Until some of his guests/guards decide they want some servant girl's ass and you end up raped. And then you end dead in a gutter since Magister Illyio doesn't approve of rape under his roof and they need to cover their crime.
Anyways for a male the best option would be to start in the West in the Lannisport and head to Oldtown to the Maesters of Citadel. It is really the best one hands down for one simple reason and I can't believe more people here didn't realize it...
You can read and write in the world without printing press... This skill for survival you already know and you don't even need to insinuate your way into Citadel itself by bribing or otherwise to be useful to them. They have lots and lots of books and their adepts need to actually learn stuff instead of spending hours and hours by copying books.
Thats bare minimum you can achieve being able to read and write. 99% of men on this forum could follow this plan and succeed given they manage to make the journey from Lannisport to Oldtown - which is the trickiest part and part where you are the most vulnerable, because ships sink, the captain may turn out to be a dishonourable man and screw you over and if you opt to travel by roads - well they are not exactly safe either.
Why Oldtown you might ask? several reasons:
guaranteed employment, as far south as the south can be, port city - in case the white walkers decide to finally invade you will have plenty of time and savings (in case you got robbed at one point) to bail from the continent
For a woman it is a little bit more trickier. The best option is to follow the same route only to masquarade as a man. Which means apart from preparing a good plan in advance on how to get From Oldtown to Lannisport you also need to prepare in advance and learn how to act and look to pass as a man. You don't want to end up in subservient postion in that chauvinistic world trust me.
Edited by Smitevil, Jun 29, 2012 @ 2:01 AM.