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Venice or not

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My husband and I will be traveling to Italy in May with another couple. We are flying into Rome and spending 3 nights. Our plan is to rent a car and head to Positano for 3 nights. We will stop in Pompeii on our way south. Will it be safe to leave our luggage in the car especially if we end up with a vehicle with no trunk for the time we tour Pompeii?

After Positano we are staying outside of Cortona for 2 nights. All of those hotels are already booked. Now the question is how to spend the rest of our time. We have 5 nights left (the 6th night is staying at the Milan airport). We were thinking of staying in the Siena area for one night, one night in Florence and turning in the car, then a train to Venice for 24 hours, then on to Cinque Terre for 2 nights before heading to Milan airport. Is it worth going to the expense and time to go to Venice for 24 hours? Should we add another day to Tuscany countryside or Florence instead?

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