• Via della Sapienza, 14 Siena
  • +39 3336219136
  • info@wedriveyou.it

Montalcino Brunello wine, Val d’Orcia Unesco & Pienza Unesco sites

  • 8-10 hours

Tour Description

Do you love your wine but don't want to miss the Val d'Orcia? Why not spend a day doing both? Start the day out in Montalcino and enjoy a Brunello tasting in a couple of boutique, off the beaten track wineries. After lunch, move on to visit Pienza and enjoy the amazing scenery of the Val d’Orcia, a UNESCO heritage site. As a lunch stop we normally recommend a family run place where you can do a Pecorino (sheep) cheese and olive oil tasting, and where all the ingredients come directly from local farmers.

Additional Info

Pick up location

Directly from your accommodation


8-10 hours


In a unique location with typical, local far, excluded from quotes

Suggested Itinerary


Pick up at accommodation


Montalcino with a couple of tastings in family run, boutique wineries


Organic, family run estate with local produce. Part of the lunch experience is a Pecorino (sheep) cheese and olive oil tasting


Visit Pienza and then enjoy a panoramic drive through the Val d’Orcia


Drop off at accommodation


Michael V ( Jersey City, New Jersey):

TOUR: Pienza, Montalcino, vino Brunello e formaggio pecorino simply amazing!!!
After weeks of research we finally decided on this tour. We knew we did not want a large group tour as the reviews looked largely terrible. We also wanted a Brunello wine tasting experience (vs Chianti) — which if you know your Italian wines — you know Brunello is the king of Tuscany. This tour had everything we wanted on paper but no reviews — so we decided to take a chance and it was by far the best experience of our 2 week Italy holiday from NYC and that was against tough competition including Milan, Florence, Cinque Terre, and Portofino!
Words can barely capture this experience but here is my best attempt as we want everyone we know to book this tour. It was that memorable!
Our driver, Dario, picked us up promptly at the agreed upon time at our hotel in a brand new Mercedes Benz E-class and drove us 1.5hrs to the Brunello / Montalcino wine region. Dario, recently certified as a sommelier, gave us a tremendous overview of Italian wine as well as a history lesson of the region (Tuscany, Sienna, Montalcino, etc.). My wife and I fell in love with Dario’s blend of tremendous knowledge and warm personality. He was simply amazing and we gained a friend for life.
The tour itself was simply amazing and included; - 1hr stop in the charming Medieval town of Pienza where we bought amazing blocks of Pecorino cheese and walked around the quaint Medieval town.
- 4-course lunch at a 1000 year old Tuscan farmhouse. The host family was so warm and welcoming. They gave us a tour of the farmhouse and then we had lunch with ingredients all sourced from their garden / farm in front of a 500-year old olive tree. Their homemade olive oil was out of this world and we bought several bottles to bring back to NYC. The food was simply amazing; easily best meal in our 2 weeks in Italy.

- Brunello tasting at two amazing family owned wineries. The tastings included: Rosso, Brunello, Brunello Reserva, and Grappa (digestivo). All were amazing! Again, the host families for each winery welcomed us as if we were family
- getting to know us before starting the tour and tasting.
We bought a case from each winery and can’t wait for them to arrive.
The 2012 Brunello’s were simply amazing. 👌

We thought the personal touch this tour provided was invaluable and easily money well spent.
We would have paid 5x what we paid.

If you want the most memorable Tuscany tour of your life, we highly recommend this tour!
We can’t recommend this tour enough.

Jacqueline P:

My husband and I had Tomas' services for a day, exploring the Val D'Orcia beautiful side of Tuscany. Tomas was very prompt with responding to my messages, and suggested a great itinerary based on our personal preferences. We were based in Florence, and this was not a problem for him (as it was for some other private services I contacted to get quotes). He picked us up at our Airbnb rental in Florence, and we headed out for a full day of exploring the beautiful and unique scenery and wine country. Tomas stops wherever we want for photos, and is very happy to take multiple shots until the desired outcome. :) He was such a pleasure to share our day with! He picked beautiful and quality Brunello & Rosso di Montalcino wineries, and a scenic restaurant with fantastic views. He definitely understands your own desires and will tailor the itinerary to your liking, with his expert suggestions. He speaks perfect English and Portuguese - I am a Brazilian living in the US, and he switched into Portuguese as soon as he found out! :) We can't wait to go back to Tuscany and hire his company again! We found a friend in Tomas, and we hope everyone understands how great of a service he provides, and hires him and his team for private car needs while exploring Italy.

