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Lodging in Italy - Where do you suggest for Rome, Florence, Venice plus?

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We are going to Italy for almost 3 weeks in May! We would love you advice and experience on where to stay in Rome, Florence, Venice, the Lake District (Lake Como) and the Cinque Terra (spelling?) We will be three days in most places. The first 10 days our 18 year old son will be with us, so we will be three people, which limits choices for lodging. Cost matters of course, but so does location, comfort and ambiance. The last week we will be a couple and might want something more romantic than family oriented. Most of all we would like it to be truly Italian. We are leaning towards covent and monasteries, and VRBO (vacation rent by owner) and small Band B's but will consider hotels too. What do you suggest travelers who have been there?

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