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(4,815)
Host at the vineyard promised lots of wine. That didn’t happen. The food that accompanied it was quite poor. The Siena cathedral guide was repetitive I stopped listening and did my own thing. The guide for the day Riccardo was great!
Good experience to have .many things covered
Thank you for your review! We’re glad you enjoyed the variety of the day and the chance to experience so much of Tuscany in one trip. We hope you took home many good memories from the places visited.
Ricardo was an excellent tour guide. He was very knowledgeable and friendly! Would book this again!
Great day, very organized & informational. Thank you Fabi, Luisa & Ellis. Be prepared for lots of walking (some hilly areas). Wonderful opportunity to meet & chat with others on tour at lunch in group seating.
Dear Pat, Thank you for your thoughtful review! We’re glad Fabi, Luisa, and Ellis made the day enjoyable and easy to follow. The shared lunch is also a lovely chance to connect with fellow travelers along the way. And your tip about comfortable shoes is certainly a useful one! Warm greetings from Tuscany.
Our guide Freddy was very good and knowledgable. Excellent day trip, every part of it was great. From the wine tasting to the exploration of the historic sites throughout the Tuscan countryside.
A fantastic day in Tuscany from start to finish! It’s great to hear that Freddy’s knowledge added so much to the experience and that you enjoyed every part of the itinerary, from the wine tasting to discovering the region’s historic gems. Thank you for joining us, and warm greetings from Florence!
I felt missing more historical information about the places visited
Muito obrigado pela sua avaliação e pelo seu comentário. Ficamos felizes que tenha aproveitado a experiência e agradecemos a sua sugestão sobre incluir mais informações históricas durante as visitas. O seu feedback é muito importante para nós. Esperamos recebê-lo novamente em uma próxima experiência na Toscana!
Lovely day. Big day - wear comfy clothes & shoes, more walks than expected but so beautiful! Loved the wine tasting & lunch, towns visited were peaceful & stunning. We loved your guide Fred.
Dear Hannah, Thank you so much for your lovely review! We’re delighted that you enjoyed the beautiful towns, the wine tasting and lunch, and the whole experience with Fred. It is certainly a full day, so comfortable shoes are a great tip! We hope to welcome you back for another wonderful adventure in Tuscany. Warm greetings from Florence!
Fred did a fantastic job of being informative yet short and to the point. He was very knowledgeable about the places we went and made it easy to find him again once we left the places. Great day out
Thank you for your wonderful review! We’re delighted that Fred’s clear explanations, knowledge, and organisation helped make your day so enjoyable. It’s great to hear that everything felt easy and well managed throughout the trip. We hope to welcome you back for another memorable experience soon!
Great tour today with Federico! Good pace of the visits. Each of the stops was interesting. We really enjoyed it!
Merci beaucoup Patrice pour votre enthousiasme ! Nous sommes ravis que vous ayez apprécié le rythme de la journée, les différentes étapes du programme et l’accompagnement de Federico. Votre satisfaction nous fait très plaisir. Au plaisir de vous accueillir à nouveau pour une prochaine découverte de la Toscane !
Very good guide, Fred is very pleasant and very clear. Very nice program
Merci beaucoup pour votre très beau retour ! Nous sommes ravis que vous ayez apprécié le programme ainsi que la gentillesse et la clarté de Fred. Ce sera un grand plaisir de vous accueillir à nouveau pour une prochaine expérience en Toscane. Bien chaleureusement de Florence !
