ALONE??? Man, you'll die before you ever get near two days
He doesn't need to be alone; just equip nothing on him (his AC should be zero). No weapons, armour, rings/amulets, *nothing*. I even emptied his inventory, just to be on the safe side, though I'm sure that's not necessary now.
As for location: The "open air" is fine, including woods, water, the Shire area, islands (if you're that far), etc. There was some speculation earlier that dungeons didn't count, but I don't see why they shouldn't -- as I recall, I entered Shurugeon with my Monk-in-training, and when I left and returned to Ishad N'ha, the two days were up. That time was spent almost exclusively in Shurugeon, so dungeons must count...
Anyway, the important thing is HE DOESN'T NEED TO BE ALONE, just naked
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