San Gimignano, Chianti, and Montalcino Day Trip From Siena
Free Cancellation
4.3 (150)
from
EUR 138.00

11 hours


E-voucher


Multiple

Overview

Start with 8:30am hotel pickup, depending on the time of year. As the sights of Siena slip into the distance, you’ll notice the landscape turn into the undulating hills of Tuscany.

Your first stop in the region is the beloved hill town of San Gimignano, a UNESCO World Heritage Site. Enjoy free time here to wander the streets of its historical center, gazing at the medieval architecture, towers, piazzas, and artisan shops. San Gimignano produces the renowned vernaccia wine, and you’ll find plenty of enoteche (wine shops) around the streets.

Then, travel into the Val d’Orcia region of Tuscany where the winemaking village of Montalcino awaits. Next, you’ll head to the historic fortress town of Monteriggioni. Stop at a winery for lunch and a wine tasting. Savor a light meal of local cheese and salami, paired with Chianti wine.

Taste the esteemed Brunello di Montalcino wine, and learn about the town’s winemaking traditions.

Relax on the journey back to Siena, and finish your day trip with a hotel drop-off.

Operated by

myTour in Italy

Ratings & Reviews

Average Rating

4.32

/ 5

150 traveller ratings

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Great guided experience with Luca

Christina111196, Nov 2025

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.

Response from Host, Nov 2025

Dear Customer, Thank you for sharing your feedback with us! It’s great to hear you liked the wineries, cities, and beautiful Tuscan views. We hope to welcome you again soon for another wonderful experience! Best regards, My Tour In Italy

Buyer beware. Over booked and not what was advertised at all. Big waste of money

Tamara_L, Oct 2025

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

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Response from Host, Nov 2025

Dear Customer, Thank you for sharing your feedback with us! We strive to provide the best possible service to our guests and ensure that every tour is enjoyable and comfortable. We appreciate your comments and will communicate with the wineries regarding your feedback to understand what happened. Many other guests have taken this tour and have had positive experiences, so we will do our best to address any issues. We hope to have the opportunity to provide you with a better experience in the future. Best regards, My Tour In Italy

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

GrayJoan, Oct 2025

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.

Was my dream come true

Toni F, Oct 2025

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

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Response from Host, Oct 2025

Dear Customer, Thank you for sharing your feedback with us! We are very glad to hear that you enjoyed the tour and appreciate your kind words. Due to the fixed itinerary and the need to respect the return time to the destination, our schedule is limited to ensure everything runs smoothly and on time. We truly appreciate your understanding and are happy that overall, you had a good experience. We hope to welcome you on another tour soon! Best regards, My Tour In Italy.

Itinerary

  • San Gimignano 1300

    Free time in San Gimignano

    1 hour
  • Collegiata di Santa Maria Assunta - Duomo di San Gimignano

    During your free time opt to visit the Cathedral of San Gimignano

    15 minutes
  • Piazza Della Cisterna

    Free time in San Gimignano

    15 minutes
  • Palazzo Pubblico e Torre Grossa

    Free time in San Gimignano

    15 minutes
  • Strada Statale 222 Chiantigiana

    Lunch and wine tasting in a local winery in Montalcino

    1 hour
    Admission Included
  • Fortezza di Montalcino

    Free time in Montalcino

    1 hour
  • San Filippo Montalcino

    Free time in Montalcino

  • Val D'Orcia

    Spend some time in the stunning Orcia Valley

    1 hour
  • Siena

    Start your trip at Siena Station Ferrovia, where you will meet the staff. You will recognize them by their green shirt. You will travel by minivan.

    40 minutes
Meeting Point Map

Location

Address

53100 Siena, Province of Siena, Italy

Open Google Map

Experience

Highlights

  • Save yourself hours of planning travel logistics
  • Sample Chianti wine at a Montalcino winery
  • Travel through the idyllic Val d’Orcia region without self-driving
  • A small group means a more personalized experience
  • Inclusions

    • Travel in air-conditioned minivan for up to 8 people or minibus for up to 20 people
    • Expert multilingual escorts
    • Olive oil and balsamic vinegar sampling
    • Snacks
    • Alcoholic beverages
    • Tour of 2 wine estates, one of which is exclusive + 2 wine tastings

    Exclusions

    • Gratuities

    Additional Information

    • 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

    Guide Languages

    • English

    • Spanish

    • Italian

    Cancellation Policy

    • A full refund will apply if you cancel more than 24 hours before the activity start time.

    • No refund is possible if you cancel less than 24 hours before the activity start time.

    from
    EUR 138.00