Unveil Tuscany's Medieval Heart: Siena, San Gimignano & More
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.
Reviews
Reviews and Rating (Tripadvisor)
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Reviews by Tripadvisor travelers
Don D, 12/8/2025 2:11:30 PM
Wonderful tour, very laid back approach, just pay attention to the time and be back to the bus when you are told to. The English guide in Sienna was very good, a little quick but thorough and very knowledgeable. I don't recommend the lunch option. Being from the midwest in the US, it was like having grandma's hot dish. However, if you do the lunch, you are already at the meeting stop to get back to the bus. And if you're an assassin's creed fan, you can walk some of the same streets as Ezio.
Explore46479529085, 12/8/2025 12:43:48 PM
Great experience , Sara , Alex and Boris were all very accommodating, fun, and professional! I would highly recommend booking with this team
Denise F, 12/8/2025 12:43:28 PM
It was a well organized and informative tour at some of the most beautiful towns in Italy! Sara and Alex made us feel comfortable and well cared for anticipating our needs. We didn’t feel rushed and fully enjoyed every stop. Highly recommend as a great way to spend a fun day in Tuscany!
Escape02596345881, 12/3/2025 12:30:48 PM
Great time on the tour to San Gimignano, Siena and Chianti. Had a wonderful guide Giancarlo who was nice and knowledgeable. Nice not to worry about driving or taking other form of transport to these places. The wine tasting was good and a beautiful winery. Thank you CiaoFlorence also great affordable price!
Fred_H, 12/2/2025 10:53:31 PM
Nice Tuscany day tour. Alex was great in explaining about the various areas we visited, and the driver Cozimo did a good job getting us back safe.
I7245UIkevina, 11/26/2025 1:43:53 PM
Very enjoyable day and tour. John was a wonderful guide and very helpful. The sights and scenery of Tuscany were fantastic.
Climber41471462980, 11/25/2025 12:55:21 PM
John was the BEST!!!!! Book your tour with him!!!!! He was incredibly knowledgable and very kind. He answered every question before I even needed to ask it. He clearly knows what he's doing!
Kelli_W, 11/24/2025 4:32:27 AM
Ronaldo and Roberto did a great job of getting us to our destinations and communicating things to do at each stop. This tour is a large group tour on a coach bus. We still kept to our schedule. Siena is beautiful along with the other stops. The only thing i wish were different was the order of the stops. It was close to dark when we arrived to San Gimignano and would have preferred to be in Siena in the evening. Thanks for conducting the tour, so we could see more on our Italy trip!
mattoZ5397AJ, 11/23/2025 12:40:47 PM
Truly an unforgettable experience full of fun, culture, good company and good wine. The entire tour was incredibly smooth and coordinated which removed so much stress from attempting to plan it. From our amazing tour guide, Roberto, to our smooth and efficient driver, Renaldo, they took care of us completely and ensured we had a perfect experience. I will recommend Caio Florence to all my friends and family!
Paul_H, 11/19/2025 4:11:16 AM
Beautiful countryside and interesting places to see. The reason rating not higher was it combined 3 languages on same tour Made it complicated. Winery was a commercial operation. Hoped the wine tasting to be overlooking the Tuscan hills
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Specialized infant seats are available
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- May be operated by a multi-lingual guide
- Please note that the given order of the visits may change
- Kindly note that the Semi independent option does not include the professional guide in Siena
- LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
- HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
Departure point
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!Return details
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.Redemption
• A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements • Comfortable walking shoes are recommended • The given order of the visits may change • Please show up 20 minutes before the tour departure Times are subject to change due to local traffic conditions.24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund