For me, "travel insurance" entails three parts, of which your question is directed at the first, reimbursement for the cost of travel if the trip is interrupted or canceled, for various reasons including personal illness, missed flights, or bad weather. I try to plan my flights for enough time to connect, but you could in theory consider the small risk of missing a trip due to a mechanical, a broken leg or a hurricane. The latter would be a reason, in my mind, for some coverage being worthwhile if you are traveling during storm season in the Caribbean. Interestingly, there are websites that can allow you to look up how often a hurricane has passed within a selected destination within a particular time period, if you wanted to see what your historic risk might be. I bought such insurance for a vacation last year, and didn't need it, but a TS passed us on my last day and ended up forming Hurricane Irene. Generally however, I self insure. You should however consider two other parts of dive travel insurance: dive medical and dive gear. Dive medical has been described in detail elsewhere, and you may not need any more input, but consider whether your insurance is primary or secondary, and how would it pay if you needed a chamber ride in a foreign country. My own insurance will pay if I need a chamber ride, they say. I just have to submit a receipt and a copy of my medical record! Of course, I'd be on the hook for what could be many thousands if I got bent, and would have to find a way of covering it in the field. Lastly, dive gear (by which I mostly refer to cameras and other electronics) may very well not be covered by your personal property insurance. In my research, I have found that some "dive accident" insurance only covers gear damaged in a medical dive emergency, not from being dropped to the deck or flooded. Even dedicated dive gear insurance usually doesn't cover gear "lost" eg dropped overboard or abandoned on a dive, there has to be a piece left to prove it was damaged. So, insurance is complicated. Personally, I mostly self insure for travel costs, I buy additional medical coverage to cover high end costs like hospitalization and evacuation, and I buy dedicated gear equipment because I have a video setup that would be too difficult for me to replace if I flood it out.