I cancelled out of my 4-week UK holiday, which was booked for late August through late September. Part of it was with HF Holidays. They offered the choice of a refund or a change from heritage railways of Scotland to self-guided walking based in the same country house hotel. The remaining time was on my own in Edinburgh, Manchester and Holmfirth, all in fully refundable lodgings. The airline, Delta, offered all booked passengers the opportunity to cancel and rebook within a couple of years without the usual change fee.
I used my credit with HF (and more) to book a couple of their holidays in October of this year, the Bloomsbury Group literary tour based at the West Sussex house and a week's self-guided walking at Lulworth Cove. For me, self-guided "walking" is self-guided touring via local buses to the best photo ops in the area on clear days and to local history museums on rainy days. Between those two I have a reservation for a week's lodging at the youth hostel on Euston Road in London (single, all en suite), because it's so late in the season that the LSE autumn term will have begun so my favorite residence hall on Endsleigh Place will be housing students instead of operating as a B&B.
I made the airline reservations on the day that my return flights became available for sale, December 3rd.
The travel cancellation insurance will come later, because no one is insuring against cancellation due to pandemic. I'll buy it as soon as the infection rate has been down to a level indicating a low transmission rate for long enough that it looks reliable, since they won't pay for cancellation due to fear of infection.