We tend to insure expensive cruises and safaris lately, mainly because Brad has had a few bad cases of impacted kidney stones. Up to about 6 years ago I pretty much never bought it at all. And I would say its also location dependent - the more remote the destination, the more likely I am to buy it.

I never include the air since you can get a credit for most of that or redeposit your miles. I also don't insure the value of any independent land trip we might do before and after since I figure I can cancel the hotels without much penalty.

We've never canceled, or had any claims (so far), but as we get older I think its a good idea to just go ahead and buy it.

One interesting thing I just noticed - I just bought one of our nieces a Delta frequent flyer ticket to join us on a ski trip this winter. I transferred points from Amex since we're AA flyers. The terms on the ticket are that you can't redeposit the miles if you cancel within 72 hours of departure. That's a new one for me.