Thanks for the comments everyone.
As for the suggestions that I hire an escort, I am not looking for sex (in and of itself). What I want is a weekend long social experience with a woman. I want to be able to go places and do things that NTs do BUT on my own terms, and with a date at my side. Unfortunately that is something that I can not do at my current level of social development. I guess it is not practical to pay/bribe a woman to spend time with me.
Just to be explicit about this, I have reached the conclusion that Miami is a bad idea, and I have decided not to go through with it.
I truly believe that what I need is a dating surrogate (as opposed to a sex surrogate). I really want to know why this does not exist! I would gladly be willing to pay a woman that I find attractive $100-200 to date me purely for the social experience. Furthermore, if she had a degree in psychology, she could function as a 'field' social tutor. I would find such a service invaluable! I would imagine that if I could meet a female psychology grad student, she would be perfectly capable of helping me, and would appreciate the extra money she could make for 'pseudo-dating' me.
I think that this deserves it's own thread!