5.0(15 reviews)
Private Tuscany Tour: Pisa, Siena, San Gimignano & Winery Lunch
From€580
8 hours
Florence, Italy
About this activity
Discover Tuscany's iconic cities—Pisa, Siena, and San Gimignano—on a private tour from Florence, complete with a traditional winery lunch.
Highlights
- Marvel at Pisa's Leaning Tower
- Explore Siena's historic city center
- Wander through San Gimignano's medieval streets
- Enjoy a traditional Tuscan lunch at a winery
- Experience the scenic Tuscan countryside
Full description
Experience the charm of Tuscany on a private tour that takes you from Florence to the iconic cities of Pisa, Siena, and San Gimignano. Begin your day marveling at Pisa's Leaning Tower and the historic Piazza dei Miracoli. In Siena, wander through its medieval streets and visit the stunning Siena Cathedral. Then, explore San Gimignano, known for its well-preserved medieval architecture and towers. Throughout the day, enjoy a traditional Tuscan lunch at a local winery, savoring regional specialties and wines. This tour offers a personalized and immersive experience of Tuscany's rich history and culture.
Included / Excluded
- Private transportation from Florence
- Guided tours of Pisa, Siena, and San Gimignano
- Traditional Tuscan lunch at a local winery
- Gratuities for the guide and driver
Itinerary
1
Siena is a real medieval gem and in fact one of Tuscany's most famous and beautiful hill top towns. When you arrive you will join a 1 hour guided walking tour with a local city guide through Siena's most beautiful streets and sites, including the entrance to the Cathedral, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.
Duration: 3 hoursAdmission: NOT_APPLICABLE
2
The first stop on the walking tour of Siena is a bank that has its headquarters in this square - the oldest surviving bank in the world. It's called Monte dei Paschi di Siena and it has been running continuously since 1472. Your guide will explain how Siena's wealth through the centuries came from being on the pilgrim route known as the Via Francigena, a route that led pilgrims between Rome and Northern Europe. Siena prospered as a banking town by lending money and exchanging money for the merchants who were using the pilgrim route as a safe travel route. The Sienese are still wealthy from their banking past and are still famous for their banks today!
Duration: 15 minAdmission: NOT_APPLICABLE
3
Your local guide will then walk through some of the most picturesque back streets of Siena, while telling about something very unique to Siena are the 17 districts which make up the historical centre.The name for these ancient divisions is 'contrade'. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. You will visit the church and museum of one of the contrade. The sense of identity and belonging to ones 'contrada' is extremely important. They are self-contained little worlds with their own church, where newborns are baptised, and a public fountain where the newborns are baptised a second time! Needless to say there are strong rivalries between these districts, that explodes during the Palio horserace held twice a year in Piazza del Campo.
Duration: 15 minAdmission: NOT_APPLICABLE
4
Piazza del Campo is one of the most beautiful squares you will ever see and it is also the city's gathering place, where the locals meet for a coffee and to chat and of course gossip. The unusual square (actually not a square, it's in the shape of a sea-shell, and sloping!) is the site of the famous Palio horse-race. A 600 year old tradition of Siena. The piazza gets transformed into a racing track twice a year and the contrade, or neighbourhoods of the city battle out for the highest honour possible – winning the palio. You'll hear more about this on the tour, your local guide will set the scene so that you can somehow live for a moment the vibrant atmosphere of this incredible race.
Duration: 15 minAdmission: NOT_APPLICABLE
5
Our walking tour then ends inside the Duomo of Siena – undoubtedly the jewel of the city. If you've seen the interior of Florence's Duomo, it is nowhere near as spectacular as Siena's. The most unique part of this city's cathedral is its floor. It's an artwork on its own, made out of the world's most precious marbles – in fact, it's a combined masterpiece of over 50 images created over 2 centuries by some of Italy's most important artists. Then, enjoy walking through the city center on your own before meeting your guide again to head to your next stop!
Duration: 15 minAdmission: YES
6
After the morning exploration of Siena, a 45-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Enjoy an informal wine tasting lesson and a traditional Tuscan lunch with plenty of wine, in the most gorgeous location overlooking stunning views of the surrounding countryside. Take the opportunity to try fresh organic farm food of homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad, and Tuscan biscotti. There is also the opportunity to buy the local products of the winery before heading to San Gimignano.
Duration: 1h 30mAdmission: NOT_APPLICABLE
7
After lunch, a 15-minute drive will take you to San Gimignano, that is an even smaller, walled Tuscan hill town than Siena - about 6 times smaller - and a UNESCO World Heritage Site. San Gimignano is most famous for its towers of which there were 72 though there are just 14 remaining today. From this the city gets its nickname of the little Manhattan of Tuscany. Your guide will give you a map and point out the best landmarks, so that you can roam independently the picturesque streets and squares of this enchanting hilltop town.