Ray E.:

“Beyond the call of duty”
This was not this exact tour, but even better. My wife and I were in Cortona on a 12 day Italy tour. We love Brunello's and had a tasting already set up. We thought about driving ourselves, and we are GLAD we didn't! Tomas knew the roads like "the back of his hand". We didn't have to find a way to Siena, as he picked us up at our villa in Cortona. He worked around our 300pm tasting with a tasting at Podere Le Ripi, a small organic winery exploring new techniques and a Fabulous lunch at Trattoria Leccio. Excellent English skills and even a better personality. Would travel with him again.

W. Johanna (Peoria, Arizona):

This was the most memorable experiences my husband and I will ever have! Being older we decided not to rent a car but instead find a small local company to be our tour guide in Tuscany. Tomas' company had been recommended and he was a pleasure to work with. We exchanged many emails discussing what we liked to do and see and then he planned 3 wonderful day tours that exceeded our expectations. Roberto was our guide and words cannot describe what a pleasure it was to spend 3 days with him. He is locally born, has a wealth of knowledge and became a great friend. We learned more about Italy, its culture and history, than we ever imagined. We tasted Brunello wine at a lovely small winery, more wine and honey at an organic farm, and had one of the finest meals ever at a beautiful organic farm. We visited wonderful towns, ate at lovely restaurants (which Roberto always arranged) and saw museums and churches that many people never have to the opportunity to see. Roberto makes sure everything is done leisurely and at your pace and transportation is in a comfortable Mercedes with door to door service. We've visited Italy many times but after spending time with Roberto I feel like I've seen a brand new country. Italy is lucky to have such a wonderful person as Roberto.

Diane Bertrand:

TOUR: Montalcino
Roberto was friendly, informative, and very knowledgeable about the area. He arranged a lovely lunch at an agriturismo for us and was flexible regarding the itinerary. The car was very comfortable and his driving was excellent. We are very glad we booked this tour and, as a result, felt we knew Siena and Tuscany much better than we would have otherwise.

Lexie S.:

Traveling to a foreign country is a rewarding experience, but it can also be a little overwhelming to plan. Most savvy travelers can figure out the popular sites to see, but the biggest challenges are the logistics of how to get to places and how to find the hidden gems off the beaten path. Sure, you can read tips from travel books or blogs online, but your best bet is to hire Tomas. As your personal driver in Tuscany, you can be rest assured that not only will everything be taken care of, but you will have the most memorable experience during your visit.
The Good: As a local to Siena, Tomas knows Tuscany inside and out. He took the time to understand the purpose of my visit and what I wanted out of my tour. He designed my tour based on my personal interests. This is not a "one size fits all", cookie cutter kind of tour... he coordinates the tour to make sure you get exactly what you want. We drove along the picturesque Laurentana Road and visited the abbey of Monte Oliveto which had frescos from 1444 ad, ancient library and medieval pharmacy. Then we went wine tasting in Montalcino, stopped for lunch, and checked out the quaint town of Pienza where I sampled delicious pecorino cheese.
The Bad: My limited funds. :) If I could, I would hire Tomas for a whole week! Alas, I could only afford him for an afternoon tour. The great thing is that you have a choice to either go for 4 hours or 8 hours. I originally signed up for 4, but once we got out there, I wanted more! Luckily for me, Tomas was available and my tour was extended.
The Unbelievable: Tuscany is absolutely gorgeous, and there is so much to see. Where a tour with Tomas differs from the others is that he explains mostly everything you need to know while you're driving. Unlike typical bus tours, he's able to stop along the way so that you can take photos. We stopped at least 10 times to capture some majestic views straight out of a postcard/calendar/movie! Not only is Tomas friendly, he is extremely knowledgable and professional. Once you get to your location, you are free to roam on your own... Soaking up the beauty of Tuscany and experiencing the joy of Italy as it is meant to be! No head phones or annoying "follow the flag" guides.... with Tomas, you get to experience Tuscany as a sophisticated traveler and you return from this tour truly enriched with the treasures of the area. I highly recommend taking a tour with Tomas!
PS: I am staying in Italy for a month. Siena is my home base while I'm taking classes, but on the weekends I made plans to travel to nearby cities. I had a problem with transportation when a bus left my class on the side of small country road near Montepulciano. That evening, I was supposed to take the train to Rome. When I saw that my original plan was starting to fall apart, I called Tomas. He truly came to my rescue!!! He made a special arrangement to find me in Montepulciano and he ended up driving me all the way to Rome. (I even got an Italian lesson on the way.) Tomas has become more than a tour guide and a personal driver for me. He's like that friend you can call upon when traveling abroad! Thank you, Tomas!