Your configuration looks almost perfect, and the “Tag pages” looks like a good solution.
There was one thing though. The “Adelaine Cup” page was not relevant to the “Holydays australia” page directly by content keywords, and the fill options was turned off, so I have turned it on: https://i.imgur.com/7xcq4fi.png
Now it should display items from the same tag, even if there are no matches.
If you like my products, don't forget to rate them on codecanyon :)