Capri

I hope someone can provide first-hand info. In the absence of that, I say "tread cautiously". I went to Ponza (much less busy island, but also a tourist spot) in late September many years ago. It was very, very dead. We did ultimately find a place to stay (hadn't pre-booked), and at least 2 restaurants were open. But a lot of the tourist infrastructure had closed up shop. Ran into a similar situation a bit later during the same trip on the Gargano Peninsula.

Checking ferry/hydrofoil schedules may provide a clue.

Ferries/hydrofoils travel to Capri all year around from Sorrento except in the very worst of weather: the people who live there need to be connected to the services on the mainland. I do see that many of the restaurants don't open for the season until around March 24th - early April so that might be an indication:

http://www.capri.com/en/restaurants

I should note that we were there in mid October and everything was open but we were told that they were getting close to end of the season (Nov. 1).

So did you go in the end? How was it?