The Ideal Day Trip in the Tranquil Tuscan Countryside

day trip from rome to montepulciano and pienza

This trip to Montepulciano and Pienza, complete with lunch and wine tasting, is the perfect get-away.

Are you looking for a break from the hustle and bustle of the city of Rome? Or an easy-to-plan day trip while vacationing in Italy? This excursion to Tuscany is the perfect medley of sightseeing and relaxation. Aside from the amazing aesthetic and picture-perfect setting offered by the small towns of Tuscany, this day trip includes fabulous Tuscan cuisine and the best tasting wines

I had the privilege of attending this guided trip to Tuscany and I could not have been more pleased with my experience. The trip includes four stops in Tuscany, one of which is a lunch and wine tasting. It is important to do your research before booking trips and tours like these, so here is everything you can expect for a day in Tuscany.

Sites visited

  • Montepulciano
  • Lunch and wine tasting
  • San Biagio church
  • Pienza


You begin in the Piazza del Popolo, an easily accessible spot in the middle of Rome. Here, you can quickly spot your tour guide.

The bus holds about fifty people, yet the ride was extremely comfortable and not at all crammed. While you may begin this trip as a group of strangers, after a day together (and some wine) you are sure to leave this tour with some new friends.

My group’s tour guide facilitated a lovely and comfortable environment for everyone. She was ready to assist the group with any concerns that arose. The bus ride is about two and a half hours. The bus will stop mid-way through its trip for the use of a bathroom and the opportunity to grab something to eat at a cafe, so there is no need to bring snacks and anything extra you do choose to bring you may leave on your seat on the bus while touring Tuscany. 

Guided tour through Montepulciano

The first stop is the small and dreamy town of Montepulciano. Initially stepping off the bus I was greeted with the sweet-smelling Tuscan air and the vast green landscape of the countryside.

Montepulciano is a town built in the medieval times, its oldest building dating back to 1210. The town sits on a hill that is 600 meters in elevation, therefore it provides gorgeous panoramic views of Tuscany. With the town being on a hill, there comes some very steep streets. If you are not able to handle this type of terrain you are welcome to hang out at the bottom of the hill where there is a small café with a great view while the rest of the group goes on a guided tour.

You are provided with a headset so you can clearly hear the voice of your tour guide no matter your location in the pack as you learn about the enchanting history of the town.

After the tour there is some free time to explore all that Montepulciano has to offer. I recommend looking in the jewelry stores as the town is historically famous for its jewelry production. The shopping does not end there as Montepulciano presents a medley of all the quality products sourced from the Tuscan region. The straw hats sold around the town is a commodity that originated in the Middle Ages and is made from the wheat grown in the area.

Along with that is Tuscany’s famous Umbrian chocolate and lots of other unique spots and shops. In Café Poliziano you can sit down and enjoy a coffee in the exact spot where Medieval nobles used to do the same and in the boutique of Porta della Cavina, you can witness a Tuscan tomb, free of charge. 

Lunch and wine tasting

Next you are transported to a family restaurant owned by two sisters who are dedicated to keeping their family recipes alive. The meals that they serve you are the same they ate growing up in their family’s kitchen. Therefore, to share their cuisine with their guests is an absolute honor. For the time you are dining, you are treated just like family. Not only is the atmosphere homely, but the food is delicious.

You will have the pleasure of indulging in three courses of traditional Tuscan cuisine and taste the best wines of the area. The sisters will even show you their wine cellar where they age their in-house wines. During the lunch a white wine, a rosé, and three red wines are served. The last red is of course the most anticipated, the famous Tuscan Brunello

Stop at Chiesa di San Biagio

The Church of Saint Biagio is an astonishing piece of architecture with equally awesome views. The trip does not include an entry to the church, so if you would like to go in it is an additional fee. However, the beauty of its outer walls and the surrounding landscapes are certainly enough. It is the perfect opportunity for some pictures or to simply breath and soak up the scenery. 

Meander through Pienza

Day trip to Tuscany lunch and winetasting

The last stop on this tour is the little town of Pienza. Strolling through the alleys of this town felt like walking through a scene of a movie. Like Montepulciano it is elevated, but the terrain is much flatter. Here you can walk the streets along the edge of the hill and again admire the charming countryside. 

The Cathedral of Pienza is a gorgeous catholic church that is free of charge to enter. Its architecture contains gothic and renaissance elements. The town also contains many small shops you are more than welcome to explore. One gelateria is famous for its pecorino flavor. If you are curious as to what that could taste like-I was too. After sampling I was pleasantly surprised, in my opinion it resembled the taste of whipped cream, but you will have to judge for yourself. 

Why you should book this tour

After Pienza it was time to return home. You are bussed back to the same piazza you left from. I left feeling completely content with my experience in Tuscany. The day was a perfect combination of being a tourist and being on vacation.

I got to learn so much of the history of Tuscany, experience its authentic cuisine, and try the best of its wines. At the same time the ambiance of the countryside and the gorgeous scenery was the perfect catalyst to unwind and relax. I felt completely taken care of in the hands of the tour guides, driver, chefs, and other staff.

The trip was well organized, and the employees generated a positive environment. There is so much more to be said about this trip and Tuscany, but you will just have to experience it for yourself. Enjoy your time in Tuscany!

Meeting point:
Piazza del Popolo

13 hours

Starting time:

Cost p.p.:

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