After comparing several different options, I have to say that the very popular Annual Travel Insurance policies from Allianz and others are really a poor value for most travelers.
Compare the "basic" plan for two travelers on Allianz with a 24-day term policy through Amex:
Allianz vs Amex:
Cost: $276 vs $64.
Medical: $20k vs $100k
Medical Transport: Same, and both are pretty limited. A specific medical transport policy is much more liberal.
Trip Cancellation: $0 vs $0.
The Allianz annual policy does give you some coverages that I declined when I worked up my Amex quote.
Lost/Damaged bags (you have statutory coverage already in addition to any credit card or other coverages you access)
Travel Delay: $200/d, max of $600. (again, you have this coverage already statutorily)
Rental Car: $45k. Sound great, but you may already have coverage through your credit card And if you're traveling in an excluded country like Italy or Ireland, you still will be required to purchase insurance... read the fine print to see if that required purchase doesn't void this coverage.
I did compare Apples to Apples with a term policy through Allianz. Again it was more expensive for less coverage. Their highest coverage was only $75k medical and cost $234 ($170 more than the same term Amex policy). Even their cheapest term policy was $94 for only $10k of medical coverage.
All I'm saying is to compare the cost of a multiple Term policies vs pushing the easy button on an Annual policy. You get more coverage at a cheaper price. It took less than five minutes to buy the Amex policy so it's not particularly heavy lifting to do it a couple times during your travel year.