PoliciesCame to the USA several years ago from the UK, and in the UK (in my experience at least) it's normal to buy travel insurance when you book your holiday. It's generally not very expensive (£50 per trip? or maybe £200 for the year, IIRC). After researching the US insurance market, I see it's not nearly as cheap. Very weird. UK companies need to come over here and start competing! I want it mainly because if my gear is lost (skis, boots, accessories, whatever), I don't want to have to replace it all when I get home AND have to pay for rentals while I'm on holiday. That's the rationale.
Travel America (?) has an annual policy, but it's still not very good for replacement cost of skis. My private healthcare insurance covers all of that, but homeowner's insurance will only cover skis if there is evidence of a break-in. That is, if someone takes the skis on the hill, it's not covered, but if they break into my hotel room or car and steal them, I am covered. Loss by airline is not covered by home insurance. Perhaps it's just more peace of mind and past experience than logic which makes me want to get insurance. I'm used to having that back up so that I know my vacation isn't ruined by unexpected events. I don't expect coverage for extreme sports activity since I don't do anything "extreme." Maybe I'll look into that if I ever do, but not anticipating it in this lifetime.
I'm going to continue researching for the right annual policy, and if I find it I'll post details. Not that it has happened to me yet (though AA misplaced for a day my bag on the way back from my last trip), but I like to know I can refer to someone to sort out the problems if they happen at the beginning of my trip. It's part of the relaxing vacation experience, and I'll pay for it. I don't want to be stressing all throughout my holiday.