Exclusive Tuscany: Siena, San Gimignano & Winery Feast
Price From $221.19 per person
Lowest Price Guarantee
Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo, and stunning Gothic landmarks. Taste local specialties before heading to San Gimignano, the medieval town of towers, where you’ll have time to wander its enchanting streets. As the sun sets, continue to a scenic winery in the Chianti countryside for a typical Tuscan dinner and wine tasting in an unforgettable location. Looking for the full Tuscan experience? Upgrade to our Tuscany Grand Tour: a full-day adventure that also includes a visit to Pisa and its iconic Leaning Tower, plus a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and embrace the art, history, and flavors of Tuscany from dawn to dusk.
Reviews
Reviews and Rating (Tripadvisor)
5 stars
4 stars
Reviews by Tripadvisor travelers
Excursion612312, 11/28/2025 2:40:59 PM
Great tour guide Lorenzo. Enjoyed both cities and the winery. All was planned well we had a good time. We went in November
Maryann S, 11/12/2025 3:00:08 PM
Grace was informative and very personable. She spoke of the history of the region as we dove through each region. She elicited questions in a friendly manner wanting to know more about our group to enrich her presentation
757kemberlys, 11/7/2025 2:54:11 PM
Excellent tour! Winery was awesome! Winery owner is the sweetest! This was such a great experience! I learned so much about the making of the wine and what to pair each wine with. AND… the dinner was AMAZING!
494karthika, 11/7/2025 2:53:28 PM
Excellent guided tour matched with eccellente dinner and Wine testing at winery. This was in Seina and San Giammamo. Personable and detail oriented
Roam58802392996, 10/29/2025 2:02:29 PM
Was great! Thanks claudia! Afternoon tour end of october was a bit late but it was still great!! Especially the wine farm at the end!!
X6758KSjimmyb, 10/25/2025 4:06:33 PM
Such a great tour and experience, winery part and family vineyard was fabulous! The small towns were a nice place to visit away from Florence. Smaller and less people.
718randir, 10/22/2025 3:46:49 PM
Lorenzo was an amazing tour guide! So patient, on time, and knowledgeable. Answered all our questions we had on the way! All of the stops on the tour were beautiful and amazing! I would love to some back and do it again some day.
cindyhall04, 10/19/2025 3:47:12 PM
Guides were incredible and the locations chosen were breathtaking. Small note for feedback was the van was quite small and felt squishy but overall really glad we went and would do it again!
Bryan T, 10/18/2025 4:09:26 PM
Guides were friendly and knowledgeable. Sienna and San Gimignamo are just like the old Italian towns you see on TV. Little stone streets with shops and restaurants all around with all the activity surrounding the squares. Dinner at the winery was really nice with food and reasonably priced wines if you choose to purchase. The son of the owner was there to tell us about each wine. No high pressure sales either. Only issue was the bus we were on was really cramped with little to no leg room, and I am average height. Also, A/C on bus was a little lacking.
Alejandra P, 10/18/2025 3:52:39 PM
Peter was an amazing guide tour! Provided lots of information and historical facts about the sites we visit. The only thing to improve will be to have free time in Siena for a coffee or shopping.
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- The tour operates regardless of weather conditions
- Semiprivate Tuscany Grand Tour Option: Choose the Grand Tour upgrade for a full-day experience starting at 8:00 AM. Discover the highlights of Tuscany in one unforgettable journey: visit Siena with a guided walking tour and a surprise tasting, enjoy free time in the medieval town of San Gimignano, savor a traditional Tuscan lunch, then continue to Pisa to admire the stunning Piazza dei Miracoli and the iconic Leaning Tower (tower tickets not included). The experience includes round-trip transportation from Florence in a luxury Mercedes minivan with free Wi-Fi, an English-speaking driver/tour leader, and all the charm, history, and flavor of Tuscany in one complete itinerary.
Departure point
Via dei Vagellai 22R, at the corner of Piazza Mentana (across from the Arno River)Return details
Discover the best of Tuscany in one magical afternoon! Start from Florence and travel in a luxury minivan through the rolling Chianti hills. Enjoy a guided walking tour of Siena, exploring its Contrade, Piazza del Campo, and stunning Gothic landmarks. Taste local specialties before heading to San Gimignano, the medieval town of towers, where you’ll have time to wander its enchanting streets. As the sun sets, continue to a scenic winery in the Chianti countryside for a typical Tuscan dinner and wine tasting in an unforgettable location. Looking for the full Tuscan experience? Upgrade to our Tuscany Grand Tour: a full-day adventure that also includes a visit to Pisa and its iconic Leaning Tower, plus a Tuscan lunch. Follow in the footsteps of the Grand Tour travelers and embrace the art, history, and flavors of Tuscany from dawn to dusk.Redemption
• Rain Policy: The tour operates regardless of weather conditions. • Please note that starting from March 2025, the sole meeting point will be: Florence, Via dei Vagellai 22 (red), at the corner of Piazza Mentana (across from the Arno River) • Those who arrive late will not be entitled to a refund, therefore we kindly ask all our guests to arrive at the meeting point 15 minutes in advance24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund