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Hotel availability from Rome to Sicily without reservations in mid May?

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Will be driving from Rome to Sicily and spending a week traveling throughout Sicily for a week in mid May. I usually just "wing it" and feel confident I can find a place to stay each evening with little problem. This provides the greatest freedom for spontaneous travel. However, my traveling companion is less convinced and feels reservations are a must so we don't end up sleeping in the car. Therefore, I pose this question for help in settling the issue. Places we intend to visit include Sorrento on the Amalfi coast and Trapani and Taormina in Sicily. Also considering going to the island of Lipari or perhaps to Malta. Any input is appreciated.

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