Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Badge of ExcellenceSiena, Italy
San Gimignano Chianti and Montalcino from Siena
  • 11 hours
  • Mobile ticket
  • Offered in: English

Overview

Visit San Gimignano and Montalcino on a small-group day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Montalcino winery plus samples of Chianti and Brunello di Montalcino wine.
  • Explore San Gimignano by foot and admire its medieval towers
  • Stop for lunch and Chianti wine at a Montalcino winery
  • Travel through the idyllic Val d’Orcia region
  • A small group means a more personalized experience

What's Included

  • Travel by minivan with air conditioning for a maximum of 8 people
  • Expert multilingual escorts
  • Wine tasting and Lunch consisting of typical Tuscan dishes
  • sliced cured meats and typical salami
  • Gratuities

Meeting And Pickup

Meeting point

  • Via Giuseppe Garibaldi, 72
    Via Giuseppe Garibaldi, 72, 53100 Siena SI, Italy

    Meet our driver in front of Hotel Minerva

Start time

08:30 AM

End point

This activity ends back at the meeting point.

What To Expect

Start with a 7:30am or 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.

San Gimignano 1300

1 hour Admission Ticket Free

Collegiata di Santa Maria Assunta - Duomo di San Gimignano

15 minutesAdmission Ticket Not Included

Piazza della Cisterna

15 minutesAdmission Ticket Free

Palazzo Pubblico e Torre Grossa

15 minutesAdmission Ticket Not Included

Chianti Road

1 hour Admission Ticket Included

Fortezza di Montalcino

1 hour Admission Ticket Free

San Filippo Montalcino (Pass By)

Val d'Orcia

1 hour Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Customers must be able to climb and descend stairs.
  • Vegetarian option is available for lunch, please advise any specific dietary requirements at time of booking
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

