed to have pre-arranged trolleys that dropped guests closer to the main square, which would have been appreciated. Pisa itself is worth visiting, though! San Gimignano is absolutely stunning, but I wouldn’t recommend choosing the lunch add-on. The wine tasting was minimal, and the pasta was a very basic ziti — nothing memorable. It felt more like a tourist trap aimed at getting guests to buy wine from the restaurant. That time would have been much better spent enjoying the beautiful town and grabbing lunch at a local spot with a view. If you go, skip the tour lunch and explore on your own — it’s worth it. Siena was lovely and also worth the visit, but like the other stops, the walk from the bus was a bit of a trek and cut into our time there. Lastly, a quick note about the bus ride — our driver, Jenny, got us everywhere on time, but being on the top level of a double-decker bus made some turns and speeds feel sharper than expected. Just something to be aware of if you’re sensitive to motion. In summary: a good tour for hitting the highlights if you’re short on time, but expect a lot of bus travel and walking. With a few small changes (like improving logistics and offering more flexible food options), this could have been a great experience.
Review provided by Tripadvisor
Ann_d
Jun 14, 2025
Over 20,000 steps of walking- parks far from sites - The good: The hosts were knowledgeable and these are good sites to visit. The bad: the buses park a long way away from sites. Up to a mile walking at last site. If you have knee or mobility issues this is a problem. Before we even got off the bus the hosts were walking way ahead of us- and they walk fast- even up all the hills in 91+ degree weather. So that was bad. We learned at the end of the second stop to tell them we will leave ten minutes early to head back to bus. They still caught up to us and overtook us. The last stop they got a taxi for us to meet in town square (12Euros) while they walked from bus to center. But the cathedral was still up hill and a long way. We were exhausted from the heat and the walking. Over 20,000 steps ( if you count steps). The hosts saw our issues with not walking fast like them and they were nice enough to give us a head start before they headed back to bus.
Review provided by Viator
Ianmc3460eq
Jun 13, 2025
A Long Hot Tour ! - I've done many GYG TOURS, which have been awesome. On this occasion they missed the mark. 74 people did a 12 hour tour on a double decker bus. Comfortable bus, nice bus ride, great driver. The guides appeared organised in terms of roll call etc. We did not receive radio or ear pieces. As we were seated upstairs on the bus It was difficult to hear any commentary clearly. In fact at times I thought the bus tour narration was a fellow passengers talking to family on their phone, - it was that soft and unclear. Too many tour options withln the tour group, which meant those who did not choose tour guide options on certain stops did not have any guidance or pamphlets to provide information on the visited sights. In hot weather I feel the tour is way too long as we had to walk a fair distance from where the bus stops. Also a bit more gusto/ enthusiasm would have helped - but maybe the guides succumbed to the heat as well.
Review provided by Tripadvisor
From $75
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).