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Okay so, winter is coming and we are considering which hike we should do...

Ciretia are as follows roughly:
3 days
A pass of some sort to get above 3000m
No alpine climbing (Although some may be considered)
Decent level of fitness required
A peak would be a bonus
Something that you will remeber all of summer

If there is heavy snow fall can a "path" be followed, or d you have GPS data?

Consider the Giant's Castle area - several good 3 day options there. I tend to save this area for winter because most of the shepherds move away. You can work out various combinations of passes from Judge Pass all the way through to Giants Pass, with some worthy 3000m peaks along the way. Then there is the Giant's Castle massif. The summit itself is a very worthwhile destination - most 3300m+ peaks are away from the edge...not this one! You can use Giants Pass up and down, or combine it with Elandshoek Pass coming down the South Ridge, or do Eastern Gully if you feeling really adventurous (does get filled with snow, requiring gear). You can also check out some of the classic ice routes while there. Mind the violent winds that seem to hammer the massif though. GPS data for many of these passes are in the Downloads section.

I suggest Lotheni.It has a far more 'remote' feeling than Giants.
Day1: Up Butress Pass. A doddle really!But gets you to the summit quickly.
Day2:Walk north bagging Redi Peak, 3rd highest.Continue 'north' camping near summit of eNtubeni Pass.
Day3: Down eNtubeni Pass back to Lotheni Main camp.Awesome waterfall en route.
Happy hiking!