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The question of whether or not to purchase travel insurance isn't easily answered. Some people throw caution to the winds and never get any insurance at all, much less travel insurance. Of course, these same folks may end up in debt for life if they're ever in a disabling accident. Travel insurance poses some new questions -- some vacations are low risk and cost very little money and therefore probably aren't worth insuring. A vacation that includes hang gliding on a remote island during hurricane season, on the other hand, may be worth insuring. If you're prone to injury, illness or flat-out bad luck, you might want to consider insuring your trip as well.