For people that live close enough to the U.S. border or frequently jaunt across to save on U.S. only deals, getting travel insurance should be a high priority. When you factor in the total amount of time you spend across the border, even if it's only for a few hours at a time, the chance of something going wrong increases significantly. Unfortunately, purchasing traditional travel insurance every time you skip across isn't convenient or the most economical. That's why multi-trip insurance (sometime known as annual insurance) was created. It's usually a yearly plan that covers frequent small trips out of the country. It's also one of the best deals for the frequent border crosser.