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About learning to speak Italian when you already speak a little bit of Spanish: I did post-doc work at a NATO Advanced Studies Institute class in San Miniato, Italy in the mid-80's. I had taken two years of Spanish in High School, then lived in California where I took adult ed classes in Spanish, then traveled around Mexico and South America where I picked up more Spanish. I was never fluent, but I could communicate with Spanish speakers if they had any desire to understand and communicate with me. Sometimes I had to ask a lot of questions about what some word or phrase meant.

So with that background in Spanish, I prepared for Italian. Before going to Italy, I spent about 2 or 3 months listening to language tapes to learn Italian. I had about a 20 minute walk between my house and campus each day and used that time (coming and going) to learn Italian. At first, knowing Spanish can actually be a problem when trying to learn Italian because they are so similar . . . but often not quite similar enough. Eventually, though, the similarities work in your favor. After about a month in Italy I spoke Italian well enough that NessieSpouse was impressed. She didn't know how much of my conversation with locals was me asking them to repeat or explain. She simply observed fairly long dialogues that ended up with me understanding what we were trying to learn. I always felt that if I had been able to stay in Italy for another month or so, I would be proficient enough that speaking and listening to Italian would be natural and comfortable, but I never really achieved that.

When I was younger, I always thought I might choose to live in Spain or Italy or somewhere in South America some day and figured I was in striking distance of actually being comfortable and relatively fluent in the language of the country. But I recognize now that my motivation and focus on studying languages is not nearly as great as it was when I was younger. I still have boxed audio language courses on the bookshelf in front of me right now, but have become too lazy to want to do the work and study.

If you really think you would like to retire and live in Italy soon, it might serve you well to start some kind of language learning soon, while you are motivated. I think you'll find the Spanish to Italian transition to be reasonably painless.
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