• San Gimignano - Explore the UNESCO-recognized “town of towers,” a beautifully preserved medieval hilltop treasure offering panoramic views, artisan shops, and picturesque alleys. Enjoy plenty of free time for personal exploration, from savoring award-winning gelato to capturing skyline photos—perfect for a day trip from Florence.
• Piazza della Cisterna - The charming center of San Gimignano, surrounded by tower-houses and featuring a medieval stone well that anchors the square. A brief, curated stop for photos and storytelling that brings the town’s merchant history to life.
• Mura di San Gimignano - Glide past the 14th-century fortifications and the most iconic gate, imagining pilgrims and traders entering centuries ago. Your tour leader provides context and highlights to help you appreciate the engineering and defense of a Tuscan walled city.
• Monteriggioni - Enter a storybook fortress village encircled by intact walls and ramparts, cherished by filmmakers and history enthusiasts alike. Enjoy free time to explore tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany.

(*) From November to March, the itinerary excludes the stop at Monteriggioni and the return to Florence is approximately 30 minutes earlier.

• Chianti Road - 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.
• Siena - 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 Salimbeni - Admire refined Renaissance architecture and learn 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.
• Piazza 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.
• Duomo 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.
• Biblioteca Piccolomini - 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)
• Via Chiantigiana - 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.

• Licensed Tour Escort for on-board insights and coordination
• Round-trip transport by comfortable, air-conditioned coach from Florence
• Assistance by Caf Tour Team at the meeting point
• Chianti winery experience: guided cellar & vineyard visit plus 3-course Tuscan lunch
• Wine tasting: three Chianti wines plus traditional vin santo
• If option selected: Guided walking tour of Siena with a professional local guide
• If option selected: Skip-the-line access to visit inside Siena Cathedral & Piccolomini Library
• If option selected: from November to March the visit in Siena can be bilingual (English and Spanish)
• If option selected: April to October, visit in Siena is monolingual. Language selected while booking

• Our Shared Round Transport option does NOT include: Siena Guided Visit, Cathedral admission
• From November to March, the itinerary does not include the stop at Monteriggioni
• Hotel Pick-Up and Drop-Off is not available

Experience the beauty of Tuscany in a single day starting from Florence. Begin your journey in the hilltop UNESCO town of San Gimignano, where you’ll have approximately 2 hours to explore its towers, charming lanes, and artisan shops. Next, visit Monteriggioni (seasonal; see note), a beautifully preserved walled village, with time to explore within its walls. Travel through the picturesque Chianti hills to a welcoming winery for a tasting of three wines and a delightful three-course farm-to-table lunch, concluding with cantucci. In the afternoon, enjoy a guided walking tour of Siena: wander through Piazza del Campo, view the Palazzo Pubblico, and admire the Cathedral (interior visit if option selected). Conclude with some free time before heading back to Florence.

Please note that the sequence of visits may vary.

(*) From November to March, the tour does not include a stop at Monteriggioni, and the return to Florence is approximately 30 minutes earlier.

• 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.

For a full refund, cancel at least 24 hours before the scheduled departure time.