I barely explore health insurance options here Health Insurance
I recommend that you avoid Trip Insurance here
I have a look at Car Insurance here
For me purchase insurance, extended warranties, service plans, and pretty much every other add on option have been utterly useless expenditures. I strongly encourage you to decline these tempting, relatively expensive, features. My credit cards include free short term purchase insurance on objects, and I have never used these benefits.
Importantly, realize that the stuff that you have now is so much less expensive than all the stuff that you used to own. Is it really worth buying a $15 warranty on your $200 backpack, then filing a claim in the incredibly unlikely case that a zipper breaks. Consider the value of your time.
I am positive that the actuaries have done their diligence, and insurance is a massive profit center. So instead my philosophy is to ‘self insure’, at a much more modest long term cost, as noted in Durables.
Everything eventually fails and breaks, and mostly for fairly obvious reasons (such as ‘dropped from a great height into a sewage ditch by a feckless piker’), which are not covered by most add on insurance.
Look after your spendy stuff, and get new shiny things when they blow up or wander off.