VIP Chianti, Brunello wine & Pienza with lunch From Siena

Recommended by 100% of travelers

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Siena, Italy

8 to 9 hours (approx.)
Mobile ticket
Offered in: English

Overview

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at wineries in the Chianti hills and Montalcino on this small-group tour from Siena. All of your transport is included for a hassle-free experience, and there's even free time to explore Pienza on your own. Sample top Chianti and Brunello wine at two boutique wineries, and relax over a Tuscan lunch.

A small-group tour (6 people or fewer) ensures an intimate experience
Visit two boutique wineries for tastings and lunch
Round-trip transfers are included for a seamless experience
Explore the town of Pienza at your own pace

What's Included

Brunello di Montalcino, Super tuscans, Chianti Classico & Rosè wines
Small group max 6 people
Alcoholic Beverages

2 wineries including Chianti Classico & Brunello di Montalcino
Lunch

Homemade pasta, Pecorino Cheese, ham, salame and bruschetta.
Tour of 2 wineries historical cellars
Licensed tour guide
Organic Balsamic vinegar & Extra virgin Olive oil tastings

Museums tickets

Meeting and Pickup

Meeting point

Prosperino Bistrot
Viale XXV Aprile, 53100 Siena SI, Italy
OUTSIDE PROSPERINO BISTROT. THE GUIDE WILL BE WAITING OUTSIDE ON THE TERRACE, NEXT TO THE OLIVE TREE STATUE.

End point

This activity ends back at the meeting point.

Operating hours
.10:30 am

Itinerary

Siena

30 minutes • Admission Ticket Free

Castellina In Chianti

2 hours • Admission Ticket Free

Montalcino

1 hour • Admission Ticket Free

Val D'Orcia (Pass By)

Pienza

1 hour • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Stroller accessible
Service animals allowed
Near public transportation
Not recommended for travelers with back problems

Not recommended for pregnant travelers
No heart problems or other serious medical conditions
Travelers should have a moderate physical fitness level
This tour has been upgraded for 2025 so the reviews may be different from description.
This tour/activity will have a maximum of 6 travelers

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Cancellation Policy

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

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Michelle_M

An absolutely perfect day! Morad was super knowledgeable and friendly and we had the best experience. Both wineries we went to were amazing as well as the other 2 stops where we got to walk around. Highly recommend this tour it exceeded my expectations!

Reviews

5.0

based on 28 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Wonderful Tour

joann_r, Sep 2025

Our tour guide was Marado and he was wonderful. He pointed out interesting things along the way, also showed us wonderful spots for scenic pictures.

Response from Host, Jan 2026

We really appreciate your review! Knowing that you had a memorable experience in Tuscany makes our day. We strive to offer authentic and enjoyable tours, and your comments encourage us to keep doing our best.

Amazing Experience

Michelle_M, Apr 2025

Response from Host, Jan 2026

Thank you for your kind words! We’re thrilled you enjoyed your tour in Tuscany. Sharing the beauty, history, and flavors of this region is our passion, and we’re so happy it made your experience special.

An exceptional Tour

Alan_G, Sep 2023

An exceptional tour with our exceptional guide Moro! We contacted Moro in advance of our planned tour to customize our tour a little bit. He was accommodating and created a plan that worked perfectly. We replaced the Wine Tour part because we had this planned elsewhere. We still did the Siena Underground & San Gimignano portions. These places were absolutely wonderful. In Siena we had the best pizza & gelato during our trip. Thank you for the recommendations Moro ;) including the dinner recommendation too! Moro was a wonderful guide and a pleasure to spend our day with. Pickup and drop off were easy as was the whole day. I encourage you to make this a part of your plan during your stay in Florence, you'll be very happy you did.

Response from Host, Jan 2024

Hello Alan, Thank you for the great feedback. We also do our best to satisfy travelers needs :)

Great, varied day out

Sarah_M, Sep 2023

Easy communication and pick up for a lovely in Tuscany. Although very busy in Siena & San Gimignano, still worth a day as beautiful. The wine tasting was very good in a beautiful winery. Moro, our guide and driver was very knowledgeable and efficient. The vehicle was not a van but a car with a small bench seat as a 3rd row. My husband in the front, 2 sisters in the middle and me in the back. It was a bit limited for leg room and a bit bumpy but I did chose to give the others more room. The drive is long, based on volume. All that said, I would recommend

