Unforgettable Tuscan Trio: Chianti Wine & Hilltop Towns
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Enjoy a wine tasting and optional typical lunch in a winery on a full day tour of the Tuscan countryside. Visit San Gimignano a real jewel famous thanks to its stunning towers and discover Orcia Valley with a visit to Montalcino, known all over the world for the production of Brunello di Montalcino.
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Reviews by Tripadvisor travelers
GrayJoan, 10/14/2025 5:28:11 AM
Below are the details of our booking: San Gimignano, Chianti, and Montalcino Day Trip from Siena Guided tour Date & time Mon, Oct 13, 2025 • 08:30 AM Language English - Guide Booking ref. 1324690867 Travellers Joan Wright • 2 adults Activity provider myTour in Italy Powered by Ticket barcode 1324690867 Although this tour was not planned in our budget, we decided to book the 11 hour tour. At a cost of nearly $250 each, AUD, we had hoped to have value for our money. We were very disappointed on many levels. We tried to write a more detailed review, but the restriction of the max number of characters, did not allow for this. Therefore we will continue here. We were not impressed with the guide who talked incessantly with the driver, who was driving with one hand and turning his head constantly towards the guide. We found this stressful and didn't feel comfortable or safe. Also, we thought just being left to our own devices to look around San Gimignano without a guide was not what we expected having been on similar tours before at this level. The first winery was interesting as they seemed not to be expecting us. We were disappointed that we were served only bread soaked in olive oil! The trip to the 2nd winery was very long and we heard from fellow participants that it was not the winery we had been promised. Again the only food for this expensive tour was bread and olive oil! The stop off at Montalcino was disappointing as most shops were closed at that time of day. Then to travel back in the dark was not a good ending to our day. Fellow travellers felt the same.
Toni F, 10/10/2025 6:53:09 AM
The tour was a great opportunity to see some beautiful places in Tuscany. However was a bit disappointed with no cheese and salami as stated on the tour at the wine tastings. But overall the experience of two wine tastings at two beautiful vineyards was amazing. I always dreamed of being able to sit in the vineyards sipping on the delicious wines and it came true. The hosts at the vineyards were amazing and it was good to learn how they make the wines. I do recommend although would prefer to spend more time at the vineyards
Rudy_M, 9/9/2025 3:17:25 AM
Wonderful trip with a great tour guide Veleaka. This was an 11hr tour and we were never bored. It was a leisurely trip with the best views of Tuscany we saw while in Italy.
Thuy_T, 6/24/2025 4:17:01 AM
We enjoyed our day tour to the vineyards and the rides of Tuscany region !!! Highly recommended this tour if you have a few days to Siena or just one day to spare from Florence.
gwarnershoe54, 5/22/2025 3:24:31 PM
The country side was beautiful and the two wineries were amazing and different. There were some mix ups in our visits and timing but our tour guide handled it well. Highly recommend this tour
David_C, 5/20/2025 4:22:50 AM
Lovely day and easy itinerary - starts early but it's for the best - starting in san Gimignano before crowds arrive, then moving on to a great winery - lunch is an option there, unless you're bringing food or buy something to go in san Gimignano, this is really the only lunch option so I recommend it. The tour itself is a nice mixture of walking and wine interspersed so you never feel overly tired. Vincenzo was an excellent guide and really added a lot of history to what we saw. Great day overall highly recommend
Alisa A, 5/12/2025 12:15:36 PM
I was really excited to take this tour. San Gim and Montalcino are two of my favorite towns, and I love Vernaccia & Brunello wines. First, the Sprinter a/c didn't work. The van was stuffy and hot, and this was early May. Second, our tour guide was checked out. She didn't seem to want to be there. There was no explanation of where we were going, no history, no enthusiasm. The first winery was a disappointment. It was very industrial. Not the Tuscan experience you want when you go to Italy. The wines were good, and the sommelier did a good job. Lunch was rigatoni with a meat sauce for €20. It was o ovecooked and so salty no one ate it. The 2nd winery was more of what I had hoped. The sommelier did a great job, but the wines were not very good. I actually felt sorry for him. On the plus side, we met some nice people, and any day in Tuscany is a good day. I do not recommend this tour.
Lauren_M, 5/7/2025 5:40:59 PM
Our driver was so friendly and knowledgeable about the region. The itinerary was put together so well giving us time to explore yet keeping us moving along to view four towns. Starting in San Gimignano, moving onto the winery in Chianti for our first tasting with lunch. We learned a lot about the wine and the region. We shared a Great experience with one other couple who we just met that day.
j9hoaster, 5/2/2025 3:29:37 AM
We had a wonderful time touring Chiani and Brunello regions. Vincento was very knowledgeable and even stopped for photos. Luxury van made for a very nice ride. Plenty of time to tour San Gimignano.
marciab182, 3/27/2025 10:34:36 AM
Great wine tasting experiences, guide Mikaelo was very knowledgeable with history and culture of the area. My only disappointment was that we were dropped off for the towns & our guide didn’t go with us. For the cost of the tour we purchased, I was surprised. I do very much appreciate him taking us on as a tour at the last minute as our previous tour cancelled.
- 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
- Customers must be able to climb and descend stairs.
- Vegetarian option is available for the optional lunch, please advise any specific dietary requirements at time of booking
Departure point
Meet our team at: Siena Stazione, Siena Province of Siena, ItalyReturn details
Enjoy a wine tasting and optional typical lunch in a winery on a full day tour of the Tuscan countryside. Visit San Gimignano a real jewel famous thanks to its stunning towers and discover Orcia Valley with a visit to Montalcino, known all over the world for the production of Brunello di Montalcino.Redemption
• For any urgent communication please contact +390577236330 • Arrive 15-minutes before departure for check-in24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund


















