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San Gimignano, Chianti, and Montalcino Day Trip from Siena

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Siena, Italy
San Gimignano, Chianti, and Montalcino Day Trip from Siena
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Free cancellation
Up to 24 hours in advance. Learn more
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Safety measures
icon11 hours  (approx.)
Hotel pickup offered
Mobile ticket
iconOffered in: English and 2 more
Good for avoiding crowds

Overview

Visit San Gimignano, Monteriggioni, and Montalcino on a 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 Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.
  • Day trip to Tuscany’s hill towns from Siena
  • Explore San Gimignano by foot and admire its medieval towers
  • Stop for lunch and Chianti wine at a Monteriggioni winery
  • Travel through the idyllic Val d’Orcia region
  • Sample Brunello di Montalcino wine in Montalcino
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Pick up service
Travel by minivan with air conditioning for a maximum of 8 people
Expert multilingual escorts
Wine tasting and Light Lunch consisting of typical Tuscan dishes
Snack with sliced cured meats and typical salami
Drop off service
Gratuities
This operator has two meet-up options available. You can either meet at the departure point below or select a location for pick-up.
Piazza Antonio Gramsci , Piazza Antonio Gramsci, 53100 Siena SI, Italy

If pickup is not required please meet our staff in front of Bar La Lizza in piazza Antonio Gramsci a Siena

Hmm...we can’t seem to find this place. Please check the spelling, or choose another location.

8:30 AM
This activity will end right where it started.Pick up and drop off are included for Accommodations located within 20km from the center of Siena. Please tell us Accommodations details at the time of booking - exact pickup time will be reconfirmed after booking. Our driver will wait for you in front of the main entrance.
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.

Next, you’ll head to the historic fortress town of Monteriggioni. The hill town is encircled by intact medieval walls, beautifully preserved from the 12th century. Hear how Dante likened the walls’ towers to the Giants of Inferno in his Divine Comedy as you enter the town, then make your way to a winery for lunch. Savor a light meal of local cheese and salami, paired with Chianti wine.

With your appetite sated, you’ll travel into the Val d’Orcia region of Tuscany where the winemaking village of Montalcino awaits. 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.
Itinerary
Stop At:  
San Gimignano 1300
Free time in San Gimignano
Duration: 1 hour 
Admission Ticket Free
Stop At:  
Collegiata di Santa Maria Assunta - Duomo di San Gimignano
During your free time opt to visit the Cathedral of San Gimignano
Duration: 15 minutes
Admission Ticket Not Included
Stop At:  
Piazza della Cisterna
Free time in San Gimignano
Duration: 15 minutes
Admission Ticket Free
Stop At:  
Palazzo Pubblico e Torre Grossa
Free time in San Gimignano
Duration: 15 minutes
Admission Ticket Not Included
Stop At:  
Cantinetta di Monteriggioni
Free time in Monteriggioni
Duration: 40 minutes
Admission Ticket Free
Stop At:  
Chianti Road
Lunch and wine tasting in a local winery in Montalcino
Duration: 1 hour 
Admission Ticket Included
Stop At:  
Fortezza di Montalcino
Free time in Montalcino
Duration: 1 hour 
Admission Ticket Free
Pass By:  
San Filippo Montalcino
Free time in Montalcino
Stop At:  
Val d'Orcia
Spend some time in the stunning Orcia Valley
Duration: 1 hour 
Admission Ticket Free
  • Confirmation will be received at time of booking
  • Customers must be able to climb and descend stairs. A small amount of walking is involved to reach Monteriggioni Castle as it is uphill.
  • Pickup and drop off are included for Hotels located within 20km from the center Siena. If your accommodation is outside, please consider that the meeting point will be from: Siena, Piazza Gramsci in front of Bar La Lizza
  • 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
  • OPERATED BY myTour in Italy
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.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What is the policy on face masks and attendee health during San Gimignano, Chianti, and Montalcino Day Trip from Siena?
A:The policies on face masks and attendee health are:

  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Face masks provided for travelers
  • Temperature checks for travelers upon arrival
See all safety measures taken by San Gimignano, Chianti, and Montalcino Day Trip from Siena.
Q:
What is the policy on sanitization during San Gimignano, Chianti, and Montalcino Day Trip from Siena?
A:The policies on sanitization are:

  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Gear/equipment sanitized between use
  • Transportation vehicles regularly sanitized
See all safety measures taken by San Gimignano, Chianti, and Montalcino Day Trip from Siena.
Q:
What is the social distancing policy during San Gimignano, Chianti, and Montalcino Day Trip from Siena?
A:The policy on social distancing is:

  • Social distancing enforced throughout experience
See all safety measures taken by San Gimignano, Chianti, and Montalcino Day Trip from Siena.
Q:
What measures are being taken to ensure staff health & safety during San Gimignano, Chianti, and Montalcino Day Trip from Siena?
A:The policies on staff health & safety are:

  • Guides required to regularly wash hands
  • Regular temperature checks for staff
  • Paid stay-at-home policy for staff with symptoms
See all safety measures taken by San Gimignano, Chianti, and Montalcino Day Trip from Siena.

