This is what planning a 19-day drive/hike trip in the Otago and Canterbury areas of the South Island looks like

The NZ Department of Conservation (DOC) provides this mapping tool as a way to create a looped itinerary from CHC. As of today (5 days from departure) my trip is maybe 60% firm. I have a car, two nights in a hostel in Akaroa, outside Christchurch. There are plenty of geographical and logistical challenges in the way of getting from Point A to Point B. But that's why I do it. My plan will likely be more kiwis and fewer foreigners, with a fair amount of solo day walking as well. So far it's 2 nights-ish in Mt Somers, Kopuwai conservation area, Glenorchy, Ahuriri conservation area, Mt Cook NP and substantial fudging. Now I'm working on the Queenstown and wanaka area with no tourists and limited backtracking. Ahhh