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Extended stay in Italy

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If I was to try an extended stay in Italy how long could I stay on passport from US ? I could work as online college professor anywhere with Internet access. Which seafront town would be least expensive and easy access to visit sites in Italy or surrounding countries? I've visited Sorrento, but wondered what northern cities were like. My husband wants to be near the water, but near train routes or airports so we could travel throughout Europe. Or would it be best to station ourselves in an English speaking country and travel to Italy?

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