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Reviews

4.5
star-4.5
46 Reviews

Reviews by Viator travelers

We perform checks on reviews

Showing 1-10 of 46 reviews
star-5
Excellent tour
Barbara_S
, Jul 2022
This is an excellent tour with lots of time to properly visit each site and enjoy Tuscany countryside. Excellent wine and food tasting as well. We loved every minute of the trip and our tour guide, Vincenzo, was marvelous! Highly recommended.
1 traveler found this review helpful
star-5
Great time
Josh_C
, Jul 2022
Our guide Vincenzo was fantastic. He really made the trip. I loved the wines also. His gelato recommendation was spot on.
star-5
We had a great time!
Jesper_V
, Jul 2022
We had a great time on this tour! Our guide was very friendly and told us the best places to see in the towns we went to visit. The wineries were great and authentic as well, we even bought some bottles to take home! The tour was very much worth the price, we had an awesome time!
icon Response from Host , Jul 2022
Dear Jesper, Thank you so much for sharing your experience with My Tour. Our goal is 100% customer satisfaction and it sounds like we achieved that goal with you. Looking forward to have you back again in the future. Best Regards My Tour
star-1
Only informed us 12 hours...
Emily_M
, Jul 2022
Only informed us 12 hours beforehand that they wouldn’t pick up or drop off from our hotel because all of a sudden it was outside their radius so we couldn’t go. Still trying to get a refund from Viator. Was really disappointed to miss out.
icon Response from Host , Jul 2022
Dear Emily Greetings from myTour in Italy! The pick up/drop off service it’s included if your hotel is no more than 10km from Piazza Gramsci, unfortunately your hotel was more , so we couldn’t organize it. Or you could have had this service with extra charge We remain at your information for further information Best Regards myTours in Italy
star-5
Fabio the great
djttdft824
, Jul 2022
FABIO, our tour guide made this trip 110/100. He was beyond amazing, explained the history, culture, wine, everything with such enthusiasm. The stops are great, two wineries, generous lunch, two cities, and plenty of free time in the cities to roam, and partake in additional tastings if you prefer, which we did! Fabio also went out of the way to get us to some very nice scenic lookouts that were off the beaten path! Highly recommend you ask for Fabio, he really made our tour fun!!
star-5
Don't miss it! Excellent tour in all aspects.
Ana_W
, Jun 2022
The tour is so well organized that it was an incredible way to visit so many places and spend a good amount of time on each of them, in such a small amount of time. The wine tastings were fantastic, people friendly, and the wineries were beautiful. The tour guide was friendly and made several adjustment to satisfy everybody on the tour. It's a small tour which makes it more personalized
icon Response from Host , Jun 2022
Dear Customer, We appreciate you for choosing us and taking this tour with us. It is so nice to know that our team helped you to have a wonderful journey. Best Regards My Tour
star-5
Best tour for sightseeing and wine tasting
Diana_W
, Jun 2022
Luca was an amazing tour guide. Friendly, accommodating and just wanted to ensure we were all enjoying our day. Our van was making rattling noises around the front vent area and the sliding door needed an extra push to open so during our lunch he surprised us and switched out vehicles! We had plenty of time to enjoy all the stops and the two wineries we visited were very different yet great experiences. The last one was my favorite. We loved the history behind Abbadia Ardenga and their wine was delicious.
icon Response from Host , Jun 2022
Dear Diana , It is so nice to know that our team helped you to have a wonderful journey. Will be our pleasure to have you back again in the future. Best Regards My Tour
star-5
Tour
Diogo_C
, Jun 2022
Fábio was fantastic and provided an amazing tour! From the trip to the places we visited as well as the wine tasting! 100% recommended!!! Greetings from Portugal
icon Response from Host , Jun 2022
Dear Customer, Thank you so much for sharing your experience with My Tour. Our goal is 100% customer satisfaction and it sounds like we achieved that goal with you. Looking forward to have you back again in the future. Best Regards My Tour
star-5
Great 👍
Bob_D
, May 2022
Lorenzo was a terrific guide. The whole tour was excellent. Wineries were very good with explanations of their history
1 traveler found this review helpful
star-5
Awesome!
Spencer_P
, May 2022
