Tuscany: Day Trip to Pisa, Siena, San Gimignano, and 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: 1 day learn more
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 renowned Piazza dei Miracoli in Pisa, Italy. Famous for its unique Romanesque design, the cathedral boasts exquisite marble facades, detailed sculptures, and an impressive bronze entrance door. Inside, visitors can admire remarkable artworks, including pulpit sculptures by Giovanni Pisano. The Duomo di Pisa is a symbol of Pisa’s rich architectural and artistic legacy, attracting visitors from across the globe.
  • Leaning Tower of Pisa - Standing nearly 56 meters tall (about 183 ft) and leaning at an angle of about 4 degrees, the Leaning Tower is one of the world’s most recognizable and iconic structures. Enjoy the moment in this globally renowned location: take creative photos or explore the nearby streets.
  • Mura di Pisa - The city walls of Pisa are historic fortifications primarily built in the 12th century to defend the city of Pisa, Italy. These walls encircled the city, featuring towers, gates, and ramparts. Over the years, the walls have been modified and expanded, showcasing a mix of architectural styles. Although some sections have been lost, parts of the walls still stand, contributing to Pisa’s historical heritage and exemplifying its medieval defensive architecture.
  • Camposanto - The Camposanto Monumentale in Pisa, Italy, is a historic cemetery established in the 12th century. Renowned for its beautiful architecture, it contains Roman and medieval sculptures, sarcophagi, and frescoes. Despite suffering damage during World War II, ongoing restoration efforts continue to preserve its cultural importance.
  • Battistero di San Giovanni - The round-shaped Baptistery, encircled by its evocative columned arcades, is a magnificent structure that complements the nearby Cathedral and Leaning Tower. Constructed over several centuries, the baptistry features a blend of Romanesque and Gothic architectural styles.
  • Via Francigena Tappa 32 San Gimignano - Monteriggioni - From Pisa, we drive past hilltop hamlets scattered across some of the most beautiful and enchanting countryside views until we reach San Gimignano, where a traditional Tuscan lunch with a tasting of four different wines will be served.
  • San Gimignano - After lunch, continue your exploration of a Tuscan medieval gem, the stunning village of San Gimignano, a UNESCO World Heritage site known for its well-preserved ancient town planning. Often called the “Manhattan of the Middle Ages,” its famous tall, narrow towers create a skyline reminiscent of a modern city.
  • Piazza della Cisterna - Piazza della Cisterna is a picturesque medieval square located in the heart of San Gimignano. Surrounded by well-preserved medieval towers and historic buildings, the square is named after the ancient cistern at its center. The triangular square, paved with medieval stones, exudes a timeless charm. With its well-preserved medieval architecture and unique allure, Piazza della Cisterna is a captivating highlight within the UNESCO World Heritage site of San Gimignano.
  • Mura di San Gimignano - These well-preserved walls, dating back to the 13th century, served both defensive and symbolic purposes. The “Mura” offer a scenic walk along their length, providing panoramic views of the charming town, its iconic towers, and the picturesque Tuscan countryside.
  • Piazza del Campo - Our final stop is Siena, reached by driving through the beautiful Chianti countryside. Siena is a remarkable hilltop town, rich in art, traditions, famous monuments, and scenic views, with a captivating pedestrianized historic center and one of the world’s most beautiful cathedrals. Upon arrival in Siena, our local guide will lead a walking tour through the narrow medieval streets and squares, passing the world’s oldest bank and the Piazza del Campo—site of the famous 600-year-old Palio horse race—on the way to the spectacular cathedral.
  • Piazza Salimbeni - The world’s oldest bank, Monte dei Paschi, is located in Siena’s Piazza Salimbeni. The Renaissance-style palace housing the bank dates back to 1523.
  • Duomo di Siena - Cathedral entrance and guided interior visit only if the option is selected. Officially known as the Cathedral of Santa Maria Assunta, this stunning medieval cathedral in Siena is renowned for its distinctive Gothic architecture and magnificent facade adorned with intricate sculptures. Inside, visitors can admire remarkable artworks, including frescoes, mosaics, and statues by renowned artists like Donatello and Michelangelo. The cathedral’s breathtaking interior also features a striking marble pavement and the magnificent Piccolomini Library.
  • Piccolomini Library - Only if the cathedral entrance option is selected. The Piccolomini Library, located within the Duomo di Siena, is a Renaissance treasure decorated with vibrant frescoes by Pinturicchio. Commissioned by Pope Pius III, these artworks depict scenes from his life, making the library a cultural and artistic gem within the Siena Cathedral.
  • Torre del Mangia - The Torre del Mangia is a striking medieval tower in the heart of Siena, Italy. Adjacent to the Palazzo Pubblico, this iconic structure offers panoramic views of the city and its surroundings. Completed in 1348, the tower stands 87 meters tall and remains a prominent symbol of Siena’s medieval heritage.
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 (except for Escorted Round Trip option)
  • Guided tour in Siena (except for Escorted Round Trip option)
  • Dedicated Staff Assistance at the meeting point
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, one of the most iconic buildings in the world.

