Tours/Montepulciano/Private Guided Tour of Montepulciano with wine tasting
Viator · Private tour

Private Guided Tour of Montepulciano with wine tasting

4.9(17)Montepulciano1 hour
VIATOR4.8(12)TRIPADVISOR5.0(5)

Description

The Montepulciano tour will allow you to discover one of the most fascinating towns of the area, the so-called “Renaissance pearl” sheltered inside Medieval city walls. We will start our tour on the summit of the town, in the magical Piazza Grande, where we will be able to visit the never-finished Cathedral, see the main Gouvernment Palace, the Palaces Contucci and Tarugi, the beautiful 1500 well, and enjoy a wonderful view over the Val di Chiana and part of the Val d'Orcia. We will then descend the town, following the winding main street, thereby admiring Montepulciano's wonderful palaces and churches along the way. We will learn about its traditions … for example:– did you know that once a year they have a barrel-pushing competition? – , and spot all the movie sets of the town! Last but not least, our tour will take us underground to visit one of the ancient wineries of the town, and taste a glass (or more!) of Nobile wine. IMPORTANT: the tour schedule in the system is 10am and 15pm, but the tour times can be arranged directly with the guide upon request.

Tour Options

Private Guided Tour of Montepulciano with wine tasting

Itinerary

120 min

During the tour we will see the highlights of the town, such as the magnificent Piazza Grande, the Medieval Fortress, and the Church of St Augustine. We will also discover the less known corners, looking for the best Renaissance palaces, and panoramic terraces with a view over two valleys. Our tour will then take us underground to see one of the most ancient wineries of the town, and to taste a glass of Nobile wine.

Highlights

Quick tasting of Nobile wine
Private guided tour

What's included

Included
Quick tasting of Nobile wine
Private guided tour
Not included
Any entrance ticket to museums

Traveller Ratings

4.9
17 reviews
5
16
4
0
3
1
2
0
1
0

Important Information

  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels

Reviews(17)

9
97donovanb
June 19, 2025
A terrific day of exploring.

Chaira was very personable and knowledgeable guide. She shared some very interesting historical events. And she speaks excellent English! We also very much enjoyed exploring the wine cellars at the end of the tour.

Operator response

Thank you very much, Donovan, for your nice review!!! It was lovely meeting you and your family too!

Z
Zaida_C
March 24, 2025
Exploring Montepulciano

My wife and I enjoyed learning about the history of the Montepulciano while tasting some wine along the way. Our guide Chiara was excellent! She was knowledgeable, courteous and fun.

Operator response

Thank you, Zaida, for tour lively review! See you next time :)

G
Gregory_K
October 16, 2024
Chiara Is the Best Tour Guide

Chiara was so knowledgeable and passionate about Montepulciano that it mad the experience more meaningful. She went the extra mile to make our experience very special. Any question we had regarding Montepulciano and surrounding areas she had a wealth of knowledge. She was entertaining, and yet the fact she knew about the history of the area were fascinating her knowledge about the architecture of the buildings, and the people that lived in them in the medieval time total story we won’t forget. We would highly recommend Chiara. She totally made the experience a high-quality tour.

Operator response

Thank you so much, Gregory, for taking time and writing me such nice words! Hope to see you again!

T
Terence_T
October 10, 2024
Best guide ever

Chiara was an excellent guide. Extremely knowledgeable about Montepulciano, the history, and “fun facts.” She is proficient in English and super friendly. I think she is the best guide I’ve ever had in 35 years of traveling!

Operator response

Aww Terence, I am not sure I deserve this kindness, but thank you so much, it's very much appreciated!

E
Elizabeth_M
September 25, 2024
Loved Montepulciano and Chiara

Chiara was amazing! So sweet knowledgeable with perfect English! We loved our guided tour with her! Highly recommend any tour with her!

Operator response

Thank you so much, Elizabeth! I had fun with you and the rest of the group. :)

S
Salvatore_Z
April 18, 2024
Montepulciano waking tour

Average tour compared to others. Didn’t enter any buildings or churches Nice person but could have been more informative. Accommodating do to the steepness of the hills. We could tell she wanted to talk us out of the wine tasting as she started saying we could skip the tasting right from the beginning of the tour. It’s at the bottom of the mountain and there was a bus available to take us back to the top but didn’t really facilitate that, therefor didn’t experience any wine tasting.