Response from Host, Sep 2023

Hello Sarah, Thank you very much for the wonderful review. I wish you all the best and hope to see you again in Tuscany :)

A Great Day in Tuscan Country

Robert_F, Aug 2023

We signed up for this because I was trying to avoid an all-day coach bus tour but wanted to see the area and go to a winery on our family trip to Italy. Morad met us at a beautiful Piazza, and we walked a few minutes to the train station where he was parked. The car was a nice seven seat SUV which is why he limits the tour to no more than six (the sixth person will have to ride in the middle of the second seat). We were lucky to have five so everyone could easily see the pretty car ride. Morad was a great driver and we headed to Siena, his hometown. Our first stop was a wine shop, whose owner had discovered an ancient cave (Etruscan tomb?) while renovating the back of his store (thus the "underground Siena"). It was a cool experience to visit, and it is where the owner hosts wine tastings now. After that Morad hit a few highlights of the medieval city and the banking history it had also. He then gave us a few minutes free time to check out the sites and shops before we had our included lunch at a nice restaurant not for from the city center. On our way back to the car, we stopped at the wine shop for a bonus tasting and learned about Brunello wines. The shop has a popular wine club if you want to order some. From there we went to the local winery Lornano to learn about how the different wines are made and have a tasting. While there is no hard sale at the winery, when I have my wife and three daughters telling me how much they liked the wine, I did order a case. I am willing to pay a premium not to have sulphates in my wine. Our last stop was the medieval city of San Gimignano, where after waiting in line for the world champion gelato, we were limited on time to see. However, I was happy to be back to Florence by 6:00 (9 hours total). Morad is a great tour host, and the private tour was well worth every penny. Book early for this tour group because they will sell out.

Response from Host, Aug 2023

Dear Robert, Thank you for taking the time to write such a wonderful review. We are glad you loved it.

Beautiful day in Tuscany

Richard_Y, May 2023

This was a wonderful tour through Tuscany. There was only one other couple in our group and our tour guide was great, giving us more time in places we really were interested in seeing. Great food, great wine and beautiful country side.

Response from Host, Aug 2023

Hello Richard, We are very happy to hear about your feedback. We hope to see you again in Tuscany ;)

Wonderful time in Tuscany!

sidnevaldivieso, Mar 2023

We had a wonderful time with Morad! He knew so much about everywhere we went. He gave us plenty of time to look around on our own, too. He even dropped us off closer to our hotel since it was on his way! The wine tastings were lovely, as was lunch in Siena.

Response from Host, Aug 2023

We are proud to read this amazing review. Thank's ;)

A must do tour

Alicia_J, Mar 2023

The guide, Morad, was great! He was very knowledgeable of the area and history. This tour was preferable to others because it was 6 people or less which is hard to find leaving out of Florence. We really enjoyed the more intimate and unique experience we had of Tuscany. I highly recommend doing this tour!

Response from Host, Aug 2023

Thank you Alicia :))

Pure Magic

Adele_P, Jan 2023

There are no words that can adequately explain the pure magic of this tour! Morad, our guide, brought his intimate knowledge of the area along with his wonderful personality to give us unforgettable memories. The tour had to be amended slightly due to water issues but Morad provided an additional stop that was breathtaking. The tours are limited in size making the day more personalized and relaxed. The winery stop was very exclusive, allowing us time to enjoy the high quality wines and tasty snacks. We will absolutely reserve other tours with Morad when we return to the area. Do not hesitate to book and experience a unique tour of exceptional quality.

Response from Host, Feb 2023

Probably the most beautiful review we have ever received. Thank you very much Adele, we really appreciate it the time you took to write this wonderful feedback.

Highly recommended

travel, Dec 2022

It was a great tour with a very professional guide/company - we would highly recommend it thank you so much !

Response from Host, Feb 2023

Thank you very much for the time to leave a review. We are always happy to see wonderful feedbacks.

Tuscan Adventure

Bruce_A, Sep 2021

Best day of our trip outside Florence. The owner and guide Morad was excellent. Extremely knowledgeable and fantastic personality. Gave complete history of Siena and San Gimignano on our beautiful ride through Tuscany. Wonderful experience, would highly recommend!!

Response from Host, Sep 2021

Thank you very much Bruce for the great feedback. I really enjoyed having you in tour with me, was really fun. Hope you enjoyed the rest of your vacation in Italy. Arrivederci

Likely to Sell Out