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Paying My Way Through Italy

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While traveling through Italy from 9/20-10/11, I would prefer to pay for most everything in cash, including my hotel stays and rental cars, etc.

My question is if it is acceptable/customary to receive a better deal if you are using cash while traveling? In the US, of course, you can often can a better rate from smaller business owners when using cash.

However, perhaps it is not the best strategy to go through Italy with that much cash on me. Maybe the experienced travelers can discuss their strategies for paying their way through Italy?

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