@Bearens
First and foremost, perceptions of safety in South Africa depend on who you ask. Safety cannot be compared to that in Europe by any means. Events like the August taxi strike also tend to increase reports of unsafety.
The Cape Cross is a truly beautiful route and one of my favourites. While I haven't done the whole route recently, I do cycle many parts of the Cape Cross routes from the Stellenbosch side often. There are certain roads to be wary of near Stellenbosch, but in most cases, I haven't experienced issues personally. As a South African, I may be more tolerant of certain scenarios in the country than you would be.
Depending on how many days you plan to complete the route, I would avoid cycling in the evenings. Doing a set amount of kilometres per day, town-to-town, and staying over to enjoy local hospitality is a good approach. Many of the roads you'll ride are on private farmland - likely safer than public roads. This is part of the Cape Cycle Route Initiative set up by the Western Cape Government and Wesgro to promote cycling tourism in the region.
You can find more detailed information on the official website:
https://capecycleroutes.co.za/route
Cape Cross route:
https://capecycleroutes.co.za/route/cross-cape-route
Accommodation:
https://capecycleroutes.co.za/accommodation
When riding, be sensible, ensure you have a cell phone and possibly a tracking device like a Spot. While you'd likely have cell reception most of the time, load shedding can sometimes disrupt cell towers. You can rent a Spot here: https://sat4rent.co.za/612-2/
Which end are you starting from, Stellenbosch or Plettenberg Bay? If Stellenbosch, let me know - I can ride the first part with you or show you some local routes when here.
