Jen, never, but I would guess that winter in the cities would be about the best time to go…maybe not the small towns in Puglia but Matera, Palermo, Catania, Lecce, Bari, a big yes in my opinion.
I am hoping to go to Bari and south next May. Long ago I mentioned a SlowFood restaurant that we loved in Taviano. They have now changed their name from dialect and now rent rooms, and both rooms and restaurant are now named Casa Martino; I have written three times to ask for a booking in their adjacent hotel but have not received a response. I will phone them when I go this week. Same issue with a hotel in Bari–three e-mails and no reply!
I would LOVE to go to the cities in the winter. Even Matera…I tried to find a hotel In Matera that was in the upper town and not in the sassi but ended up in the sassi last fall (very upscale and glorious Sextantio della Civita) in winter the upper town would be the place to stay, in my not-very-well informed opinion. Most people limit their roaming to the sassi but I love the upper town…the main market is there, the bank, passeggiata, and the local life of that city.
While I am at this topic, if you have not been to Sevilla, winter is THE time to go. I spend every March now, solo, in Andalucia. I go to a small inn outside Vejer which is easy to access from Sevilla, Cadiz, or Jerez. This March I will be 5 nights in Sevilla and most of the rest of the month near Vejer. There are flights from southern Spain to southern Italy. Sevilla might be among the most compelling cities in Europe, to me. I could not think of a better plan than a few nights there and a small flight to wherever you can find in southern Italy. Ryan Air seems to fly every route in Europe and although I have never flown with them… They even fly Catania-Cagliari!!
Did you ever go to Sardinia??? I don’t now how many more trips my partner will be able to manage so the island is on my list as well! What can you expect from someone who majored in geography in college!!!