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

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.

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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

• Escorted Round Trip – No Lunch
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  Transport with Tour Leader on board. Lunch not included
• Spanish Tour with Cathedral
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  Tour with Tour Leader on board, Guided Visit in Siena with its Cathedral admission. Typical Lunch with Wine Tasting included
• English Tour with Cathedral
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  Tour with Tour Leader on board, Guided Visit in Siena with its Cathedral admission. Typical Lunch with Wine Tasting included
• Tour in Spanish
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  Full Tour in Spanish: Tour with Tour Leader on board and Guided Visit in Siena. Typical Lunch with Wine Tasting. Cathedral admission not included
• Escorted Round Trip with Lunch
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  Transport with Tour Leader on board and typical Lunch. Siena Guided Visit and Cathedral admission not included
• Tour in English
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  Full Tour in English: Tour with Tour Leader on board and Guided Visit in Siena. Typical Lunch with Wine Tasting. Cathedral admission not included

• 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

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Meeting point and check in time:
At 07:15 am, 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. Mandatory to respect the check in time.

How to reach the Meeting Point from Santa Maria Novella Station Square:
Take “Via Valfonda”(Valfonda street) and go straight on at the end of the street, until you see the Fortress (Fortezza da Basso). Cross the street in front of you and keep your left side, until you see on the right side Piazzale Montelungo (big square with car and Bus parking)

An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.

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.

Tour in English and Tour in Spanish options do not include Siena Cathedral admission
Shared Round Trip option does not include Siena Guided Visit and Cathedral admission.

For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.

Caf Tour & Travel Agency address: via dei Tavolini 15red – 50122 Firenze – Phone +39 055 29.55.72 or +39 055 28.32.00 – Whatsapp: +39 3458025842 – email address: tours@caftours.com

Please be advised..

• This Tour is Provided by CAF Tour and Travel.
• Tour Timezone & Starts at Europe/Rome.
• Mobile or paper ticket accepted.
• For a full refund, cancel at least 24 hours before the scheduled departure time.
• This Tour is Rated 4 Stars based on 1466 valid reviews on VIATOR.
• Minimum 1 Travelers is required to book.
• Maximum 8 Travelers is accepted for booking.