Hi,

The answer to this is probably obvious so I apologize, but I am not sure how to proceed.
I am about to transfer my domain to another registrar, what happens with my vanity nameservers? how do I transfer them from the old registrar to the new registrar? or do they get automatically transferred together with the domain?

They don't get transferred no, once you transfer a domain from one registrar to another that's all that is transferred is the domain and it's respective WHOIS information, you will need to recreate all your records accordingly at the new registrar.

Thanks for replying.
So if I understand you correctly I just enter the vanity nameservers over at the new registrar, as if I was registering new ones?

I do believe that is correct, yes.