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Staying in Tuscany-fly home (Montreal) out of Florence or Rome?

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First off, I am ever so grateful for all the advice in these forums. Have helped so much with trip planning for our first trip to Italy in June 2017 (I like to plan ahead). I do have a couple last questions...

Travelling from Positano to Tuscany (Bucine) - better to rent vehicle in Salerno and drive or train somewhere North and pick up rental car there?

Travelling home from Tuscany to Montreal - easier to fly out of Florence or Rome and where would be best place to drop off rental car?

Thanks!

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