Vacation Protection (Insurance)

Hello!

Anyone here familiar with travel insurance. I really wanted one that is annual, so I could pay it out monthly and be covered, but the one I found you pay in advance.

We are going on a cruise and Im not wanting to use the cruise line insurance as its too expensive. I used insuremytrip, but Im really confused as to what to pick. Im not sure what Im needing exactly. I just figured I needed something to cover mostly me in case a medical issue arises and I need to be medi flighted off the ship. But what Im also finding is that the insurance doesn’t cover certain things unless it was purchased shortly after booking and its way beyond that date.

Anyone have experience or are familiar with this?

Thanks!