I can't tell you anything specific about Lecce, but I certainly wouldn't sweat the language problem unless you're planning on giving long speeches on arcane subjects - like replica watches, for instance!
Everybody more or less has a few words of English these days, and life is not complicated to the point that you won't be able to make your needs, ideas, etc., known.
In the meantime, why not read up a bit on where you're going via Frommer's, TripAdvisor, Lonely Planet and the tons of other stuff on the Net?