Duration: 1h 30mAdmission: NOT_APPLICABLE
8
Your guide will lead you to the entrance city gate and that is where the main boulevard starts from, Via San Giovanni. This street will take you to Piazza della Cisterna, the heart of San Gimignano and also the setting for several films. This was the square where festivals and tournaments took place while the Piazza Duomo was the religious and political centre. This is also where the best gelato in the world is – Gelateria della Piazza 'Dondoli'. It's won many awards as the best gelato, you could try it and see what you'll think!
Duration: 20 minAdmission: NOT_APPLICABLE
9
From Piazza della Cisterna, the next piazza along is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but is well worth visiting! The beautiful interior of the cathedral walls is filled with colorful 14th century frescoes in every space available. You could also climb up one of the medieval towers here in this piazza, next to the Duomo (the Torre Grossa) to appreciate the incredible 'BIRD'S EYE' view over San Gimignano.
Duration: 20 minAdmission: NOT_APPLICABLE
10
Another stunning view over the towers of San Gimignano is from La Rocca. It is easily accessible behind the Duomo and It is a peaceful setting with olive trees and the wall surrounding the garden that formed part of the 14th-century fortress Medici of Florence built to protect this town from Siena. if you walk to the back of the garden and climb the steps to the top, the views over San Gimignano's skyline are absolutely breathtaking.
Duration: 20 minAdmission: NOT_APPLICABLE
11
After the visit of San Gimignano, a 1 hour and an half scenic drive through iconic Tuscan countryside will take you to your final stop, Pisa.
Duration: 1 hourAdmission: NOT_APPLICABLE
12
Upon arrival, your guide will lead you straight to the famous Square of Miracles. At first sight, it is truly breathtaking - the white marble buildings glow in contrast to the perfect, green lawns. You will have about an hour to explore the Cathedral, Baptistry, Monumental Cemetery, and of course - The Leaning Tower!
Duration: 15 minAdmission: NOT_APPLICABLE
13
During your time in Pisa, you can climb the Leaning Tower to admire the incredible views of the Square of Miracles from above. The views from the top of the Tower are truly breathtaking - from the monuments below, to the city surrounding the square, the Arno River, and the countryside in the distance... and part of the fun is also climbing the stairs inside the Leaning Tower that we will make you feel a bit dizzy at the end!
Duration: 30 minAdmission: YES
14
After leaving Pisa, it will take about an hour to return to Florence. You will dropped off at the start point with a camera full of pictures and a stomach full of hearty Tuscan food.
Duration: 1 hourAdmission: NOT_APPLICABLE
Important information
Know before you book
- This is a private tour; the vehicle and guide are exclusive to your group.
- The tour operates rain or shine; cancellations due to weather are rare.
- Please inform the operator of any dietary restrictions in advance.
Know before you go
- Wear comfortable walking shoes for cobblestone streets.
- Bring a camera to capture the picturesque landscapes.
- 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
Traveler reviews
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Fun tour guide and very fun experience
leaning tower of pisa was awsome. great time david was a great tour guide!!
FarAway17832543498Jan 25, 2026TRIPADVISOR
A Fun-Filled Memorable Day Visiting 3 Italian Cities and a Winery
Manolo was a fantastic tour guide and Ali an excellent driver for our day long trip from Florence to Siena, Vecchio Maneggio Agriturismo, San Gimignano and Pisa. Mano is absolutely great at what he does!
Y6133RTmelissabOct 22, 2025TRIPADVISOR
We had an amazing day...
We had an amazing day with Alessandro today as our private tour guide. We learned so much about Italy’s history and saw the most beautiful cathedrals. The farm with wine tasting was a highlight and they are able to accommodate for dietary restrictions if needed. So far this was our favorite day in Italy! I would definitely recommend this tour!
Sarah_MOct 11, 2025VIATOR
Fantastic Journey through Tuscany
What an absolute fabulous tour. Gabriel was an excellent guide and how Labi got the bus through all those tiny roads is beyond me! The farm house lunch alone would have made the trip worthwhile but adding Siena, San G and Pisa was icing on the cake.
kimkP6759MNJul 13, 2025TRIPADVISOR
Amazing Day Tour
We had an amazing day tour traveling to these three cities, it was planned out perfectly. Antonio (toni) was a perfect tour guide for our family, very knowledgeable but also very good personality. Flexible to our needs. We had a great local guide in Siena that highlighted the city, had the Worlds Best Gelato in San Gimignano, and our lunch at a Tuscan winery included our favorite pasta dish of our trip, the bolognese. Pisa was planned as a short stop to see the Tower, and that really is enough time and all you need to see here. I would give this more than 5 stars if I could, highly recommend.
151pateJul 3, 2025TRIPADVISOR