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

icon 12 hours Mobile ticket Free Cancellation
Tickets from € 104.00

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July 2025
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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.
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  • Earphones provided during Siena Guided Tour to better enjoy you 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
  • Leaning Tower of Pisa entry
  • Lunch not included for the without Lunch option
Departure Point

Piazzale Montelungo, Firenze FI, Italy 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.

Return Details

Piazzale Montelungo, Firenze FI, Italy 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.

  • Piazza dei Miracoli, Pisa, Italy
    Your Tuscany discovery begins with Pisa. Getting off the coach, we reach the Field of Miracles, a green grass field dominated by the dazzling white buildings
    15 minutes
  • Duomo di Pisa, Pisa, Italy
    The Duomo di Pisa, formally known as the Cathedral of Santa Maria Assunta, is a magnificent medieval cathedral located in the iconic Piazza dei Miracoli in Pisa, Italy. Renowned for its distinctive Romanesque architecture, the cathedral features stunning marble facades, intricate sculptures, and a striking bronze entrance door. The interior of the cathedral showcases impressive artwork, including pulpit sculptures by Giovanni Pisano. The Duomo di Pisa stands as a testament to Pisa's architectural and artistic heritage, drawing visitors from around the world.
    15 minutes
  • Leaning Tower of Pisa, Pisa, Italy
    The Leaning Tower is almost 56 meters tall (about 183 ft). It leans at about 4 degrees, making it one of the most famous and iconic buildings all over the world. You are in one of the most world known places: revel in it, take creative photographs or wander off down the local streets.
    15 minutes
  • Piazza dei Miracoli, 56126 Pisa PI, Italy
    Pisa city walls are historic fortifications constructed primarily in the 12th century to protect the city of Pisa, Italy. These defensive walls encompassed the city, featuring towers, gates, and ramparts. Over time, the walls underwent modifications and expansions, showcasing a blend of architectural styles. While parts of the walls have been lost, some sections still stand, contributing to Pisa's historical heritage and serving as a testament to its medieval defensive structures.
  • Camposanto, Pisa, Italy
    The Camposanto Monumentale in Pisa, Italy, is a historic cemetery built in the 12th century. Known for its stunning architecture, it houses Roman and medieval sculptures, sarcophagi, and frescoes. Despite damage during World War II, ongoing restoration efforts preserve its cultural significance.
  • Battistero di San Giovanni, Pisa, Italy
    The round- shaped Baptistery, surrounded by its suggestive columned arcades is a magnificent structure that complements the nearby Cathedral and Leaning Tower. Built over several centuries, the baptistry features a blend of Romanesque and Gothic architectural styles.
    10 minutes
  • Via Francigena Tappa 32 San Gimignano - Monteriggioni, San Gimignano, Italy
    From Pisa, we drive past hilltop hamlets scattered over some of the most beautiful and enchanting view of the countryside up to arrive at San Gimignano where a traditional Tuscan Lunch withTasting of 4 different wines, will be served.
    90 minutes
  • San Gimignano, San Gimignano, Italy
    After lunch, your visit continues to the discovery of a Tuscan medieval pearl, the stunning village of San Gimignano, Unesco world heritage, known for the ancient town planning still intact. It is often nicknamed the “Manhattan of the Middle Ages” because its famous tall, narrow towers create a skyline that looks a bit like a modern city.
    30 minutes
  • Piazza della Cisterna, San Gimignano, Italy
    Piazza della Cisterna is a charming medieval square situated in the heart of San Gimignano. Surrounded by well-preserved medieval towers and historic buildings, the square takes its name from the ancient cistern located at its center. The triangular-shaped square is paved with medieval stones and exudes a timeless atmosphere. With its well-preserved medieval architecture and unique charm, Piazza della Cisterna stands as a captivating focal point within the UNESCO World Heritage site of San Gimignano.
    30 minutes
  • Mura di San Gimignano, San Gimignano, Italy
    These well-preserved walls, dating back to the 13th century, served both defensive and symbolic purposes. The "Mura" offer a scenic stroll along their length, providing panoramic views of the charming town, its iconic towers, and the picturesque Tuscan countryside.
  • Piazza del Campo, Siena, Italy
    Our last stop is Siena, which we will reach by driving through the lovely Chianti countryside. Siena is an amazing hilltop town, rich in works of art and traditions, famous monuments and picturesque views with a fascinating pedestrianized historical center and one of the most beautiful Cathedrals in the world. Upon arrival in Siena our local guide will take you on a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo - site of the famous 600-year-old Palio horse-race, to the spectacular Cathedral.
    60 minutes
  • Piazza Salimbeni, Siena, Italy
    The world oldest Bank is "Monte dei Paschi" and it is located in Siena, Piazza Salimbeni. The Palace hosting the Bank is in renaissance style and dated back to 1523.
    15 minutes
  • Duomo di Siena, Siena, Italy
    Cathedral Entrance and inside guided visit only if option selected - officially known as the Cathedral of Santa Maria Assunta, is a stunning medieval cathedral in Siena. Renowned for its distinctive Gothic architecture, the cathedral showcases a magnificent facade adorned with intricate sculptures. Inside, visitors can marvel at remarkable works of art, including frescoes, mosaics, and statues by renowned artists like Donatello and Michelangelo. The cathedral's breathtaking interior also features a striking marble pavement and a magnificent Piccolomini Library.
    15 minutes
  • Piazza del Duomo, 8, 53100 Siena SI, Italy
    Only if cathedral entrance option is selected - The Piccolomini Library, housed within the Duomo di Siena, is a Renaissance gem adorned with vibrant frescoes by Pinturicchio. Commissioned by Pope Pius III, these artworks depict scenes from his life, creating a cultural and artistic treasure within the Siena Cathedral.
    10 minutes
  • Torre del Mangia, Siena, Italy
    The Torre del Mangia is a striking medieval tower located in the heart of Siena, Italy. Standing adjacent to the Palazzo Pubblico, this iconic structure offers panoramic views of the city and its surroundings. Completed in 1348, the tower reaches a height of 87 meters and remains a prominent symbol of Siena's medieval heritage.
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Travelers should have at least a moderate level of physical fitness
  • 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.
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
Journey26828393431
05 Jul 2025
The whole trip was so organized and so relaxed. Our bus driver Massimo was excellent, reliable, and prompt. The bus ride was smooth and comfortable and we had ample time to discover the villages. I especially enjoyed the lunch and wine tastings! It was the best wines I have had in a long time. Great and entertaining presentation by the restaurant host! San Gimignano had such beautiful views and an awesome medieval village! I also really appreciate Ricardo for his leadership and superb and interesting storytelling of the history of Florence, Pisa, Siena, and San Gimignano. He is very knowledgeable and fun to listen to and also bilingual. I also appreciate the assistant and intern, Elia, for her patience and conscientiousness, and caring attitude to make sure everybody in the group got back safe and sound. What an incredible wonderful day to spend in the countryside of Tuscany! Thank you so much!!
Michelle C
05 Jul 2025
The tour guide(Ricardo) and the driver (massimo) were bothe amazing! They helped me fix a problem with my tour no questions asked. They were also very kind which added to the experience as a whole.
K3952JHnicholash
05 Jul 2025
Views were amazing, the guide was very good and knowledgeable. The places they took us to were very interesting and cool to learn about.
This tour in Florence is organized by CAF Tour and Travel

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