You can buy annual holiday 1 stop travel insurance either as a single trip policy or an annual one. In most cases if you intend to go away more than once a year, you may find it cheaper to buy an annual travel insurance policy rather than 2 single polices.
As with many different types of insurance there may be an excess payment associated with any claim. This may mean that it would not be worth claiming for a small value. Check to see what if any excess charge there is with your travel insurance policy.
Many low cost airline operators do not compensate for late departure or cancellation, the most they will do is transfer your ticket or refund the ticket price. They recommend your have annual holiday 1 stop travel insurance to protect you financially from these circumstances. Of course many offer their own policies online when you book.