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Offered languages
- English
- Spanish
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 & vin santo. 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
What's Included
Meeting and pickup
Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.
Itinerary
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1San Gimignano
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.
2 hours • Admission ticket free -
2Piazza Della Cisterna
The atmospheric heart of San Gimignano, framed by tower-houses and a medieval stone well that anchors the square. A short, curated stop for photos and storytelling that brings the town’s merchant past to life.
10 minutes • Admission ticket free -
(Pass by)
Glide past the 14th-century fortifications and the most iconic gate, imagining pilgrims and traders entering centuries ago. Your tour leader shares context and highlights so you can appreciate the engineering and defense of a Tuscan walled city.
Admission ticket free -
3Monteriggioni
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
40 minutes • Admission ticket free -
4Strada Statale 222 Chiantigiana
Travel the legendary wine route through rolling vineyards, stone farmhouses, and cypress-lined ridges—classic Tuscany in every direction. Stop at a welcoming Chianti winery for a tasting of three wines and a farm-to-table 3-course lunch, ending sweetly with cantucci e vin santo.
1 hour 30 minutes • Admission ticket included -
5Siena
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.
2 hours 30 minutes • Admission ticket free -
6Piazza Salimbeni
Admire refined Renaissance architecture and hear how the world’s oldest operating bank shaped Siena’s wealth and culture. It’s a concise stop with rich history and elegant façades perfect for quick photos.
15 minutes • Admission ticket free -
7Piazza del Campo
Stand in Siena’s shell-shaped stage, home to the legendary Palio horse race, and take in Palazzo Pubblico and Torre del Mangia. Your guide unpacks centuries of tradition so the square’s drama and design truly resonate.
15 minutes • Admission ticket free -
8Duomo di Siena
Gaze at the striped marble exterior, a Gothic marvel that crowns the city; (if option selected) interior visit to admire polychrome floors and masterpieces. A powerful highlight that pairs art history with unforgettable visuals.
15 minutes • Admission ticket included -
9
Step into a jewel box of vivid Pinturicchio frescoes and illuminated manuscripts that glow with Renaissance color. A quick but dazzling stop that rewards art lovers and casual visitors alike. (if cathedral option selected)
10 minutes • Admission ticket not included -
(Pass by)
Return along vineyard-draped hills and ancient hamlets, the perfect finale for golden-hour photos across the Tuscan countryside. A smooth, scenic drive back to Florence rounding off a day of towers, wine, and medieval splendor.
Admission ticket free
Additional info
- 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.
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Additional info
- 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.
- 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.
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Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Rating
You can cancel up to 24 hours in advance of the experience for a full refund.
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