We normally don't buy
trip insurance, but for this one, we did (NOT thru Disney BTW!! Went thru insuremytrip.com and bought my own policy where I could clearly see the details, not thru some vague "Oh, sure, it probably covers that..." CM schpiel, and it was $20 less than what Disney wanted me to pay.) for several different reasons. If one of our flights is delayed 5 hrs, we're covered for food, hotels, rentals. If an airport is shut down for 24 hrs, we are covered for the whole trip. If our bags get lost, we're covered $100/day/person. If we do have to cancel for some other reason (within their policy, of course), the whole trip is covered. And we both just feel a lot more secure about going during hurricane season with that extra assurance.
Even if you're not flying, there may be some other reason you can't get to your vacation. Or what if you're there and for whatever reason you can't get home (fluke car accident or something)?
Our policy was $94 for the four of us... way better than $160 and still better than the $119 Disney wanted me to pay. We insured the trip for $4K, even tho it's not costing us that much (re-planning the trip for some other time of the year would tho!). That was actually a tip I got from the Unofficial Guide.... Price the policy for how much you're spending, and then raise the amount of the policy to the highest amount you can before the premium changes. The premium for the policy was exactly the same for $3000 as it was for $4000.
Hope that helps!