I like the idea of having protection in place before the actual trip starts, especially when flights and hotels are booked months ahead, and https://www.globelink.co.uk/policy-options/annual-travel-insurance.html (https://www.globelink.co.uk/policy-options/annual-travel-insurance.html) is relevant for checking cancellation cover. Do you prefer starting an annual policy immediately or closer to the first departure date?