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)
5 stars
4 stars
Reviews by Tripadvisor travelers
cathy t, 10/21/2025 4:49:56 AM
Wonderful day trip from Florence. Sienna is a beautiful walled city like no other. The Cathedral is magnificent. Walk and enjoy the quaint shops and restaurants! We had pasta in a restaurant just down the way from Cathedral and it was wonderful. Wine tasting was fun and informative- oil oil and balsamic vinegar was wonderful. The last stop in have a gelato and take in the beauty of medieval times. Beautiful shops !
CatsRSoft, 10/21/2025 4:30:48 AM
Roberto, Scirin and Luca were very nice and experts. Everything was wonderful and memorable. It’s one of my best decision to join the tour. The Sienese guide, Laura, was very informative, too! If you have a free day while staying in Florence. This tour is totally recommended. Do not miss!
Randall_B, 10/21/2025 4:11:38 AM
Kiara and Tatiana were wonderful tour guides. They provided clear direction and were very friendly. The different town was very interesting and the wine tasting was a lot of fun.
nicksF9860SZ, 10/21/2025 3:21:58 AM
A wonderful tour led by fantastic hosts Martina, Titania (sorry not sure of spelling?) and the driver Mario. Meeting point was clearly explained, busy with lots of people but well organised check in. A suggestion for the directions is that you can easily get there via the train station Firenze Santa's Maria Novella, by walking down the platform (#18) and down the ramp. Siena and San Gimignano are fab, Sienna cathedral/Duomo is a must see at €5 entrance even if you don't particularly like churches. San Gimignano is a stunning medieval town, barely changed in 500+ years. Monteriggioni is delightful, a tiny village on top of a hill within its own walls, a great place for a 30 min walk & coffee in the small and sunny piazza. Siena local guide Elena was full of interesting facts and stories about the city. Wine tasting was fun but not sure we'd do it again. Highly Recommended !
Wander485873, 10/20/2025 3:38:13 PM
Three cities of Chianti. Medieval structures, beautiful scenery… must come back for more. Poggio Ai Laghi winery tasting was fabulous ordered for home!!! Guided were pleasant, lovely and informative kept a large group organized and attended to.
ZenGus, 10/20/2025 2:59:58 PM
What an incredible trip! The guides were knowledgable they switched fluently from one language to the other. They made all the history exciting and interesting. They facilitated movement from city to city with ease. I really enjoyed the day. It went so quickly.
Elizabeth_M, 10/20/2025 12:48:59 PM
Got an overview from hosts on tour but be prepared to use limited time wisely. So much to see so little time. Group of 70 was managed well
Evan_F, 10/20/2025 8:11:22 AM
The towns of Monteriggione, Sienna and San Gimignano were a delight. Even though our tour was all day, the time spent was insufficient at Sienna and San Gimignano. These were lovely towns and a lot to experience but a few hours does not do justice! If you are looking for a synopsis of these cities, than this is a good tour. Gabrielle was an excellent guide, very informative and provided detailed information during the tours! Take his tour and come back for an extended stay!
V6097RWcindyf, 10/20/2025 6:00:43 AM
My husband and I had a wonderful tour with Gabrielle and Zanny to Siena and neighboring medieval towns!! Gabrielle was very knowledgeable and personable as a guide. I recommend this tour😍
mauricef592, 10/19/2025 12:32:08 PM
The trip was great, the guide Gabrielle was knowledgeable and was constantly getting the whole tour involved Quite a long day, which we did know about in advance, but we covered a lot of ground. Recommended as value for money.
- 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
- 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
- May be operated by a multi-lingual guide
- Please note that the given order of the visits may change
- Please inform us of any food intolerance or allergy in advance
- 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