We had decided to stay in the center of Montepulciano so we could explore the medieval city as well as take day trips to the surrounding countryside. We dragged our suitcase up winding paths and staircases to reach the Meuble Evoe Hotel, and were greeted by the delightful Angela.

We checked in and then took a stroll up to the Piazza Grande to enjoy the view.

Walking a bit further we found pretty gardens and a building with a glass floor, as there were ancient ruins beneath that the town wanted to preserve.

We stopped at the Boscarelli wine shop for lunch, and then did a tasting with Nicolo. Nicolo’s parents had started the Boscarelli winery, and now it was run by Nicolo and his brother, Luca. The family winery was featured in Wine Spectator magazine. It was interesting to spend the afternoon hanging out, talking wine.

That evening we had drinks on the terrace of a restaurant that hung off a cliff overlooking the valley. Then we moved on to dinner at a wonderful local restaurant where we stayed very late talking to the friendly owner.

Suddenly we heard drums. Had they followed us from Siena? Investigating, we found young people practicing drums and flag twirling in the square for a holiday the next day that would celebrate the different contradas in Montepulciano. Band practice in the town square at midnight? Why not?

In the morning we went exploring. We drove to find the hilltop village, Civita di Bagnoregio. We’d only ever seen it before as a Google screen saver! We took the looong walk through the town and then up the narrow bridge to the village.

It was a delightful day to wander the town and have lunch in a cafe.

Driving back through Umbria we saw other cool sights along the way, like Orvieto village and Castel Viscardo.

It was fun to end each day back in Montepulciano, wander the streets and then watch the sunset from a different plaza each night.

Angela had suggested a day trip to nearby Pienza, so we started our second day with that.

It was an adorable town, and we spent a wonderful morning wandering through.

Then on to beautiful Montalcino for a look around and an afternoon espresso. We’d really gotten into the Italian culture!

A quick change of clothes in the car (we’ve only done that a couple of times) and we moved on to tour Banfi Winery.

We met at the Banfi Castle, and our guide, Paul, had us drive down the hill to meet at the actual winery. Paul was informative and humorous as he told us of Banfi’s winemaking as well as their olive oil and plum production. Then we drove back up to the Banfi Castle for a fun wine tasting.

Montepulciano was a wonderful stop, and we’d do it again any time!