With cancellation cover, one question matters more than “how much does it cost” or “what does it pay for”: when. Trip cancellation cover can't be bought just any time – the terms typically tie the time window to the booking. If you miss it, it won't help to think of it later: the door has closed.
Because the essence of cancellation cover lies in timing: at the moment of booking, the risk of cancellation is still unknown to everyone – that's what allows the insurer to price the cover. As time passes, the chances grow that someone would buy cover already knowing about a problem – and that's exactly what the time window rules out. So the rule isn't there to annoy you; it's what makes the product viable at all: without it, cancellation cover couldn't exist at an affordable price.
The correct order: 1) book the trip (travel agency, flight ticket, accommodation – paying the deposit or the full price); 2) take out cancellation cover immediately, for the amounts already paid and still owed; 3) before departure, arrange the full travel insurance (if you haven't already bought it as one package). “I'll buy it together with the travel insurance before departure” is the most common mistake: you can still buy travel insurance at that point – but the cancellation-cover window will typically have closed by then. More on how cancellation cover works: cancellation cover in depth.
Cancellation cover is for non-refundable costs: the trip price, flight tickets, prepaid accommodation, booking fees – the portion that isn't refunded under the provider's cancellation terms. So the sum insured should match the full, paid value of the trip: under-insured cancellation cover falls short exactly when the trouble is biggest. For a trip paid in instalments (deposit plus balance), follow the policy terms as they apply – typically the full trip price is the benchmark, not just the deposit.
For bookings made close to departure, buying cancellation cover and booking the trip happen almost in the same moment – the time-window question doesn't even arise, but the content of the cover still needs the same scrutiny. Cancellation cover alongside an annual policy is a separate question: see the dedicated article. And most importantly: before buying cancellation cover, read what it pays for and what it doesn't – the value of any cover lives in its terms.
Exactly how many days do I have after booking to buy cancellation cover?
It varies by insurer – typically a short window, measured in days from the booking, applies, with separate rules for last-minute trips. The safe answer: arrange cancellation cover in the same step as the booking, and the question never even comes up.
Should I insure the deposit or the full price?
The full, non-refundable trip price – cancellation-fee bands can rise all the way up to the full price, and under-insured cover falls short exactly when the loss is biggest. When you pay the balance, update the sum insured if the value has grown by then.
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