There are at least 2 options that I know of.
Firstly you can make a change in preferences so that the social metadata and book cover get sent along with your book when you transfer to the Kindle.
NB: When I do this and open a book on my Kindle to look at this data I have to press previous page as it seems to open after the data. If I press back a few times I go backwards past the cover and into the data.
Preferences, Common options, Structure, Insert Metadata as page at start of book
The second option is to create a catalog.
A catalog is a file that gets transferred to you Kindle that can contain your entire library if you wish. It is searchable, and can include as much or as little info as you like.
It will have the covers, tags, summaries, social metadata the lot if you want.
There is a sticky for it in the Calibre forum here:-
https://www.mobileread.com/forums/showthread.php?t=71143
Brewjohno.