It was like being-tag teamed by two used car salesmen. Recently I was driving around a visiting friend who was dying to try some amazing Brunello from the area and wanted to go visit Montalcino. I decided to take him to the Enoteca la Fortezza in Montalcino where he’d have a chance to taste numerous high-end Brunellos at the same time.

Held under the regal arches of the Teatro of Cortona, the Strada dei Vini Cortona, end of summer wine event was a small but very welcoming and a nice representation of some of the great local Cortona wines. With two sommeliers actively pouring wines and available to answer any general wine questions, it was a nice way to taste a decently sized pour of the available 25 or so wines. As opposed to the U.S. where you often meet winemakers or a...