It was an awesome tour and our driver was amazing! Would highly recommend to anyone in the area, very prompt in communication.
star-4
The people in our group...
Mary_D
, May 2022
The people in our group and the choice of wineries. The only thingbi would suggest is for the guide to give more info on the places before we explore on our own
icon Response from Host , May 2022
Dear Mary, thank you so much for your review. We're glad to hear from you that you enjoyed this experience with our team. Hope to see you again on another tour all around Italy!
star-4
Great way to see the local sites
NicolaBooth
, Apr 2022
A fantastic way to view so many places in such a small amount of time. Our host was friendly and a great tour guide on our drives to locations. Everything was well organised and we our group had private tasting sessions at each vineyard
icon Response from Host , Apr 2022
Dear Nicola, thank you so much for your positive feedback. We appreciate it! We're glad to hear that you spent such a lovely time in Tuscany with our team. Hope to see you again on another tour all around Italy! Thank you
star-5
Great and fun afternoon!
Richard_O
, Sep 2021
Our all day tour was cancelled but we were offered a half day wine tasting as an alternative. Duccia was a knowledgeable and enthusiastic guide! We laughed and learned a lot. We visited two very memorable wineries that helped us understand the Brunello wine culture.
icon Response from Host , Sep 2021
Dear Richard, thank you for your feedback, we're glad to hear you enjoyed our tour. We're happy you appreciated our staff service! Thank's a lot! Have a nice journey here in Italy!
star-5
A really exciting excursion with two wine tastings
Markus_S
, Sep 2021
A really exciting excursion with two wine tastings. Including snack & wonderful insights into the landscape & villages of Tuscany! Really to be recommended! We met exciting people from all over the world at the tastings. Duration (11 hours) was perfect. We were even picked up at the hotel. :)
icon Response from Host , Sep 2021
Thank you for your feedback, we're glad you spent such a lovely time with our staff in the amazing region of Chianti. Hope to see you again with us all around Italy! Thank you!
star-5
Weekend Trip
MyleneAnn_I
, Aug 2020
It is a nice tour. But it was not a 11 hrs trip. If it is 11, we could have spend more hours in the town of Montalcino for example(to enjoy the stunning view). But it was a nice trip. We visited the places indicated. Alex, our driver as well, was so kind. He discussed briefly about the place before we walk around the towns. Too bad, we only have 1 hr on each towns. And mostly we spend the trip on the van. But I think it is worth it! You can try it if you do not have a car.
2 travelers found this review helpful
star-5
Fun day in Tuscany
betsys86
, Oct 2019
Our lovely tour guide was punctual, kind, friendly & full of knowledge. She was also very flexible in stopping the van so we could take pictures!
star-5
A fun day in Tuscany !!
CaroleWashingtonDC
, Oct 2019
This tour was a blast! We had ample free time in the villages we stopped at, the lunch was wonderful and the wines sublime. Seven strangers became quick drinking buddies 😂. I thoroughly enjoyed the day with Daniel as our lovely guide. Highly recommend!!
star-5
Perfect Tour
Dimple L
, Aug 2019
Vincenzo, our tour guide was wonderful. He picked us up early from our hotel and got us to our first stop in San Gimignano before all the tour buses got in. We had over an hour there to visit the beautiful town and even get some delicious gelato from the best gelato place recommended by Vincenzo and do some shopping. We then stooped at our first winery for wine tasting and lunch. Vincenzo drove through some amazing towns with beautiful sceneries, stopping to let us take pictures. We then stopped at another winery for Chianti and Brunello tastings and had more time to ourselves in Montalcino.. Overall a great tour and will definitely recommend!
star-5
Great Experience
Jason P
, Aug 2018
First off our guide was amazing, she picked us up from the hotel right on time. She was very knowledgeable and fun. She gave us time to walk around. The wine tasting was fantastic! The wineries were beautiful. It is easy rides everywhere. You get to see a lot. If you like wine, this is a great tour.
star-5
Dolce vita
mehrdad_e
, Jul 2018
pleasant day , must take this tour if you go to Tuscany , we went to two wine tours and beautiful little towns . our guide was good , stopped few places for pictures . we'll do it again

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