The flight in 1920 from Christchurch to Trentham in Wellington was carrying the first air mail between the South and North Islands.
A Fox Moth, with a RNZAF NH90 flying chaperone, will depart Christchurch Airport today, flying past the Air Force Museum of New Zealand at Wigram.
It will then fly over Kaikoura, Omaka, and then across the Cook Strait and land at Trentham Racecourse in Upper Hutt this afternoon.