To get the most protection, you should buy travel cancellation insurance as soon as you make your first non-refundable deposit (e.g., booking your flights or hotel). In 2026, many insurance benefits are time-sensitive. For example, the "Cancel For Any Reason" (CFAR) upgrade usually must be purchased within 10 to 21 days of your initial trip payment. Furthermore, insurance only covers "unforeseeable" events; if you wait until a hurricane is named or you start feeling ill, it is too late to buy coverage for those specific issues. By purchasing early, you activate "pre-departure" protection, meaning if a family member falls sick a month before your trip and you have to cancel, you are covered. Most 2026 policies also include coverage for "Pre-existing Medical Conditions" only if the plan is purchased shortly after your first trip payment. Waiting until the day before your flight leaves you vulnerable to any mishaps that occur during the weeks or months leading up to your departure.