Pisa, Siena, and San Gimignano Day Trip from Florence with Tuscan Lunch
Tour Siena Cathedral, see the Leaning Tower, dine at a Chianti vineyard, and explore San Gimignano
Searching for the ultimate day trip from Florence? On this unforgettable tour through Tuscany, take a guided walk through the medieval city of Siena, visit a Chianti vineyard for a decadent wine tasting and traditional Tuscan lunch, wander around the enchanting town of San Gimignano, and get a close-up look at the Leaning Tower of Pisa! With comfortable, round-trip transportation included and a knowledgeable guide leading the way, this is the best way to discover all that Tuscany has to offer!
What You Get With This Tour
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See Tuscany's best in one day
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Expert English-speaking guide
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Round-trip coach transportation from Florence
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Guided tour of Siena
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Entry to Duomo di Siena
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Tuscan winery lunch
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Wine tasting with Chianti, Vernaccia, and Vin Santo
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Free time in San Gimignano
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Free time in Pisa
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Leaning Tower of Pisa entry tickets
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Guide tips
Tour Itinerary
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1
Meet your guide at Santa Maria Novella train station
Your day begins outside Florence's main train station, where your guide will be waiting with a sign. Board an air-conditioned coach and settle in as the cityscape gives way to cypress-lined roads and vineyard-covered hills. -
2
Explore Siena with a guided walking tour
First, you'll arrive in Siena, a medieval city built on three hills in southern Tuscany. Follow your guide through narrow brick lanes to the shell-shaped Piazza del Campo, then step inside the Duomo di Siena—a Gothic cathedral wrapped in green and white marble stripes. -
3
Enjoy free time in Siena
After your guided tour wraps up, you'll have time to explore on your own. Grab an espresso at a café in the piazza, browse artisan shops tucked into ancient buildings, or simply wander the winding streets before lunch. -
4
Savor lunch and wine tasting at a Chianti vineyard
Next, your coach rolls through Chianti's vine-striped hills to a family-run organic winery. Sit down to a Tuscan feast of homemade pasta, prosciutto, aged cheeses, and cantucci cookies, all paired with estate wines like Chianti Classico and sweet Vin Santo. -
5
Wander through San Gimignano
From the winery, you'll head to San Gimignano, a hilltop town famous for its 14 surviving medieval towers that once served as status symbols for rival families. Stroll cobbled streets lined with workshops selling leather goods and ceramics, then climb one of the towers for views over Tuscany's patchwork countryside. -
6
See the Leaning Tower of Pisa
Your final stop brings you to Pisa, a coastal city known worldwide for one tilting marble tower. Walk across the green lawn of Piazza dei Miracoli to see the Leaning Tower, Cathedral, and Baptistery up close, then explore the historic center at your own pace before departure. -
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Your tour finishes in Florence
As evening approaches, you'll board your coach for the return trip to Florence. By the time you arrive back at Santa Maria Novella station, you've tasted Chianti wine, touched medieval stone, and crossed Tuscany from hill town to coast—all in one full day.
Additional Information
Discover what to expect, what’s included, and everything you need to know before booking.
Good to know:
Accessibility: Unfortunately, due to the uneven and steep surfaces, this day trip to Tuscany is not suitable for wheelchair users or those who may have trouble walking.
Dress Code: Knees and shoulders should be covered for entry into the Siena Duomo and Pisa Cathedral, as is required at most religious sites.
Dietary Restrictions: Vegetarian and gluten-free options are available, but please contact us in advance so we can work with our partners to accommodate your needs.
Alcohol Consumption: This experience includes sampling 4 wines; participants must be 18 or older to drink alcohol in Italy.
Tour Changes: At times the Duomo in Siena will be closed for religious services, in which case you will visit the Santa Maria della Scala Museum instead. The itinerary of this tour is subject to change based on weather, and traffic.
Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can enter sites on time.
Your 12-hour tour includes:
Expert English-speaking guide
Roundtrip transportation via air-conditioned coach from Florence
Guided walking tour of Siena with cathedral entrance
Tuscan lunch at a family-run vineyard
Sample 4 different wines
Free time in San Gimignano and Pisa
What to bring:
Comfortable walking shoes
Government-issued ID
Camera
Water
Scarf/shawl to cover knees and shoulders for religious sites
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Customer Reviews
All of the tours were excellent, especially Siena! Manolo and Marta were wonderful!
Our guide, Leah, expertly got us from location to location. She provided just the right amount of history and direction to let us know what to do while exploring on our own. The winery lunch was divine and we recommend ordering some for home. The bus also was first rate. One note, the walk from the meet up to the bus was a pretty long one. That's the only unexpected thing. A wonderful day in the care of a great group.
