I can’t decide whether to add travel insurance to my WDW package. I have put off this decision as long as possible, since I need to pay my package balance by Thursday. I have never purchased travel insurance, but then I have never traveled to WDW in December for a 14 night trip.
Have you found having travel insurance beneficial?
I only get travel insurance when I travel overseas in case someone needs medical attention or something so my bank account doesn’t get screwed over.
Most other things that I work about that could pop up are usually covered by whatever companies I’ve booked through.
Also check your credit card is you booked with one, many have insurance
My worry is a flight cancellation delaying my arrival. My room, tickets, free dining (with a paid upgrade to include table service) are all on a package that will already be paid for. Flying on Dec. 21, if the flight was cancelled due to weather (or whatever) when could I even get there.
Would you be purchasing the travel insurance through Disney? If yes, another question for you…
Would the flight also be purchased through Disney?
If your worry is the flight cancellation, then I would ensure that whatever travel insurance you are getting will cover the flights. If you are getting insurance through Disney as an add-on for your WDW package AND it works how the Disney Cruise travel insurance works, the flights are only covered if you also purchase the flights through Disney. So I would double check that. And also check into what they will cover for delays/cancellations re: flights. Some insurances only cover interruption on flights for named storms (i.e. tropical storms/hurricanes) some cover only after so many hours of a delay. So look into that.
We don’t ever buy insurance for domestic travel, even air travel in winter months, but we do for cruises where the vacation cannot happen if we miss the all aboard time. And we don’t tend to book anything domestic that isn’t refundable within a 2-7 day timeframe before travel (so we usually also avoid packages with Disney as they usually require 30 days in advance cancellation notice & then charge a travel insurance to be able to change even if emergencies come up).
I would def shop around, Disney are likely to charge Disney prices for insurance too 
You can usually get something really affordable just for your own piece of mind
I don’t usually get travel insurance for WDW, but I always get it for DCL. Medical evacuation from a cruise ship is crazy expensive.
Travel insurance and health insurance are 2 separate things. And yes, evacs are crazy expensive so you want to make sure anything you purchase covers that.
I read that you can just change your dates if it’s after the deadline to cancel. Can you also cancel a few days later once dates are moved?
I guess this doesn’t help if something happens day of or during the trip and it gets cut short.
I agree with lolabear_la. One basically needs to take the time and read ALL the fine print in whatever travel insurance policy you are considering. Then decide if any of the conditions and exclusions covered apply to you, and what the likelihood is of that happening.
I bought a policy (not thru Disney) years ago for a trip to WDW while COVID was going on. Had to cancel for medical reasons, but was denied coverage. When I reread the policy I wondered how I could be that stupid. But that’s just me. So just saying, do the “due diligence” with this particular product ahead of time.
Some travel insurance covers illness and accidents during the trip.
Yes. The cruise insurance I buy covers by travel issues and health issues.