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If you book your hotel with cancellation options, the plane ticket cancellation fees are up to $250 now - assuming you can use the remainder within a year, but there are free changes during hurricanes. Extra nights, delayed or lost luggage, etc., most risks are rare and/or you can get relief from your homeowners, etc. It's all a matter of opinion and risk assumption, I know - just don't whine when you lose.I'd buy trip insurance during hurricane season, but I don't most of the time for Cozumel trips. The cost of the trip isn't high enough. But when I went to Galapagos- trip insurance for sure.
I take it mainly for the medical coverage as mine doesn't cover international needs, and the rest is gravy. In my younger years, I traveled all over the Caribbean with no coverage at all, had few problems, and never had to beg for help. Pick & chose...
Again, the risk is really small. There's a hundred bucks a year for something I'll probably never use - but I take it. It is nice that most dive insurance plans will provide emergency medical evacuation even for non-diving problems.(Now dive insurance- you'd be a fool not to have it. But for most people the expected value of the pay-out is less than the cost of carrying it. Insurance wouldn't be offered if that wasn't true.)