If I add travel insurance to a package for November, then free dining is released, do I lose the insurance price I paid? What if I alter travel dates to fall in the "free dining" window?
I think it depends on where or who you get your insurance from.
I get my travel medical and trip cancellation insurance from a local insurance company but its not just for a single trip. Its for any trip during a one year period.
Best advice I can give is call whoever you are getting the insurance from and they can tell you for sure.
With the Disney insurance, just make sure you keep the same reservation number and it will transfer with the change. The CM will cancel your old res and rebook the new one within the same reservation number to modify rather than cancel your reservation. This transfers the deposit too. If the CM says you must cancel the old res and rebook a totally new reservation with a different res number, tell them no thanks and call back, or ask to speak with a supervisor to change your reservation. They do cancel and re-book, but it's actually a "modify" action within your reservation.
With an outside trip insurance company, most will just change your travel dates slightly for no fee, just call them to make sure.
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