From Pisa, drive past hilltop hamlets scattered across some of the most enchanting areas of the countryside. Arrive in San Gimignano where a Tuscan lunch with wine pairing will be served (if option selected).

Continue to the medieval village of San Gimignano, UNESCO World Heritage site nicknamed the “Manhattan of the Middle Ages” because of its towers.

End the tour in Siena. Stroll the pedestrian historical center and visit the beautiful cathedral (if option selected). Take a walking tour along the medieval streets and squares, passing the oldest bank in the world, and Piazza del Campo.

  • Comfortable shoes suggested
  • Appropriate clothing is recommended to visit places of worship
  • Please advise any specific dietary requirements at time of booking
  • It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the tour, nor to have a refund or reschedule the tour.
  • Please be advised that it is required to bring your original ID with you during the tour.
  • Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation.
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
(1216 Ratings)
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84piyushk
Sep 6, 2024
Italian Beauty - Amazing trip. Very beautiful. San Gimignano is a beautiful city. The trip guides were very helpful. Freddy specially was super helpful.
Review provided by Tripadvisor
Alexarb3401xg
Sep 6, 2024
Well organized, entertaining, and delicious! - Well organized and efficient trip. Great overview of destinations. Lunch in Tuscany was entertaining and delicious. Would recommend this tour to anyone wanting a full day expedition to Italian wine country! Federico, Alexandra, and Fernando were lovely operators.
Review provided by Tripadvisor
Sammmmyt
Sep 6, 2024
Tuscany Day Trip - Our day trip to Tuscany was incredible. Federico, Alexandra and Ferdinand were happy to help, fantastic enthusiastic guides who you can tell are really passionate about what they do. Would happily go on a tour with them again, full of knowledge as well along the way.
Review provided by Tripadvisor
Erminia_f
Sep 3, 2024
Well worth it - Great day. Pisa was amazing san Gimignano was great and gelato was good. Well Siena was outstanding we saw the culture of the contradats with the blessing of a saint parade amazing
Review provided by Viator
Clairewy3511af
Sep 2, 2024
Would recommend! - Federico was amazing! So kind and very organized. He was very clear with his direction at every stop which made for a smooth day. The tour was bilingual so he said everything single bit of information and tour guidance in both English and Spanish. Each stop was worth seeing and it felt like there was plenty of time to have a full visit. Fair warning, we opted out of some of the extra tour options (the cathedral & walking tours) so we had extra time than some others; however, Federico provided lots of recommendations that filled the time nicely. If you have the time to spend a day on a tour, I’d highly recommend this one!
Review provided by Tripadvisor
I8703pudaniels
Sep 2, 2024
Made our honeymoon even better! - The trip was a blast! The views from San Gimignano were beautiful, and the shops offered plenty to look at (and even more to buy!) check out “la torre” if you need anything leather ;) Federico was very informative every step of the way, and Ferdinand (our driver) was amazing. Our second host Alessandra was super helpful and sweet! My wife and I definitely recommend.
Review provided by Tripadvisor
803ayeshaj
Sep 2, 2024
Amazing, 5 star experience - Frederick, Alexandra and Ferdinand were our team for the day and they were fabulous! The tour was very very good and a great way to get to see three cities in the Tuscan region and an excellent mix of food, wine, shopping, history and culture. Amazing way to spend the day!
Review provided by Tripadvisor
Haow43
Sep 2, 2024
Great tour to Tuscany - Great tour to Tuscany area we took! The tour we took is for a day trip to Tuscany area. The guides are friendly and helpful!
Review provided by Tripadvisor
Y263osantonioh
Sep 2, 2024
Highly recommend ! - I went on the Tuscan tour with my girlfriend and another couple. This was truly an amazing experience !! Federico was amazing and made sure to give great information during the entire trip. He did a good job at pointing out historical facts and local stories that helped shape the significance of each stop. I would also recommend getting the lunch included with your tour, because it was fantastic. There were several wines and olive oils that we were able to try with a beautiful background of Tuscany.
Review provided by Tripadvisor
P3750pzannaw
Sep 2, 2024
Friendly team and well organised tour - Amazing views, food, wine and architecture. Federico was so friendly and helpful and gave some great recommendations at each place we stopped.
Review provided by Tripadvisor
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September 2024
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