We used to never take travel insurance, but we do it every time now. Depending on how often you travel, normally you can just get a policy that covers just the time you are out of the country, not a yearly policy. Some travel insurance is pretty darn cheap, if you book it with your air AT THE SAME TIME you book it. However, look at what it covers and what it doesn't! Many of the policies cover medical evac, but at something like $25,000, which isn't enough. As others have pointed out, most insurance does NOT have primary coverage outside the US, so it might well be out of network coverage, which means your co-pays and deductibles could be huge. But again, as someone else said, the elephant in the room is medical evac, which can easily cost $50,000, which if you don't have coverage for that, you'd have to come UP with $50,000 yourself, and HOPE that insurance will reimburse you, at least partially. We have two TTOL sponsors that offer travel insurance. Sky Med covers ONLY medical evac and you can get a yearly policy with them. With Sky Med, they take you HOME, to the closest appropriate hospital to where you live. This means if you live in LA, they will take you to a hospital in LA. However, with some or most of the other policies, they might well take you to Miami, and then you might have to pay for evac to get the rest of the way back home-- or perhaps your health insurance will cover it, but there will definitely be a delay getting you back home. For us, we live in Florida, so this is not a concern. Insure my Trip is a service for you to compare insurance policies side by side, based on the things that you need to insure against. For example, if you're using frequent flyer tickets and staying at your timeshare, if something happens to your trip, your out of pocket loss for those items is minimal. But you may well want to insure for medical expenses and definitely for medical evac. Insure my Trip is great tool for getting exactly the coverages you need. For both Insure my Trip and SkyMed, if you use the links here on TTOL on the sponsors page, we get a small commission and your cost is the same. If you go directly to their websites, we don't get anything out of it.