Here's the scenario:
I am preparing for the South Coast Track and I have found a potential hiking partner who I don't know very well and I am not sure if he is up to the challenge. If he's not up to it I want to find out beforehand so, in order to get a better idea, I would like to load up our bags and go on the toughest day hike you can muster (let's say 15-25 km) and within an hour's drive from Hobart.
Mt. Wellington or Collins cap have been suggested to me, but as I have not seen these trails I want to make sure they are indeed tough. While spectacular scenery would be a plus, this is primarily a training exercise so difficulty is the top priority. I want the kind of hike that could drive a non-whinger to whinge. I would prefer a trail that is relatively well marked so I won't need a map. I would also appreciate it if you could provide some basic driving directions to the trail head.
Thank you in advance!