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Travel Insurance: Hotel Cancellation Fees

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Hello. I can't take anymore chances, for the first time I'm planning on getting Travel Insurance for 3 weeks Italy trip. I'm a US citizen. Please share your knowledge and experiences. Especially your "wish I've known that". For this trip, I made my first payment for flight booking 2 days ago.

Aside from airfare, the big bulk of my travel $$$ will go to hotels. I want to to insure or cover Hotel Cancellation Fees/Penalties - I have NOT prepaid any accommodations. But I have Hotel Cancellation Penalties which could run up to mid 4 digits( $X,000) if I cancel '4-3 to 1 Week(s)' prior to my departure. Most of it is in the Amalfi Coast. You guys know that hotels/villas in the area have longer and higher penalties for cancellation (not 48 hrs prior to arrival).

In travel insurance websites, the "trip cost" is asked when you do "trip quotes". It specifies your total non-refundable payments and deposits. Should I add my "hotel cancellation fees" to that? Take note that I have reserved but not pre-paid any deposit to hotels. Fees will only be charged to credit card upon cancellation within those time frames.

One insurance company rep told me to add those Hotel Cancellation Fees to total trip cost. Another rep told me that since I have not paid any deposit, I cannot add those Hotel Cancellation fees. That made me go go "huh"? Hotel Cancellation Fees are one of the major $$$ outlay if these trip is cancelled for a legitimate reason.

Thanks in advance for your input.

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