I've made about 45 trips to Negril in the last 25 years & only recently have purchased trip insurance. I think it was about $25 for my upcoming summer trip. Last year it cost a bit more, maybe $36. Even though I'm in my 60's, I'm in great health & have no medical issues. Still... you never know. I buy mine only in case something happens w/ my almost 97 y.o. mom & I have to return home. 2010 was the first time I bought trip insurance. Ironically, she was hospitalized w/ pneumonia that summer but was not in the hospital very long so there was no need to return home. (I stay for 5-7 weeks when in JA.) I hope all goes well this summer too. One of my first trips in the 80's I opted out of a snorkeling trip when friends helped rescue a snorkeler who had been "run over" & severely injured by a boat's propeller. The man was in bad shape & eventually airlifted to Miami, we heard. You'd think that would have inspired me to get insurance every trip through the years but it didn't. Now, it just makes sense.