We always have trip insurance for our Florida vacations.
In the winter, we have winter weather which may delay or cancel our scheduled plans from our airport of departure.
In the summer, we have hurricanes in Florida which may cause us issues either coming or going (and almost did in August 2012 when Hurricane Isaac reared his ugly head).
In the grand scheme of the overall cost of our travels, the insurance cost is minimal and is a peace of mind we find very valuable. God forbid something awful occurs (like a death in the family), then that catastrophe is not compounded by the loss of thousands of dollars for our getaway.
As non-US residents, we also purchase travel medical coverage for when we are in the States. Again, we have never had to use it (touch wood) but knowing its there if we need it is a wonderful comfort....and it has the potential to save us thousands if something actually does go wrong. Well worth the $$ for us.
Thanks to a card upgrade from Visa, our
travel insurance is now provided under our credit card (as long as all components were purchased using that particular method). It might be worth checking your credit card details to see if this might apply to you as well.