Tuscany Day Trip: Siena, Pisa, Chianti & San Gimignano
From€580
9 hours
Florence, Italy
About this activity
Discover Tuscany's gems on a private day trip from Florence, including Siena, Pisa, Chianti, and San Gimignano, with guided tours and wine tasting.
Highlights
- Explore Siena's historic center
- Visit the Leaning Tower of Pisa
- Enjoy a scenic Chianti wine tasting
- Wander through San Gimignano's medieval streets
- Experience Tuscany's picturesque landscapes
Full description
Experience the best of Tuscany on a private day trip from Florence. Begin in Siena, renowned for its medieval architecture and the famous Piazza del Campo. Next, marvel at the Leaning Tower of Pisa and the Cathedral in the Piazza dei Miracoli. In the Chianti region, indulge in a wine tasting session amidst rolling vineyards. Conclude in San Gimignano, a UNESCO World Heritage site, known for its medieval towers and charming streets. This tour offers a comprehensive glimpse into Tuscany's rich history, culture, and culinary delights.
Included / Excluded
- Private transportation from Florence
- Guided tours of Siena, Pisa, Chianti, and San Gimignano
- Wine tasting in the Chianti region
- Meals and beverages not specified in the itinerary
Itinerary
1
Begin your journey through the heart of Tuscany in absolute comfort… A private driver will pick you up directly from your accommodation in a luxury Mercedes vehicle. Then, you will be on your way, driving through the spellbinding scenery of Tuscany with its vibrant greenery, hilltop towns, and countless vineyards. You will arrive in Siena in about an hour.
Duration: 1 hourAdmission: NOT_APPLICABLE
2
Your driver will drop you off very close to the Siena Cathedral, a major perk of arriving in a private vehicle! Siena is a hidden gem of medieval glory in the Tuscany region. With a rich history of architecture, art, and culture, Siena itself is a UNESCO World Heritage Site. Enjoy two hours of exploration throughout the beautiful buildings, artisanal shops, award winning restaurants, and picturesque alleyways.
Duration: 2 hoursAdmission: NOT_APPLICABLE
3
While discovering Siena, you will inevitably find your way to the most famous square in the city - Piazza del Campo. Not only is this piazza a popular place for locals to gather, but it is also home to an annual palio horse race, which is an epic competition between the different neighborhoods of Siena! After admiring the panoramic views of this large, shell shaped square, you will have free time to grab a cappuccino at one of the many cafes lining Piazza del Campo, experiencing Siena as the locals do.
Duration: 1 hourAdmission: NOT_APPLICABLE
4
Rising above Piazza del Campo, you can find Torre del Mangia, the intriguing clock tower of Siena. This incredible tower dominates the city's skyline and is the third tallest tower in all of Italy! Interestingly, the tower was built to be the exact same height as the Siena Cathedral. If you are looking for unique views of the city and Cathedral, climbing the tower is a great way to discover the beauty of Siena. Entrance is not included in this tour.
Duration: 30 minAdmission: NOT_APPLICABLE
5
Make your way to the beating heart of Siena - the Siena Cathedral. At first sight, you will notice the breathtaking facade and its various colored marbles and a unique example of Romanesque-Gothic architecture. Inside, you will immediately be amazed by the incredible marble, mosaic floors, which depict biblical stories on 56 different scenes. As you look up, you will see masterpieces throughout the church from Renaissance masters including Donatello, Pisano, Pinturicchio, and Michelangelo. Walk through the breathtaking atmosphere inside, and don't forget to stop in the striking Piccolomini Library on your way out! Entrance is included in the price of this tour.
Duration: 30 minAdmission: NO
6
After a captivating morning of exploration in Siena, you can relax in the backseat of the air conditioned, luxury vehicle. Your driver will take you to San Gimignano along some of the most picturesque streets in Italy. Scenes that you have only seen in postcards will truly come to life! On this private tour, you have the perk of being able to ask your driver to stop as you prefer, so you can take incredible photos that will remain in your memory forever.
Duration: 30 minAdmission: NOT_APPLICABLE
7
From a distance, you will begin to see San Gimignano, with its unmistakable medieval “skyscrapers.” Sometimes called a medieval Manhattan, there are still thirteen towers intact in this perfectly preserved hilltop town. Your driver will drop you off outside the ancient gate of the city, and where you can find a famous panoramic viewpoint of the Tuscan countryside. You will have an hour to explore the lovely town of San Gimignano as you please.
