4.9(23 reviews)
Private Siena San Gimignano Tour with Winery Lunch
From€500
8 hours
Florence, Italy
About this activity
Experience the charm of Tuscany on a private tour from Florence, visiting Siena and San Gimignano, and savoring a traditional winery lunch.
Highlights
- Explore Siena's historic center
- Visit the iconic San Gimignano towers
- Enjoy a traditional Tuscan lunch at a local winery
- Discover the rich history of Tuscany's medieval towns
- Experience personalized service with a private guide
Full description
Discover the enchanting Tuscan countryside on a private tour from Florence. Begin with a guided exploration of Siena's historic center, renowned for its medieval architecture and the famous Piazza del Campo. Then, visit San Gimignano, known as the 'Town of Fine Towers,' where you'll wander through narrow streets lined with medieval towers and enjoy panoramic views of the surrounding vineyards. The tour includes a delightful winery lunch, featuring local Tuscan specialties paired with exquisite wines. This personalized experience offers a deep dive into Tuscany's rich history and culinary delights, all in the comfort of a private vehicle and with the expertise of a knowledgeable guide.
Included / Excluded
- Private transportation from Florence
- Guided tours of Siena and San Gimignano
- Winery lunch with local Tuscan specialties
- Gratuities for the guide and driver
Itinerary
1
After meeting your expert guide, an air-conditioned minivan will whisk you away to the first stop of the day, Siena. The drive to Siena will take about 1 hour and 15 minutes.. During the journey, your guide will explain the itinerary for the day and entertain you with interesting facts about Siena and Tuscany!!!
Duration: 15 minAdmission: NOT_APPLICABLE
2
After lunch, a 45-minute drive will take you to Siena, 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
3
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
4
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'. You will visit a church and museum of one contrada. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. 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
5
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
6
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!
Duration: 15 minAdmission: YES
7
After the morning exploration of Siena, a 15-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Visit the farm, 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 meet fellow travelers while feasting on 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: 2 hoursAdmission: YES
8
San Gimignano is a small, walled Tuscan hill town 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: 2 hoursAdmission: NOT_APPLICABLE
9
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
10
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
11
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: 30 minAdmission: NOT_APPLICABLE
12
After the visit of San Gimignano, a 1-hour drive will take you back to Florence. You will dropped off at the start point with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.
Duration: 15 minAdmission: NOT_APPLICABLE
Important information
Know before you book
- The tour is conducted in English; please inform the operator of any language preferences in advance.
- Children under 18 must be accompanied by an adult and may not participate in wine tasting.
- The tour operates rain or shine; dress appropriately for the weather conditions.
Know before you go
- Wear comfortable walking shoes suitable for cobblestone streets.
- Bring a camera to capture the picturesque landscapes and historic sites.
- Ensure you have a valid ID for wine tasting participation.
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
Good to know
- Disclaimer: Only 18 years old and above are allowed for wine tasting
Traveler reviews
4.923 reviews
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Incredible tour!!!
We loved all the places we visited!! Our tour guide Mano was the best!!! A very recommended tour if you are in Florence. The bus was very comfortable and our driver very good. All the places we visited were lovely!!! San Gimaniano is incredible!!! Pisa was perfect!!! And Siena OMG what a City!!! Perfect way to see them all!!!
CLandaVApr 29, 2026TRIPADVISOR
So much fun and educational!!!
Luca was amazing! We learned so much history and had fun exploring Sienna, San Gimignano and Pisa! Would definitely recommend for a day trip :)
jasminz212Oct 30, 2025TRIPADVISOR
Excelente servicio de Emma y Guiseppe!!
El tour fue excelente! Emma, our guide, very nice, with very good explanations and excellent recommendations throught the tour. And Giuseppe … la creme de la creme !!
laurafM306LHJun 10, 2025TRIPADVISOR
A Tuscany Excursion To Remember!
Walkabout Tours is the best! I had a custom tour for my high school group which included teachers and students. What a wonderful experience! We started in the beautiful town of San Gimignano, stopped for a superb lunch at a nearby winery and then continued on to Siena. The group had an amazing time! Our guide for the day was Manolo and he was top notch! He was full of historical facts. He was fun, very considerate, had a good sense of humor and he was very professional. Everyone enjoyed his presentation. Everything ran perfectly on schedule and Manolo managed the tour schedule well. He was very conscientious of every detail and he went well above and beyond our expectations! The entire day was a wonderful experience--one our group will never forget!
debbierK5640YVApr 13, 2025TRIPADVISOR
Romantic Tuscany day trip for two!
Our guides Alex and Eliana were outstanding! The whole day was a wonderfully romantic and informative experience. The perfect balance of history, guided tour, and on our own time. The winery was gorgeous, the tasting more than generous, and the food was excellent. I would highly recommend this tour to anyone who wants to experience the Tuscany countryside, learn some history, and have lunch at an amazing winery with some of the best wine made!
Michelle DMar 31, 2025TRIPADVISOR
Additional information
Disclaimer: Only 18 years old and above are allowed for wine tasting