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For example, if you’ve pre-booked over five holidays and plan to make up for a lot of lost time, I’d go ahead with an annual policy (as it should work out cheaper) than several single trip policies. The majority of providers now offer pro-rata refunds for the unused portion of the year.
Alternatively, if you have one or two trips planned this upcoming year, I’d stick with a single trip policy - which you can usually move to another date if you’ve had to reschedule your trip (as long as the trip is still taken within 12 months).