Montepulciano in 24 Hours

Updated: Jul 18, 2021

Everyone dreams of visiting the beautiful vineyards of Italy, but it is not always known that they are difficult to get to if you don't know what you're doing. Montepulciano is a small town hidden in the vineyards of Siena—the red wine country. There's so much beauty to be explored, so let's dive in to your Montepulciano travel guide.


How do I get there?


Though most of Europe is accessible by train, Italy still has a number of towns that are tricky to get to. While you can take a train from Florence or Rome into Siena, you would still have to take a bus or drive into Montepulciano. With that said, my recommended mode of transportation is to rent a car.


It's just over an hour and a half car ride from Florence, and the Florence airport has several rental car options to choose from. Plus, the vineyard views you'll pass on the way into the town are truly indescribable—it's worth the drive. If you're coming from Rome, it's about a three hour drive.



Where are the best places to eat & drink?

  • Villa Sant'Anna - This was by far one of our favorite stops in the whole country. The couple days we spent in Montepulciano were rather rainy, but fortunately, that meant we were some of few people going to vineyards. We had a private tour of Simona's vineyard (Villa Sant'Anna), and we practically spent the entire day with her drinking wines, eating cheese and talking about how she started the vineyard with the help from her daughters.

  • Locanda Cicolina - Another must-do, Locando Cicolina is a fabulous, small restaurant that overlooks the beautiful country-side hills. Everything on the menu is made from scratch, and the wine, of course, is all from the region. You can't go wrong by ordering anything here.

  • Trattoria di Cagnano - Though there are several small Osteria and Trattoria in the town's center, Trattoria di Cagnano happened to be one of the restaurants we stumbled upon and quite enjoyed—I recommend asking for the outdoor seating.


What are some fun things to do near by?

  • Montepulciano - Just walking along the center of the town, you'll find so many cute shops, wineries, olive oil shops and more. The town's church, St. Agostino, is also a beautiful site along the street lined with vendors. There are also other small towns nearby like Pienza that are in driving distance.

  • San Gimignano - Also in the region of Italy, San Gimignano is about an hour and a half drive north (closer to Florence) from Montepulciano, with a similar town structure. Though, San Gimignano has what is said to have some of the best gelato in the world—Gelateria Dondoli.

  • Perugia - Only about an hour drive from Montepulciano, Perugia is known for their chocolate more so than their wine, but altogether, a great addition to the Italian journey.


Where are the best places to stay?


  • Villa Cicolina - Yes, the same restaurant I recommended earlier also has a beautiful villa! If this one is full, don't worry, there are plenty of beautiful villas nearby you can stay at.

  • AirBnb - For a more affordable option, there are several AirBnb listings throughout the town, this was the one I last stayed at. It was beautiful, conveniently located and included parking—this was definitely the best "bang for our buck" stay.



God created such a beautiful world, it would be a shame not to explore, preserve + appreciate it.


Explore: the inner-city of Montepulciano. Many of these streets are ancient, and there's so much beauty to be found even within the walls of the town.

Preserve: the vineyards. Good wine does not make itself, so we have to respect where it comes from. Temperature increases, precipitation pattern changes, extreme weather and water availability can all affect agricultural productivity. With issues like climate change, any type of farming is at risk, so it's important that we take our actions into consideration.

Appreciate: the breath-taking views of the hills and valleys of Italy's wine country.


Have you been to Montepulciano? Share your experiences below!



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Hi, I'm Anna!

Whether I'm flying confirmed or standby, I've always had this affinity (and knack) for packing in as much as possible in 24, 48 and 72-hour trips. And that's exactly what this blog is full of—quick trip travel guides!

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