Montepulciano, Pienza, Montalcino Tour

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Discover Montepulciano, Pienza and Montalcino on a Private Tour

The central Tuscan area features three of the most popular cities in the region, and among them, you can enjoy some of the best wine production anywhere in the country. The good news is that these three cities are so close to each other that you can visit them all in one day by taking a Montepulciano, Pienza, Montalcino day tour from Florence or Siena, or, better yet, over three days and stay in a central location such as Florence overnight. There are three amazing locals that you can easily tour from Florence or Siena that are not the run of the mill tourist traps your normally get when visiting the Tuscany region.

Chauffeured Tour to Enjoy Montepulciano, Pienza and Montalcino


Located 50 km southeast of Siena, it can be reached from Florence in about 1.5 hours and is only 40 minutes from Siena. It is located in the Val d’Orcia, a part of Tuscany with some of the most unique and attractive landscapes, and perhaps one of the most iconic, when one thinks of the region. The popularity of the area, as well as its stunning beauty, is one of the reasons that specialized Tuscany tours never omit it from their itineraries. Montepulciano is synonymous with great wine and Renaissance beauty, its nickname “little Florence of the countryside” eloquently describes the beauty and value of this town. It consistently appears in TV ads and is often used as the set for blockbuster movies such as “Under the Tuscan Sun” and “The Godfather”. Montepulciano, a perfect Tuscan hill town, boasts the oldest registered wine of Italy. While you are in the town, make sure that you try a glass, it is an experience unlike any other.

The main square of Montepulciano with its palaces and monuments is considered a jewel, and even more impressive is the temple of San Biagio, the finest early Renaissance architecture gem by Antonio Da Sangallo Il Vecchio you may find in Tuscany. Another interesting factor is that you can take a unique tour underneath the beautiful Renaissance palazzos.

The historical aging wine cellars that were famous already at the time of Lorenzo the Magnificent, have been the home to wine that is considered to be among the best in the world for as long as the town has stood. The wine produced here is called Nobile (i.e. noble) a tradition that has lasted for over 8 centuries, and which dates back to the times when the wine that was made here was reserved for the uppermost echelons of nobility in Italy. They demanded the best of everything, and when it comes to wine, arguably that is the wine produced in Montepulciano. Needless to say that wine is the main character in this area, we have selected 11 wineries where we can take guests for wine tasting tours and winery visits. For more information, please speak with your driver guide, or with the agent who books your package, and they will be happy to help you select the best ones to visit according to your tastes.


Located 40 km south of Siena, it can be reached on a Siena or Florence wine tour in about 1,5 hours and only 30 minutes from Siena. The tour will take you through this beautiful countryside of Tuscany. The town was once part of the state of Siena, and the unique qualities of its culture are still clear. While visiting this incredible town, you will have the chance to also visit the small city center. The city center is one of the oldest and most well-preserved of the small town squares of medieval Italy. The stunning architectural work is a must-see, and the artistic expression of the entire square is without rivals.

Your tour ends at the impressive 14th-century fortress that was once used by the people of Montalcino and those of greater Siena to defend themselves during times of besiegement. Make sure that you don’t miss the chance to climb its ramparts to feast your eyes upon one of the best views of the Tuscan region in all of the area. From the high vantage point, the landscape of Tuscany stretched out in all directions. Once you are done admiring the view head down to the wine cellar for a one-of-a-kind tasting opportunity. The tasting offered by the enoteca located in the cellars of the fortress offers the chance to taste what is among the best traditional DOCG red wines of Tuscany.


If you are a lover of cheese, and let’s face it, who isn’t, then without a doubt this is the perfect place for you to not only learn about but taste one of the world’s most popular Italian cheeses, Pecorino. Pienza is also located in the Val d’Orcia. It is a wonderful small hill-town which was entirely redesigned in the 15th century to become the “ideal town” by Renaissance man and Great Pope Pius the II who commissioned the project to the architect Rossellino. In the countryside surrounding the town, there are various dairy farms renowned for the finest pecorino cheese. We may include a visit to one of this farms to see how the production and the aging take place if there is time left during the tour booking. Naturally, a lunch on the premises might also be included so as to also enjoy the locally produced cold cuts and, of course, that amazing cheese.

These simple day tour options from Florence or Siena offer you a glimpse into the real Italy, not the packaged Italy that you see on TV or get form major tour. These three locals make taking the time to visit them from Florence or Siena well worth it.

What our customers are saying


I want to thank you for such a wonderful vacation that my family had with your company. Our trip to Italy was one of the best we have experienced. That greatness was made in large part by the people that looked after us and toured us from place to place. I hope to travel with you again when we come back to Italy!

Jennifer L.


I just wanted to say thank you for all of your help coordinating our travel throughout our stay. We absolutely loved each of our drivers and everything was truly perfect. We will sing your praises to any and all friends who may be traveling to Italy and I hope to use your service when we can make it back there ourselves!

Anna F.


I was extremely satisfied with all aspects of our journeys from Florence to Siena and from Siena to Rome. The drivers and cars were excellent, the timing perfect and I would have no hesitation in continuing to book with you in future. Thank you for all the help with our transportation needs. Your team is so great!

Andrew D.


We had a wonderful day trip with our Driver Guide! He was polite, intelligent, considerate and extremely knowledgeable! We appreciate every consideration he showed to make our experience in Tuscany beyond our expectations. We will definitely recommend your company to our friends and use you again in future!

David B.


I just wanted to say that our driver was absolutely exceptional!! Friendly, extremely safe, efficient, punctual and very accommodating... just above and beyond in every way. He had great recommendations too (restaurants, wineries, shopping, etc) We will 100% use your services again, and highly recommend you to our friends.

Samantha C.


Our transfers from airport and all other transfers were perfect. All of the drivers we had were absolutely brilliant, attentive and welcoming as well as being on time in every case. Thank you very much for making our holiday stress-free and enjoyable. Your company is just great, and we had terrific experiences!

Phil M.