Well, Jay, you'll find my answer surprising. And i don't think it's that helpful to current newsboard readers, because it's so old an observation. Italy is less, well ... well-off than it was in the 1980s. The fact that Sorrento has some old buildings does not make it a San Gimigniano, does it?
On business, I went to Reggio Nell' Emilia about four times in the late 1980's. Most of that small city is post-war new construction, although I don't remember much reinforced concrete. What struck me was that I never heard anyone on the street or in a restaurant speaking English. The passeggiata each night, on the full-sized sidewalks of a very urban street was full of slow-strolling, smiling families. There was no struggle to "get somewhere", or to complete the Rick Steves-inspired five major sites each 24 hours. I knew the town well enough to wander around to a different restaurant each night, or to the train station on my day off. I stayed in a family-owned hotel, the Scudo d'Italia, with no air-conditioning (I had a fan) but a lunch-only restaurant.
I had no illusion of being in a wooden village with the soldiers of "Band of Brothers". But I did have the feeling of being in a prosperous, happy place. I later read in the New York Times that, besides an educational system of interest to American scholars, the city was known as a center of international art theft rings! On a later visit, I brought a sleeve of "We are Happy to Serve You" "Greek" paper coffee cups. When I presented one at a coffee bar on the way to work, asking "da portare via", they looked at me like I had just landed from the planet Mars. Why would I want to skip the china cups and the good fellowship of the stand-up breakfast from a heated pastry display case?
Before the Great Recession, I had a similar feeling in Turnhout, Belgium. Of course, the food is not as good there.
Jay, I had little such feeling in Tuscany or adjacent provinces. The crush of tourism was just too strong. Although the town of Castiglione del Lago is much less physically charming than the more popular places in the area, it's hard to recommend. But the absence of crowds on the summer day we were there lent it a feeling of being a place where real people live, not just those in the tourist industry.
Returning to the topic, my wife and I cheerfully chose Sorrento for a five-night stay in 2014, mainly for it's transportation opportunities. I spent a lot of money for a cliffside terrace with an incredible view, and a swimming platform reached by the hotel elevator. We were entirely satisfied with our choices. That doesn't mean that we cherish our stay there in the way that repeat sun-seekers from pasty-faced England seem to. Maybe I've been to too many islands in the Caribbean.
