After a few days in Siena, we headed to Colle di Val d’Elsa, where we were hosted by Cecchi Winery, one of the leading producers in Chianti. It took me a while to figure out that there were two distinct parts of the town, the newer, lower part and the “colle alta” or the “high hill.”

Our hotel for the night was in that fascinating latter part of town, which dates back to the 11th Century as a medieval fortress (and the lower part of town is, well, rather uninspiring, to say the least).

We were scheduled to have dinner with Andrea Cecchi later that night, so that gave us a bit of time to explore the town, which has long been known as a center for glass blowing. As we strolled through the narrow streets, there were two thoughts that would repeatedly race through my mind: 1. The town was beautiful; and 2. We were seemingly the only ones there.

The imposing walled entrance to the upper part of the town.

We arrived just in time for lunch at a restaurant on the ramparts.

My wife hates posing for pictures, but she is far more photogenic than am I.

After exploring the town all day, we headed to the Foresteria Villa Cerna, a restaurant opened by the Cecchi family right across the street from the winery. There we met Andrea Cecchi, CEO of the winery, his lovely daughter, and Giacomo Tarquini, the media manager at Cecchi.

The chef (right) and the wine director came out to explain each of the traditional courses.

There was also plenty of wine, of course.

Andrea delved a bit into the history of the company,  founded by his great-grandfather, Luigi, in 1893. It was his grandfather, also Luigi Cecchi, however, who had the vision to buy multiple properties (including the now iconic Villa Cerna) in the 1960s, but he anticipated the formal appellation of Chianti in 1966 and got in while the land was still relatively inexpensive. Many of those vineyards he initially planted are the source of some of the winery’s finest wines today.

Andrea’s father (another Luigi) continued to acquire property, but ventured a bit further out, buying a property in Maremma (Western Tuscany) in 1996 and a vineyard in Umbria in 2000.

Andrea and his brother, Cesare (the company’s president) have followed suit, adding the historical estate Villa Rosa in 2015.

The conversation was far more than “shop talk” as we discussed family, politics, travel, and even cycling. The three hours passed far too quickly though, and we headed back to our hilltop retreat.

We would see Andrea again the following day as we headed back to the winery, for a tour and a more formal tasting of the wines, but it would be hard to improve the impression we already had.