I don’t have an actual checklist but do have a getting to and from the airport plan. About a week before I travel, I made sure I have all the details I need - if it’s an Airbnb and they haven’t contacted me, I get in touch and work out check-in details etc.
I always have travel insurance - and I’ve used it enough to continue using it. But I don’t get it for every trip, just every 6 months or so since I’m constantly on the go.
Before travelling, I do a check that I have all my stuff. Using the same bag and putting stuff in the same spot every time makes that easy.
Checking out SIM card requirements is worth doing since in some places it’s much easier to pick up one at the airport than anywhere else.
I’ll normally book my accommodation for my full time in a place and like to plan things out (eg. buying flights, booking accomm) a fair way in advance. I’m not that comfortable with leaving things to chance/my whims.
I never worry about co-working etc. If I arrive somewhere and find that I don’t have the requirements I need for working, I’ll think about it then but would rather work in my apartment.
Normally when I book a place, I’ll look up the address on google maps and save it so it’s easy to find. I’ll also look up cafes and other places of interest in the neighbourhood and save them.
Workwise, I have everything scheduled ahead in a spreadsheet and add in where I’ll be to that as I make plans so I can adjust for it. If I’m going to only be somewhere short-term then I try to make it a lighter work week, that kind of thing.