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

Hilltop Towns Val d'Orcia

  • 8 hours

Tour Description

For those who want to explore the Val d'Orcia area, a UNESCO heritage site, and discover its enchanting, hilltop, medieval villages, we recommend visiting two villages, Pienza and Montepulciano. Don't forget to add in a traditional authentic lunch stop. Pienza is a marvelous hilltop village famous for its pecorino (sheep) cheese. It is one of the most romantic villages and definitely not to be missed. Montepulciano is a larger hilltop town, it is home to an exciting wine barrel rolling race if you are lucky to be there at the end of August. This town is the perfect place for lunch. Explore the two towns on your own to discover the beauty of these gems. Customize the day to your group based on your needs and accommodation location.

Additional Info

Pick up location

Directly from your accommodation


8 hours


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

Suggested Itinerary


Pick up at accommodation


Drive through the Val d'Orcia with photo stops and a stop in Pienza


In a family run restaurant in Montepulciano




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.

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.

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!