We are renting a car in Milan to travel to Castelrotto, spend 2 nights and then head to Venice. We can either drop the car off in Verona and catch the train for the next part of our trip, or keep it and drop it off in Venice(our next stop). Any thoughts?
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Just drop it off in Venice. I would suggest the airport. It is easy to get to an the end of the A27. then take the bus in to Venice. Airport dropff should not add any extra charge to the rental. If you have the time, there are some interesting spots to stop along the way. Asolo, Cittadella, Bassano del Grappa and Castelfranco Veneto for smaller towns.
Dropping in Venice is easy. You can drive across the lagoon bridge and to the Piazzale Roma where the rental agencies are located. That would save you one less transfer and you can get onto a vaporetto at Piazzale Roma and go to your hotel.
From our past experience in Verona and Venice I would have to agree with previous posters--easy to drop off in Venice. We have dropped cars at the airport and also at Piazella Roma and did it with no problems.