I Pitied The Fool

Arathi Basin - Drop inside the black smith in the middle of the battleground. (or around it, I find inside easier to get done if you just wanna do it and leave)
Culling of Stratholme - Take the portal from Dalaran (violet citadel, upper floor to the left). CoS is located directly south of the entrance to the lair. (south east of the lair) Just go in and drop it inside the entrance and then you can leave.
Winter Grasp - Easiest to do this is when the portal there is up in the portal room in dalaran. If you go there by mount, remember that it's a no-fly zone
Gurubashi Arena - This is in Stranglethorn Vale You can't get this outside the arena itself even though the minimap shows you as in the arena. Make sure the minimap sais "Battle Ring"
Naxxramas - You need to be in a raid group (can consist of only two people) and enter. For those that hasn't you need to go up under the flying building and into it.

Hope this helps someone.

TomWolf @ Sporeggar.EU

obvious night elf mohawk reference

It would seem the toy [item=144339] does not work for this achivement.