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Reviews

4.5
110 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
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Reviews by Viator travelers.
Showing 1-10 of 110 reviews
Unreal
Anna_R, Nov 2023
This was an unbelievable trip! Everything we saw was just breathtaking. The views were spectacular. We had a lot of free time to roam around and see each part. Th guide was very accommodating and even shifted few things to ensure we get the best views before the sun went down.
Response from Host, Nov 2023
Dear Customer, Thank you for taking your time and sharing the feedback of your experience with us. We are glad to know that you enjoyed the tour and had an amazing time with the guide. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.
Enjoyed being part of a...
Elaine_S, Oct 2023
Enjoyed being part of a small tour group. The lunch was good. Found the tour leader hard to hear and understand. Was a lot of driving involved. Would prefer less driving and more sight seeing.
Response from Host, Oct 2023
Dear Customer, Thank you for taking your time and sharing the feedback with us. We are glad that you liked the tour in general and enjoyed the lunch. Sorry to know that you found difficulty in hearing the guide. This is a long tour, and it is written on its description, too, that it includes long hours of travelling. Hope to have you again in our upcoming tours in the near future, in order to show you our service improvement, hoping we will get a full star rate next time and leave a better impression to you. Best regards, My Tour in Italy team.
Great guide and beautiful scenic experience
Patricia_S, Oct 2023
Daniel our guide and driver was knowledgeable and kind. He allowed us free time after interesting discussions regarding the area. Highly recommend this tour!
Response from Host, Oct 2023
Dear Customer, Thank you for sharing your feedback with us. We are happy to know that you enjoyed the tour and had a good time with our staff. Thank you for recommending this tour to other customers too. Hope to have you again on our upcoming tours in the near future. Best regards, My Tour in Italy team.
Great excursion - thoroughly enjoyed!
williamsness, Oct 2023
We had a fantastic day, met some great people and enjoyed some lovely wine! Vincenzo was a fantastic guide and spoke fluent English. The trip to San Gimignano was early in the day, so we had the place to ourselves (before the hoards arrived). The town is beautiful and the views from the high walls were stunning - especially as the low cloud produced some atmosphere to our photos. The two vineyards were informative and interesting - providing the opportunity to purchase, but without any pressure. Lunch was good too. Cheese, meats and bread to start. Pasta dish with ragu to follow. With wine to compliment (including a bottle of Prosecco, kindly purchased by one of our party). A visit to Montalcino added to the experience - another medieval town with some beautiful architecture. We both had a wonderful day!
Response from Host, Oct 2023
Dear Customer, Thank you for sharing this feedback and letting us know about your experience. Glad to know that you enjoyed the tour and had an amazing experience with our team. Thank you for the good opinion you have created for the guide, and many thanks for those words of appreciation. We appreciate for all this explanation of the tour's itinerary and for all those details given. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.
Day trip included wine
Robert_M, Oct 2023
Great tour. Long day but worth it. Group was fun. Wine tasting was great. Nice seeing other towns in the region. Worth the money
Response from Host, Oct 2023
Dear Customer, Thank you for sharing your feedback with us. Glad to know that you liked the tour and enjoyed every part of it. Hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.
Mediocre
josephine_a, Oct 2023
Beautiful places and nice wine tastings, but some issues. Our van was old and rickety and lacked a seatbelt for one participant. Dangerous situation for highways and sudden need to brake. The guide was nice but not at the level of expertise that I thought I paid for.
Response from Host, Oct 2023
Dear Customer, Thank you for taking your time and sharing the feedback of your experience with us. Glad to know that you liked the destinations and wine tasting overall. We are sorry for this issue that disturbed you and caused you to not feel so safe. We can confirm that on our tours, the vehicles are always checked and have regular maintenance. Probably it might have been something that the seat belt might have been stuck in some way, but we have checked and everything had worked just fine. The roads on this tour are not dangerous at all as they are inside country roads with not so much traffic and do not permit to go so fast. Our drivers are very careful on driving vehicles and do exceed the speed limit. Sorry for all the issues disturbing you and making you feel unsatisfied. Thank you for your understanding. Best regards, My Tour in Italy team.
Just right day trip!
Wendy_E, Oct 2023
This was a perfect way to see Tuscany when you aren’t traveling by car. Seeing the towns and the countryside and stopping for some wine tasting along the way checked all the boxes.
Response from Host, Oct 2023
Dear Customer, Thank you for sharing your feedback. We are happy to know that you enjoyed the tour in general, at each stop, and we hope to have you again in our upcoming tours in the near future, in order to give you more experiences like this one. Best regards, My Tour in Italy team.
scenic excellence
Bernice_W, Oct 2023
beautiful views of countryside were exactly what I wanted, an excellent driver, taste of some wines esp Brunello de Montalcino
Response from Host, Oct 2023
Dear Customer, Thank you for sharing your feedback with us. Glad to know that you had a good time on the tour and liked our driver too. Hope to have you again in our upcoming tours in the near future, hoping we will get a full star rate next time. Best regards, My Tour in Italy team.
Tuscan tour
Janice_S, Oct 2023
Beautiful scenery. Guide gave interesting facts about the area- vinyards, history etc Lunch was very good. Time on your own was worthwhile to suit individuals. Only suggestion would be to have microphone in van as not able to hear driver at back
Response from Host, Oct 2023
Dear Customer, Thank you for sharing your feedback with us. We are glad that you have liked every detail of the tour in general, and you enjoyed the tour itself. Thank you for your recommendation, we will take note of it in order to improve our service. Hope to have you again in our upcoming tours in the near future, so we can show you our service improvements and give you another good experience, hoping we will get a full star rate next time. Best regards, My Tour in Italy team.
Recommend this day trip.
Tracee_D, Sep 2023
