Subject: Italy in August
August is the holiday month for all Italians (excluding me) and you'll find many of them and other foreign tourists in the most famous cities like Venice and Verona, or on the Garda lake but Milano will probably half empty

Anyway at the end of the month everything is slowly coming back to standards. If you take short hops by train, like Milan to Bergamo or Verona to Venice you shouldn't find too much crowd. You can always reserve your seat at any station, if you feel so. If you're travelling by train you'll be forced to lodge in-town, but lodging could be a problem on Garda Lake, the Dolomites, Verona and Venice, because of the time of year and because your budget is about the same of all middle class tourists. Vicenza and Treviso are good choices, but you better check in advance for rooms, maybe on the web or some hotel chains like Best Western or Holiday Inn. If you don't mind, there are usually cheap little pensions everywhere close to railway stations, but you must give a good look at them before. No real B&B in Northern Italy towns that I know of, but you can find some in the Dolomites or on the lake. I don't know about convents.