Duration: 1 hourAdmission: NOT_APPLICABLE
8
As you wander through the characteristic alleyways of San Gimignano, the streets will lead you to Piazza della Cisterna. This is the main square of the city, and where you can find the Cathedral, Duomo, and striking medieval architecture! You can grab a gelato or a coffee during your free time while enjoying the lovely views of this Renaissance city.
Duration: 15 minAdmission: NOT_APPLICABLE
9
During your free time in San Gimignano, discover the historic Cathedral and Duomo. Inside, you can find ancient and beautiful frescoes colorfully decorating the walls of the Cathedral. Many tourists skip entering this sacred church, and it is truly a hidden gem in the center of the town.
Duration: 15 minAdmission: NO
10
After exploring the timeless beauty of San Gimignano, it will be time to depart for a great symbol of Italy - Pisa! The drive will last about an hour, as you travel in complete comfort.
Duration: 1 hourAdmission: NOT_APPLICABLE
11
With the Leaning Tower right in front of you, a visit inside will be irresistible! Enhance your experience in Pisa by making your way to the top of the Leaning Tower. From the peak, you can admire the stunning and diverse views of Pisa from above the rooftops of these ancient buildings. Enjoy the breeze on your skin, and then take some fun photos before heading back down! Admission fee is not included.
Duration: 30 minAdmission: NO
12
In the center of Piazza dei Miracoli, you will find the Cathedral of Pisa. Often overlooked by the Leaning Tower, this church is a hidden gem of pure beauty in Tuscany. The Cathedral is one of the first examples of “Pisan Romanesque” architecture, a form of design only found in Pisa and towns nearby. Discover the intricate carvings on the facade of the building, so precise it is almost unbelievable this was completed over almost a thousand years ago. Enter the Cathedral for truly heavenly views: Cimabue’s iconic fresches, Giovanni Pisano’s pulpit, and golden ceilings.
Duration: 30 minAdmission: NOT_APPLICABLE
13
After grabbing some last minute souvenirs from Pisa, hop into the backseat of your comfortable, private vehicle, and you will be on your way. Enjoy the return drive in the comfort of a private, luxury vehicle. The drive will take about one hour, and you will be dropped off at your accommodation in Florence.
Duration: 1 hourAdmission: NOT_APPLICABLE
Important information
Know before you book
- This is a private tour; the price is per group, not per person.
- Confirm the pickup location and time with the tour operator in advance.
- Be aware that some sites may have entry fees not included in the tour price.
Know before you go
- Wear comfortable walking shoes for cobblestone streets.
- Bring a camera to capture the stunning landscapes and architecture.
- Check the weather forecast and dress accordingly.
Cancellation policy
Free cancellation up to 1 days before the activity starts
For a full refund, cancel at least 24 hours before the scheduled departure time.
Accessibility
- Stroller Accessible
- Easy Public Transport
- Infants Required On Laps
- Infant Seats Available
Traveler reviews
4.8147 reviews
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Enjoyable time in Tuscany
We found Cris prompt, knowledgeable, enthusiastic, down to earth and very receptive to what we wanted in our tour. He really took good care of us. He slightly adjusted our tour to meet our needs and interests. Whenever possible, he took us the most scenic way to enjoy the Tuscan countryside. If our future guides during the rest of our time in Italy are half as good as Cris, we will continue to have a wonderful time! Bruce S & Ann H
Ann HMay 19, 2026TRIPADVISOR
One of the best tours...
One of the best tours with a fantastic vineyard tour and lunch! Punctual with probably the best guide who made this trip efficient and memorable with two toddlers!
Yousuf_AMay 2, 2026VIATOR
A Must!!!! Fabulous
Christin was the most amazing guide!!! We had him for 10 hrs and it was outstanding!!! Christin also Went out of his way to find me the most amazing olive oil!!!
Patricia_VApr 7, 2026VIATOR
An incredible private...
An incredible private tour that made exploring Tuscany effortless and memorable. Visiting the iconic Leaning Tower of Pisa was a highlight, and the charm of Siena and San Gimignano truly stood out. The guide was knowledgeable, friendly, and kept the day perfectly paced while sharing great insights along the way. Traveling by private car made everything comfortable and seamless. Highly recommend for anyone wanting to experience the beauty of Tuscany in a relaxed, personalized way!
Manoj_PMar 29, 2026VIATOR
Tuscan Super Man
If you are looking for the man who knows everyone in Florence, just call Placido. Placido was super and provided a wealth of information about Florence and Tuscany. What a great experience and a fun day. Top notch tour and Placido went above and beyond to make our day WONDERFUL. Thank you Placido from Georgia. We will call soon.
George_VSep 7, 2025VIATOR