Tuscan Countryside Day Tour: Wine Tasting and Visit to San Gimignano and Montalcino from Siena

151 Ratings

Siena

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Indulge in a full-day tour of the Tuscan countryside, including a wine tasting and visit to San Gimignano and Montalcino. Explore the stunning towers of San Gimignano and discover the renowned Brunello di Montalcino in the picturesque Orcia Valley.

Duration: 11 hours

Cancellation: 24 hours

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Highlights

San Gimignano 1300 - Enjoy leisure time in San Gimignano
Collegiata di Santa Maria Assunta - Duomo di San Gimignano - During your leisure time, consider visiting the Cathedral of San Gimignano
Piazza della Cisterna - Enjoy leisure time in San Gimignano
Palazzo Pubblico e Torre Grossa - Enjoy leisure time in San Gimignano
-…

What's Included

Expert multilingual escorts
Lunch
Olive oil and balsamic vinegar sampling
Alcoholic beverages
Meals
Tour of 2 wine estates, one of which is exclusive
2 wine tastings

What's Not Included

Gratuities

Additional Information

Experience an unforgettable day discovering Italy’s renowned hill-towns and exceptional wineries. Begin your journey in Siena and explore the medieval streets of San Gimignano. Enjoy the scenic vineyards of Chianti, sample the famous Brunello di Montalcino, and delight in local snacks, olive oil, and balsamic vinegar—all while traveling in a comfortable…

Location

Siena - Ferrovia

Meet our team at: Siena Stazione, Siena Province of Siena, Italy

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings

4.3

(151 Ratings)

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1 star

Christina111196

Nov 9, 2025

Great guided experience with Luca - Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Review provided by Tripadvisor

Rudy_m

Sep 9, 2025

Worth the money. Must do. - 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.

Review provided by Viator

Thuy_t

Jun 24, 2025

Tuscany tour - 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.

Review provided by Viator

Gwarnershoe54

May 22, 2025

Beautiful scenery - 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

Review provided by Tripadvisor

Toni

Oct 10, 2025

Was my dream come true - 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

Review provided by Tripadvisor

Grayjoan

Oct 14, 2025

See above - we felt it was over-priced and too much time spent in the bus. - 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.

Review provided by Tripadvisor

Tamara_l

Oct 20, 2025

Buyer beware. Over booked and not what was advertised at all. Big waste of money - Buyer Beware. This tour was a 3rd party vendor My tour 366, who rescheduled the tour and overbooked what was supposed to be an 8-12 semi-private tour to 28 people. The two wineries were not able to accommodate. we ended up in the production area at the last minute, not the tasting room. The bus driver initially pulled into a lovely winery only to back out and take us to another venue twice. The 1st venue clearly was not expecting us and was trying to set up last minute. we could not use the main restroom because there was another tour and we were ushered into some dirty back room bathroom. We were served bread which was moldy. The second tour same thing we pulled into a beautiful estate, only to back out and end up on a small production farm, they were actually working the harvest and it appeared we were fit in last moment. The wine maker came out and poured wine and asked people to come help him. The area we were sent to looked to be where the staff had their breaks. There was supposed to be a tasting for olive oil/balsamic vinegar, that did not happen. our guide when asked said, these things happen it is the busy season, well it is October and not peak season. Not for $668 for 4 people. Such a disappointment. you hear how wonderful Tuscany is, it was our 40th wedding anniversary, and a once-in-a-lifetime trip. I am not by any means a wine snob, but have been to some pretty nice wineries in Napa and Sonoma so I know what to expect. This was not even close. We booked with Viator because of their reputation. Our guide lied to the tour company and said everyone was happy. I have so many photos that I will be sharing on Social media so noone else wastes their money and time. Keep looking if you want that fabulous once in a lifetime Tuscany experience you dreamed of, this is not it

Review provided by Viator

Stavroula_p

Oct 1, 2025

disappointment - The first wine tasting did not take place in a winery. The place we have been WAS NOT A WINERY, they did not expect us, it was dirty inside out and looked more as a trap. Further, in Montalcino we stayed too little, because we spent too much time in the trap. In the last wine tasting, which took place in a real beautiful winery, we arrived almost at their closure.

Review provided by Viator

Danil_k

Sep 22, 2025

Not a guided tour, just a ride! - Misrepresentation of the tour! No guide, just a driver, who doesn't speak a word of English... We could drive there ourselves

Review provided by Viator

Suzi_m

Jun 1, 2025

First winery was nice... - First winery was nice though it was an extra $20 for lunch which was very confusing. Tour guide wasn’t friendly and slept a lot. Second winery was horrible.

Review provided by Viator

Check Availability

From $162

up to 8 guests

1 - Adult