2 people found this helpful
Operator response

Dear Salvatore, I must say I am deeply sorry to read your words, because I really did not have the impression that you were not enjoining the tour while doing it. You also gave me a tip at the end of the tour, which is a strange thing to do if you did not enjoy something. I can assure you that I not once tried to talk you out of the wine tasting, which had been booked for you and which I had to cancel last minute (causing issues to the winery schedule) because you decided to finish the tour early, due to the steepness of the hill on our way to the winery and your worries about having to climb the hill back up at the end of the tasting. Because of your decision to stop half way down the hill, we also did not go and visit the last part of the town, so maybe that is why the tour felt incomplete to you, we would have had at least 45 more minutes together. Unfortunately, at the moment in Montepulciano the only church that is always open is located in the area that you decided not to go to, while all the palaces are private buildings, so they are closed to public, and I have never advertised otherwise. Besides, if I informed you that the winery was at the bottom of the hill, it was only because you had told me prior the tour that you had mobility issues, which I could also see myself from the beginning of the tour, and as I care a lot about my clients' health and different needs, I just wanted to make sure you were okay with it. In addition to that I also walked slower than usual, always making sure you were okay. Indeed, your wife was the one who asked to stop the tour, as she could not continue walking. You considered continuing the tour by yourself going to the winery with me and without her, which I would have done with no problems, as I told you, but then decided to end the tour and go back to the hotel with her. Unfortunately Montepulciano, like many other Tuscan towns, is located on the top of a hill, and it can be tricky for some people to move around. I am deeply sorry if my questions and concerns about your well being have come out the wrong way in your eyes. I can assure you that, if your health had allowed you, I would have finished the tour with pleasure, showing you the last part of the town and taking you to the winery, where they were waiting for us. I can also guarantee that I do my job with passion and most of the times I stay longer than expected just to make my client's experience the best possible, and never want them to feel like they are in a rush. For this reason I would like to finish by saying that I am very sorry that you decided to give me a 3-star review, when you were the ones who (for health reasons, of course!) did not give me the chance to properly finish my tour, and I would like to kindly ask to reconsider it.

D
Diane_H
September 25, 2023
Outstanding. Chiara was fantastic.

We were only expecting a wine tasting. But found that we had a guided tour of Montepulciano, a charming city, by a charming guide. So much to learn. A wonderful experience.

1 people found this helpful
Operator response

Thank you so much, Diane! Hope to see you again soon :)

S
Steven_D
September 18, 2023
Incredible

Chiara was amazing and really opened up the city for us. We saw a lot more than expected and hearing about the history of the city was really enjoyable. The wine cellar and wine tasting was a great end to the tour. Chiara is very friendly and accommodating. We highly recommend this tour.

1 people found this helpful
Operator response

Thank you, Steven, for your kind review! It was a pleasure guiding you around!

M
Maddie_C
September 10, 2023
Very friendly and knowledgeable! Great way to experience Montepulciano!!

Chiara was absolutely amazing. So hospitable and welcoming. We hit it off right away. She is a wealth of knowledge and knew everyone in town so it felt like we were celebrities! She takes you to the coolest wine cellar and tasting room in town. Loved learning about the history and walking the whole town with her at a great pace!

1 people found this helpful
Operator response

Thank you, Maddie, I had a great time with you too!

C
Catherine T
June 19, 2023
Excellent tour and wine tasting in Montepulciano

Chiara was our personal guide in Montepulciano and she was by far the best guide we had on our 8 day trip through Tuscany. From the spectacular views from the city walls overlooking the valleys of Val D’Orcia, to the historical and artistic sites of the city of Montepulciano, Chiara was very knowledgeable and personable. The highlight of the visit was the tour of the ancient wine caves beneath the Cantina Ercolani and the wine tasting in their beautiful shop above it. We were impressed by quality of the the wine and their knowledgeable staff and we had several bottles along with a bottle of balsamic vinegar shipped home. I would highly recommend Chiara for any tour in the Sienna region of Tuscany.

Operator response

Thank you, Catherine, for your lovely words!

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