In February 1999, Max Grant and David Herrington completed the first kayak circumnavigation of Chatham and Pitt islands. The trip was completed in eight days, five to circumnavigate Chatham Island and three to kayak across Pitt Strait and around Pitt Island and its adjacent islands.

The first Stewart Island solo was achieved by Darryl Anderson from 24 June to 19 July 1999.