Fabio was an excellent guide. He shared interesting information on the towns and area and was always very pleasant. The wineries and lunch were both very enjoyable.
Response from Host, Sep 2023
Dear Customer, Thank you for sharing your feedback with us. Glad to know that you enjoyed the lunch and the time in wineries. Many thanks for appreciating our guide's work and for the good words for him. Hope to have you again in our upcoming tours in the near future. Best regards, My Tour in Italy team.
An enjoyable scenic day trip.
Anonymous, Aug 2023
I always wanted to visit San Gimignano and now very happy that have been. Montalcino was also a nice place to visit. The wine tasting and amazing views over Chianti was also an enjoyable experience.
Response from Host, Aug 2023
Dear Customer, Thank you for sharing your feedback with us. Happy when we hear that our customers enjoy the tour. Hope to have you again in our upcoming tours in the near future, to have another enjoyable experience. Best regards, My Tour in Italy team.
Gorgeous Views, Bumpy Ride!
Ashley_M, Aug 2023
I absolutely loved stopping in all the wineries and small towns through out Tuscany. It was gorgeous, the pours were heavy, and the group was great! The only thing stopping this from being five starts was the fact that we sat in the back of the van as it drove and couldn’t hear a single word being said by our guide Daniel, as the terrain was rough and he was incredibly soft spoken.
Response from Host, Aug 2023
Dear Customer, Thank you for sharing your feedback with us. Glad to know that you loved the wineries and enjoyed your time on the tour. Sorry for the issue you have had on the van, by not hearing well the guide, we took note of this. Hope to have you again in order to show you our service improvements and give you a better experience, hoping we will get a full star rate next time. Best regards, My Tour in Italy team.
Wonderful winery tour
Christine_N, Aug 2023
Excellent value! You cover a lot of ground in a day. Our driver, Vincenzo, had excellent advice for what we should see in each of the stops. Lunch was delicious and we sampled a good amount of wine
Response from Host, Aug 2023
Dear Customer, Thank you for sharing your feedback. Happy to know your good opinion about the tour and that you liked every part of the tour in general. Hope to see you again in our upcoming tours in the future. Best regards, My Tour in Italy team.
Fantastic day... worth every penny!
AliceNugent, Aug 2023
ALL was amazing. Our guide was fantastic. San Gimignano was even better than expected. Lunch was great and all the wineries were excellent. The day went by so quickly.
Response from Host, Aug 2023
Dear Customer, Thank you for sharing your feedback with us. Glad to know that you had an amazing experience and liked the guide. Thank you for choosing MyTour to travel through Italy. Hope to have you again in our upcoming tours in the future. Best regards, My Tour in Italy team.
Our driver, Fabio was...
Nancy_S, Jul 2023
Our driver, Fabio was incredible telling us about the Tuscan area and places that we were going to—very personable and made the day very enjoyable! The places we went were awesome!
Response from Host, Jul 2023
Dear Customer, Thank you for sharing your feedback with us. We are glad to know that you had an enjoyable day with our driver Fabio. Happy to know that you liked the tour. Hope to see you again in our tours in the future. Best regards, My Tour in Italy team.
Dreamy Tuscany
Vaida_T, Jul 2023
Tour was amazing! My dream came true to see beautiful landscapes with cypress trees that brought me to Tuscany in the first place. Nature there so beautiful and the wineries we visited were in the most beautiful landscape spots! Wineries in the nature were my favourite parts of the tour but I loved little villages we visited as well. You have enough time to roam around and enjoy architecture or grab a snack.Vincenzo is great guide that clearly loves his job and provides lots of interesting information! Having been on several tours in Italy I would recommend to do this one !!!
Response from Host, Jul 2023
Dear Customer, Thank you for sharing this feedback. We are glad to hear about your fantastic experience on our tour. Wineries are result of our seraching for the best place, in order our customers can enjoy their time there. Thank you for the good words for our guide, Vincenzo. He is one of the best employes on our staff. Happy to hear that you had a fun time in every destination. Looking forward to having you again on our tours on the future. Thank you for recommending this tour to other people. Best regards, My Tour in Italy team.
A great day out!
Mark_W, Jul 2023
Great host, great sites and great travelling companions … not to mention the wine!! Really enjoyed seeing the countryside as well.
Response from Host, Jul 2023
Dear Customer, Thank you for sharing your feedback with us. We are glad to hear that you have liked every detail about this tour. Thank you for choosing us for this experience. Hope to have you again in our upcoming tours in the future. Best regards, My Tour in Italy team.
Superb trip, very detailed and excellent quality time!
Mona_S, Jul 2023
Best trip to see Siena, it was a great time and we saw a lot that we could not have seen otherwise. Our tour guide driving the bus was excellent and friendly. Customer support has been outstanding with respond to messages coming instantly.
Response from Host, Jul 2023
Dear Customer, Thank you for your positive feedback. We are very glad to hear that you had a great time while our tour. Thank you for appreciating our staff's work. Our costumers are our priority and we always do the best to give them a qualified service. Hope to see you again in our other tours in the future. Best regards, My Tour in Italy team.
Great day out
Helen_K, Jul 2023
Great day out, got to see a lot of Tuscany countryside, taste many wines and a nice lunch. Also had an hour and a half in San Gimignano. Good value for money.
Response from Host, Jul 2023
Dear Customer, Thank you for sharing ypur feedback with us. We are glad to hear that you've enjoyed the time on tour. The wine and lunch are results of doing our best in searching the best places for our customers to eat. Hope to see you again in our tours, in order to give you another great experience. Best regards, My Tour in Italy team.
Fun!
Ashley_S, Jul 2023
Our tour director was wonderful! We were able to see so many things. I do wish, however, we had more time at the winery and one less city.
Response from Host, Jul 2023
Dear Customer, Thank you for your positive feedback. We are happy that you enjoyed the tour. As per the time in each destination, we try to respect our itinerary. Hope to see you again. Best regards, MyTour in Italy team.
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up to 24 hours before the experience starts (local time)

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