Cities, Cheese and Wine Tour in Pienza & Montepulciano

We had an absolutely wonderful day with Michele exploring Montepulciano, Pienza, and enjoying a beautiful cheese tasting in between. From the moment we met him, it was clear we were in incredibly capable hands. Michele’s knowledge is outstanding — our car rides between stops were filled with fascinating stories, history, and insights that brought the entire region to life. We learned so much more than we ever would have on our own. What really set Michele apart was how thoughtfully he accommodated our small family, including our 3-year-old. He was patient, flexible, and made sure our little one was comfortable and included throughout the day — no small feat on a full day tour! He was friendly, attentive, and punctual at every single stop. If you’re visiting Tuscany and want a guide who combines deep local knowledge with genuine warmth and professionalism, look no further than Michele. We cannot recommend him highly enough — one of the highlights of our entire trip to Italy!

We have actually booked 5 days of tours with this Company. Our driver for two of the days was Camilla and she was an excellent driver giving us history lessons and some basic Italian lessons. Today we did an EVOO tasting in the morning, a sheep farm, where they make wonderful cheeses and serve a delicious lunch, afterwards. On the way back to our hotel in Florence we stopped in Pienza for breathtaking views of the walled city. I highly recommend this Company for a fun filled vacation where everything is taken care of for you and you only have to ride in the van. Definitely an enjoyable experience!

If you want a relaxing but varied holiday in beautiful Tuscany based on a farm with modern facilities and a pool with cooking classes and visits to local towns, this is the right holiday for you. Up to 12 people can stay for either one or two weeks with most meals included. Chauffeur- driven cars with friendly drivers took us to Cortona for dinner at a different restaurant every night and classes in cheesemaking and pasta-making were included. The hostess organised transport and the daily activities into which we had input, especially when there was free time.

Niccolo and his team at Tours of Tuscany made our large group experience in Tuscany an unparalleled luxurious once in a lifetime trip. When I stumbled upon this company online a year before our trip, I had no idea that it was the best decision I would ever make in planning a week long vacation for our group of 11 friends and family. This local company pulled out all the stops, beginning with a consultation via video chat six months before the trip and recommending ideas based on the interests of our group. They personalized the tours for us and made our vacation truly stress-free. They arranged for two Mercedes minivans to transport us safely through the countryside, with drivers who were friendly, accommodating and generous with providing recommendations and insights into local life and points of interest. Everyone felt safe and well cared for. Each experience was thoughtfully planned and executed perfectly. They took us to places we wouldn't have found on our own and with VIP treatment. The cheese farm lunch and tour was a highlight of our day traveling in the Val d'Orcia, then the adorable towns of Pienza and Montepulciano.

Stefan was a wonderful guide and was very knowledgeable about wine. Both Vinyards we visited were hosted by very friendly owners The tastings at both were excellent in beautiful rooms and cellars. Views of Tuscany going and coming were fantastic. The lunch in Pienza on a beautiful day was outside on a patio with a gorgeous view. 3 course lunch was very good and a super Tuscan bottle for the table. Of course I bought some Pecorino cheese while there. Tasting Vino Nobile and Brunella in the same day was a dream come true.

Stephan was an amazing guide and driver for our day. He knowledge about the region made our day fun and informative. We would highly recommend this tour and exploring the hidden gems.

I went with my mom and we had a great experience. She has a hard time walking and she was able to manage it well. The two wineries we went to were architecturally amazing! Both very different and very unique in their own way. The wine was delicious. The guide was great and provided us with lots of information on the area and the history of the vineyards and people that lived in the area.

Niccolo provided us with an amazing tour around Montalcino to incredible wineries. He was very knowledgeable of the history with Tuscan winemaking and spoke amazing English! We learned the history of the winemaking from both the beautiful wineries we went to and enjoyed an incredible 3 course lunch with wine. We highly recommend Niccolo and Alexandra’s services!

Professional people where they take you to the best places to enjoy a phenomenal day. Dream places where you can also enjoy a good wine, a good cheese and a delicious ice cream. Thank you Niccolò.

This has been the best tour I've ever done in my entire life. Niccolò and the guide have been phenomenal, professional, detailed giving also a fun touch to the whole tour. I have taken advantage of all the wine and cheese tastings with my partner (goodness the pecorino, made with sheep milk) and the wonderful panoramas they have shown us. I fell absolutely in love with Pienza. The next trip in Tuscany, I will not hesitate to call again the Tours of Tuscany. It was one of our best experiences!!