This was one of the highlights of our trip to Italy. It’s a long day, but it’s packed with incredible experiences and is an excellent way to see so much of Tuscany without worrying about any of the logistics. Our guide, Manolo, was outstanding. He was knowledgeable, friendly, funny, and kept the day running smoothly while sharing interesting history and local stories throughout the day. Siena was one of our favorite stops. It’s an incredibly beautiful and remarkably well-preserved medieval city that feels much more relaxed than Florence, Rome, or Venice. We also had an excellent local guide who taught us about the Palio and the traditions of the city’s contrade. It was especially exciting because her own contrada had just won the July Palio for the first time in over 20 years, and you could really feel her pride and passion as she brought Siena’s history to life. San Gimignano was another highlight. Seeing its famous towers from across the valley, it’s easy to understand why it’s often compared to a medieval Manhattan skyline. The town itself is small, beautifully preserved, and a wonderful place to wander the narrow streets, browse the shops, and simply soak in the atmosphere. The lunch at the Chianti winery exceeded our expectations. The setting was beautiful, the homemade food was delicious, and the wine was incredibly generous. Rather than just a few small tasting pours, bottles were brought to each table to enjoy throughout lunch, making it feel like a true Tuscan meal. At the start of the tour, the staff also asked everyone on the coach about dietary requirements. My wife is vegan, and they prepared a fantastic vegan meal for her without any hassle, which was a thoughtful touch. Climbing the Leaning Tower in Pisa was a unique experience and a perfect way to finish the day. We travelled well over 300 km throughout the day, but the comfortable, air-conditioned coach actually became one of the unexpected highlights. It was very hot during our visit, so each drive between destinations gave everyone a chance to cool off, relax, and recharge before exploring the next destination. We were travelling as a family with four boys, and everyone had a great time. Despite being a 12-hour tour, it never felt rushed, and there was a great balance of guided experiences and free time. If you’re looking for the best way to experience the highlights of Tuscany in a single day, we can’t recommend this tour enough. And if you’re lucky enough to have Manolo as your guide, you’re in for an unforgettable day.
Mano and Giuseppe we exceptional. Mano was amazing at explaining everything making us feel comfortable immediately! I hope to get another tour with him as the guide soon!
Frequently Asked Questions
What to bring?
Make sure to wear comfortable clothes appropriate to the season and a valid ID. During the summer, don’t forget a hat and a bottle of water!
What to bring?
Make sure to wear comfortable clothes appropriate to the season and a valid ID. During the summer, don’t forget a hat and a bottle of water!
Is this tour run by The Tour Guy?
This tour is operated by one of our trusted and vetted partners in Florence.
What if I have concerns about my mobility on this tour?
Unfortunately, due to the uneven and steep surfaces in the locations we will be visiting, this day trip to Tuscany is not suitable for wheelchair users or those who may have trouble walking.
What happens if it rains?
We run our Tuscany day trips rain or shine. In the case of extreme weather conditions, cancellations may occur, and a full refund will be provided.
Is there any chance my tour might be canceled?
On the rare occasion the tour is canceled, we'll inform you as soon as possible. We will work with you to reschedule your tour when possible or provide a full refund.
Is there a dress code to enter the religious sites on this tour?
Both men and women are required to cover their knees and shoulders, otherwise, the Cathedral in Siena may refuse entry and you’ll miss out on a portion of your tour. We understand the summers in Tuscany can be hot, so a great alternative is to bring a shawl/scarf/sweater with you. That way you can cover your knees and shoulders when necessary.
How comprehensive is this tour of Tuscany?
In the spirit of seeing as much of Tuscany in one day as possible, the time spent in Siena, San Gimignano and Pisa are abbreviated compared to our private tours to each of these areas. You'll still get to experience all the most important elements of these impressive towns and cities.
Does the Duomo in Siena ever experience sudden closures?
Yes, at times the Duomo in Siena will be closed for religious services. If this is the case during your tour, you will visit the beautiful Santa Maria della Scala Museum instead.
Are tickets to the Leaning Tower of Pisa included?
Tickets to the Leaning Tower of Pisa are not included in the price paid. In case you wish to add them, please let us know and we will do our best to secure them for you.
Is lunch included in the price of the tour?
Yes, a delicious Tuscan lunch at the wine estate is included!
What if I have food allergies, intolerances, or other dietary requirements?
Not a problem at all, vegetarian and gluten-free options will be available. Please contact us in advance so we can do our best to accommodate your needs. We will work with our tour partners to provide you with an alternative when possible.
How many glasses of wine will I get?
You'll enjoy at least 4 different wine varieties during your wine tasting. In addition to your tasting, wine will also be served with lunch.
What if I don’t drink alcohol but I’d still like to join a food tour?
Not a problem. Please let us know in the comment box when you book your tour so we can make sure an alternative drink is provided.
Can I bring my kids and do I have to pay for them?
Kids are welcome on this tour, and children aged 8-17 pay a reduced fee. Children 7 and under may join for free. Please choose accordingly during the booking.
Does this tour include hotel pickup?
No hotel pickup is included on this tour. You’ll meet your guide at the designated meeting point, conveniently located in Piazza Stazione.
