Insuremytrip has a wonderful section/tutorial about why you would want to purchase trip insurance. It's worth reading. Trip insurance does not cover recoverable expenses. So, if you want to cover your flight and hotel, then it "might" not be worth the expense, since you can usually rebook a flight, even if it is not cancellable. Plus most hotels have a cancellation window. We never got trip insurance until I turned 65, then it became mandatory since Medicare does not cover non-American areas.