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Split CMS collection list into dates


I have a client who needs a detailed CMS structure and I cannot find, (yet) a solution.
What he wants is:
A collection page that lists sites he’s visited. Each site to have a dropdown menu of the dates he’s visited. Then each of these dates to be linked to a gallery of images for that specific date that opens on a seperate page.

Do we need to set up a collection for each date or can we tag the images with dates so they are grouped by date and not collection?

Thanks in advance

Here is my public share link:
(how to access public share link)