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Family accommodation in June/July

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Hi everyone, first time here so please excuse any etiquette breaches! We are starting to plan our trip for June/July next year - first time we have been with children aged 8 and 5. My husband speaks reasonable Italian having originally hailed from Trieste but doesn't know Italy apart from Genoa that well, we have spent time in Rome and Venice. My questions are: what would be a good location to stay for a week before we meet up with another family? Thechildren love swimming, so was thinking maybe a villa with pool? Would like somewhere that is different enough from Australia (ie not a resort), so they can get a flavour of the country, little bit of culture, good food, then relaxing in the afternoon. Happy to hire a car, but would like to be able to walk to a village in the evening to have a drink/gelato. We are flying in to Milan so woould get the train and then pick up car.

Many thanks!

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