Montepulciano Travel Guide

Montepulciano

Craig and I just got back from a whirlwind 2 week trip to Italy and by far the standout for me was our time spent in Tuscany. This was both of our second trip to Italy; however, while Craig had been to Tuscany on his first trip, I hadn’t. So this was my first time experiencing the magic of Tuscany. 

Our first stop in this enchanting region was the charming town of Montepulciano. This was one of my FAVORITE places we visited.

Cugusi Silvana for an unforgettable picnic lunch

Before we headed into the historic center, we made a stop for lunch at the cutest farm for a picnic lunch, Cugusi Silvana. This is less than a 10 minute drive from the town of Montepulciano and totally worth a stop! It’s a sheep farm that doubles as a B&B and cheese shop. Here you can curate your own picnic basket with the farm’s own cheeses, local meats, jams, bread, and beverages of choice. They have the most picturesque picnic area on the grounds for you to enjoy your lunch overlooking the town of Montepulciano and the Tuscan hills. This was honestly one of the highlights of the entire trip for me.

Commune di Montepulciano for panoramic views

After our delicious lunch, we made our way over to the town of Montepulciano, where we had a 3pm reservation for a cave winery tour at De’ Ricci Cantine Storiche. But first we had to find parking and climb up to the main square of the town…and when I say up, I mean UP! We parked in the P6 lot which was €1.50/hour. We got there before 3pm so we had time to explore the town and climb up the bell tower at Commune di Montepulciano (for any Twilight fans, this is where they filmed part of New Moon). The view from the bell tower can’t be beat! It is spectacular. It was $5/person and has an elevator to take you about half way up, but there are about 75 very narrow stairs to get to the tower view.

De’ Ricci Cantine Storiche for a unique cave wine tour

We made our way down from the tower and meandered our way down the road to De’ Ricci for our wine tour. We called them on our drive to Montepulciano earlier that morning to make a reservation for that afternoon. They offer multiple experiences but we chose the guided cathedral tour. I chose the 6 wine tasting (€30) and Craig chose the 3 (€20) wine tasting. This takes about an hour and a half and includes a super informative guided tour of the incredible cave wine cellar, a tasting of 3 or 6 of their locally produced wines, and a small charcuterie board. We would say this is a MUST DO when in Montepulciano.

Torture Museum for some dark medieval history

Once we were done drinking the delicious Montepulciano wine, we hopped over to the Torture Museum. We didn’t spend much time here and didn’t think it was worth the €10/person price tag. It was, however, interesting nonetheless.

The best Val D’Orcia views

This ended our time in Montepulciano. However, on our way to San Gimignano, we drove past some of the most iconic Tuscany views which were about 30 minutes outside of Montepulciano.

We definitely recommend adding Montepulciano to your Tuscany itinerary. The wine, history, cheese, and views can’t be beat.

Check out our YouTube video of Montepulciano ↓

If you’d like to see more of Montepulciano, we made a YouTube video of our time there (all of the Tuscan hill photo spots are linked in the YouTube video description)

If you got this far, thanks for reading and remember to STAY CLASSLESS 😉