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Venice, Tuscany & Positano

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Thanks for taking time out to read my questions, and thanks in advance for any replies, greatly appreciated...totally need help as I am drained from so much research!
So, below are my questions:

1) Picking up rental car, preferably Hertz from Venice (we're staying in Cannaregio), Sunday 31st August...which location is closest? Will be driving to Chianti. Want to avoid Florence.

2) Need to drop car off in Tuscany, guessing Florence, as we need to make our way to Positano. There are various car rental offices, which one is closest to train station?
Do you suggest train from Santa Maria Novella station to Salerno and then ferry to Positano?

Should we hire GPS with rental car or just print maps?

Hope this makes sense, hours researching and brain is fried!
Thanks

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