と and や can be used to list things with the difference being that と indicates an exhaustive list, while や means that there can be more in the list, than what’s mentioned.
I know that と can also mean ‘with’ in cases like
e.g.: “公園になおさんと行きました” = “I went to the park with Nao”.
Coul I replace the と with a や to say that I went there with Nao and some more?
Like this:
“公園になおさんや行きました” = “I went to the park with Nao (and someone else).”?
Reading the grammar dictionary seems to imply that no, you can’t. If you want to imply the presence of others, you can just say ～たち, though. なおさんたちと.
I feel like “公園になおさんと人たちと行きました” would be my first guess, but not sure, if that would work?
I have the impression that ~たち makes things plural, so could なおさんたち sound like there are multiple Naos, like there are many people with the name Nao? I mean, would it sound like I went to the park with several people called Nao, if I said “公園になおさんたちと行きました”?
なおさんたち = Nao-san and the others.
Not even sure how you’d say more than one person named Nao. なおたちさん, maybe?
ーたち is one of the cooler things about Japanese grammar. You’re referring to the group that なおさん is part of, rather than pluralising なおさん like you would in most languages.
I tend to think of や as “things like”, or “such as”, rather than “and”. Maybe that will help you?
Yeah, no one would think なおさんたち meant many people named なお.
I guess in extremely casual usage, you could say なおさんズ to mean several people named “Nao”. That’s the English -s plural ending rendered in katakana. 
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