Exclusive Tuscany: Siena, San Gimignano & Winery Feast
Price From $221.19 per person
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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
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.
Michael_W, 10/17/2025 12:48:23 AM
It was a nice ride through the part of Florence that you don’t see when downtown. Very beautiful. Guide was good energy and sense of humor.
sbenbow, 10/14/2025 4:31:10 PM
We had a fabulous experience with Gracie on our wine tasting tour of Sienna & San Giovanna she has been a wonderful guide full of information n great stories of the history of both towns followed by an authentic dinner at the factore de bagnolo with delicious wines to finish off the night would highly recommend Gracie towns of Italy for a great day !
R5804LMwilliamh, 10/11/2025 5:05:38 PM
Really enjoyed the day. San Gimignano was incredible, and we would have happily stayed longer. Lorenzo was a knowledgeable host and took great care in us. Highly recommend this tour.
Norbert M, 10/11/2025 3:38:30 PM
Just a wonderful tour with friendly and informative Lorenzo. Dinner and wine & olive oil tasting were the perfect finishing touch! Well done!
Trip10028037196, 10/11/2025 3:37:12 PM
Very enjoyable and informative tour with a great meal and wine-tasting experience. Loved the medieval character of San Gimignano
I9193RTrosec, 10/10/2025 5:23:25 PM
Our tour of Siena, San Gimignano, and a boutique winery was amazing. This portion of our Italy trip was one of the highlights. The tour was thoughtfully organized and a perfect way to experience the heart of Tuscany. Our guide Heather was a pleasure. Heather was well-educated and conveyed passion for the region. He was engaging, light-hearted, and perfectly timed, making the day educational and fun. He provided practical tips when visiting the area and his attentiveness didn’t go unnoticed — he was always checking in to make sure everyone was comfortable, and going the extra mile to personalize the experience. Another highlight was the hospitality of the proprietor of the winery. She was engaging and fun. Book this trip.
barbaradA9644NU, 10/8/2025 4:04:47 PM
An excellent tour with s wonderful dinner and wine tasting. The hosts were extremely gracious and knowledgeable. We would highly recommend this tour.
- 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