San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch
Description
Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence. Please note that the order of the visits may change (*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Tour Options
Itinerary
Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from Florence.
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.
Step inside a storybook fortress village encircled by intact walls and ramparts, beloved by filmmakers and history fans alike. Enjoy free time to browse tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Join a guided walking tour (if option selected) through contrade banners, artisan storefronts, and grand palazzi that reveal Siena’s golden age. Afterward, enjoy free time to sip an espresso, browse boutiques, or continue exploring this Gothic masterpiece at your own pace.
Piazza del Campo is the main square of Siena, famous for its distinctive shell shape and elegant brick pavement. Surrounded by historic buildings, it is home to the Palazzo Pubblico and the Torre del Mangia. It is also the setting for the famous Palio di Siena, a historic horse race between the city’s districts.
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.
Highlights
What's included
Traveller Ratings
Important Information
- 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
- A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.
- 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.
- Comfortable walking shoes are recommended.
- From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
- It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay or no show 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.
- Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
- Vegetarian and gluten-intolerant options are available at the wineries; however, cross-contamination cannot be fully excluded.
- 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.
Reviews(4,992)
The tour was great fun despite for our family of four, and it wasn’t too strenuous for our 10 and 12-year-old daughters. San Giminiano and Sienna were magnificent and well worth the trip. We took the cathedral tour in Sienna and that was also very much worth the time. Martha, our tour guide, was absolutely delightful all day long, and we got so much more out of the trip with her commentary. The lunch and wine tasting far exceeded our expectations, too. Just a great day start to finish, and one I’d highly recommend.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you for such a wonderful and detailed review! We’re thrilled that your whole family, including your 10 and 12 year old daughters, enjoyed discovering San Gimignano and Siena at such a comfortable pace. It’s fantastic to hear that Marta’s commentary brought the history to life and that the cathedral visit, lunch and wine tasting exceeded your expectations. We hope this becomes one of those special family memories you’ll treasure for years to come! Warmest regards from Tuscany, Caf Tour & Travel
Martha our guide was incredible ! She explained us everything very clearly , the tour is very well organized everything on time , we did so much things in just 1 day . I loved the lunch experience in Toscana wow with the food and wine 100/10 .. important to mention that the bus was super comfortable for doing the tour , our family loved this experience ❤️
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for your fantastic review! We’re thrilled that Marta made your day so enjoyable with her clear explanations and that you were able to experience so much of Tuscany in a single day. Hearing that the lunch and wine tasting reached a “100/10” truly makes us smile! We’re also delighted that your family appreciated the comfortable journey and smooth organization. We hope to welcome you back for another unforgettable Italian adventure! A big Tuscan thank you, Caf Tour & Travel
Awesome tour with Martha, our guide!
Good Morning from Caf Tour & Travel, Dear Customer, Thank you very much for your kind review! We’re delighted to hear that you had such a great time exploring Tuscany with Marta. With its medieval towns, rolling hills and unforgettable landscapes, this region offers something special at every stop, and we’re happy Martha helped make your experience even more enjoyable. We hope to see you again soon for another beautiful journey through Italy! Warm regards from Tuscany, Caf Tour & Travel
Marta was a great guide! Very polite and kind, and Ellis is a very good driver.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you very much for your lovely review! We’re so pleased to hear that Marta was a kind and polite guide and that Ellis helped make your journey smooth and comfortable. It’s wonderful to know you enjoyed discovering San Gimignano, one of Tuscany’s most enchanting medieval towns. We hope to have the pleasure of welcoming you back to explore even more of our beautiful region! Warm wishes and arrivederci from Italy, Caf Tour & Travel
Marta was a fantastic guide and the tour covered a LOT of amazing places. Would highly recommend!
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for your wonderful feedback! We’re delighted that Marta made your experience so enjoyable and that you appreciated how much of Tuscany you could discover in one day. From the medieval charm of San Gimignano to the beauty of Siena and the Chianti countryside, every stop offers a different glimpse into the heart of Tuscany. We hope to welcome you back soon for another memorable Italian adventure! With our warmest regards, Caf Tour & Travel
We had an amazing tour through Tuscany!🍷🇮🇹 We visited beautiful medival towns, and enjoyed a wonderful wine tasting along the way. Aaron was our tour guide, he was fantastic , fun and friendly along with him Danielle(our excellent driver).
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for your wonderful review! We’re thrilled that you had such an amazing day discovering Tuscany’s beautiful medieval towns and enjoying the wine tasting along the way. Aaron’s fun and friendly personality, together with Danielle’s excellent driving, clearly helped make the journey even more enjoyable. We hope to welcome you back soon for another taste of the Tuscan lifestyle! Cheers from Tuscany, Caf Tour & Travel
Aaron was the guide and Daniele was the bus driver. Aaron explained everything twice, in english and Spanish. Very nice and quite funny guy. The lunch was good and had gluten free pasta for those who asked. Very tasty wines. Nice trip overall
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for your fantastic feedback! We’re delighted that Aaron’s explanations in both English and Spanish made the history and stories of Tuscany easy and enjoyable to follow. We’re also pleased that you enjoyed the lunch, including the gluten-free option, and the delicious local wines. We hope to welcome you back soon to discover even more of Italy! A warm “a presto” from Tuscany, Caf Tour & Travel
Was a sensational day with Aaron and Danielle. Aaron was excellent, so knowledgable and super friendly. Can highly recommend Aaron. Thank you for such a memorable day.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you for such a wonderful review! We’re thrilled that you had a sensational day with Aaron and Danielle and that Aaron’s knowledge, friendliness and enthusiasm made such a strong impression. It’s fantastic to know that the experience became such a memorable part of your trip to Tuscany. We’ll be delighted to share your kind words with them, and we hope to see you again in Italy! Warmest Tuscan regards, Caf Tour & Travel
Had a really good time. Our guide Aaron was friendly, funny, and attentive. Great experience overall and would recommend!
Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for your wonderful review! We’re thrilled that you had such a great time exploring Tuscany and that Aaron’s friendliness, humor and attentiveness made your day even more enjoyable. A little laughter and good company can make a long day of sightseeing truly memorable! We truly appreciate your recommendation and hope to welcome you back again soon. A warm “a presto” from Tuscany, Caf Tour & Travel
Lovely tour of Siena and the medieval towns. Siena's Duomo is magnificent. And nothing beats tasting Tuscan wines in their vineyard. Special thanks to Ricardo and Nino for taking good care of us.
Good Morning from Caf Tour & Travel, Dear Customer, Thank you for your wonderful review! We’re thrilled that you enjoyed exploring Siena and its beautiful medieval towns, and we couldn’t agree more about the magnificence of Siena’s Duomo. There is something truly special about tasting Tuscan wines right where they are produced, surrounded by the vineyards. A special thank you from us to you for recognizing Riccardo and Nino, we’ll be delighted to share your kind words with them! A warm Tuscan “a presto”, Caf Tour & Travel
