Ninety days out
Passport validity (six months beyond return, the near-universal rule), visa requirements checked against your actual nationality rather than your neighbour's forum post, and the workshop's deposit conditions read properly. Book flights with a day's margin at the arrival end: itineraries begin on time, and jet lag is a photography problem.
This is also the window for the slow paperwork: drone registrations, restricted-area permits, and any certification a workshop requires (dive cards, competency certificates) with time to fix surprises.
Thirty days out
Insurance — travel and gear both, with the workshop's required covers verified (helicopter evacuation for the treks, water-sports riders for the surf and reef weeks). Vaccination and health requirements against current guidance, not memory. Card and cash strategy for the destination's actual economy.
Read the joining notes end to end, once, aloud if necessary. Every workshop's notes contain one item that surprises somebody, and the somebody who reads at the airport becomes the group's first-morning delay.
One week out
The gear audit: sensors cleaned, firmware current, every battery cycled, cards formatted in the camera they'll serve. The paperwork wallet built: passport, insurance documents, permits, booking confirmations, and paper copies of the lot — the cloud is magnificent until the desert.
Weather checked not for reassurance but for packing corrections, and the dawn pile rehearsed once at home, timed.
The day before
Charge everything chargeable. Confirm the meeting point against the joining notes rather than assumption — 'the airport' has multiple terminals everywhere interesting. Sleep at the destination's schedule if the flight allows.
And the item every checklist forgets: tell your bank the itinerary. The card frozen for suspicious activity in Windhoek is a genre of workshop story we are trying to retire.
What cannot be checklisted
Flexibility is the last item and the least optional. Weather rewrites itineraries, ferries sail early, festivals move with the moon, and the workshop that adapts is the one that was planned well. The paperwork above exists precisely to make the improvisation affordable.
Pack the list, then hold it loosely — the trips that go exactly to plan are the ones nobody tells stories about.