Thought I'd add my 2p worth. I should start be saying I have no overland motorbike experience but have done a fair amount of cycle touring, I decided to take my test on a whim really as something to do when the Dr's told me I couldnt ride a bicycle anymore (and no I'm not that old). I come and look at this sight to have a bit of a dream but in reality some trips round europe will be the most I manage for sometime (first nipper on way). After passing my test I bought a BMW F650 Funduro for £900, then on its maiden voyage some tit ran into the back of me at a roundabout, eventually the bike was fixed but it took a long time to get my confidence up, I use the bike most days to go to work and the odd weekend ride. Its taken around a year before I feel all that confident on it. I reckon that had I got something more offroad ready it could well have taken me longer, the BMW isnt fast but is fast enough to keep out of trouble when I want to, big enough to allow me to look around and capable of scooting down the motorway at 75 with a bit of zip still avaialble if needed. What I'm trying to say is maybe get a bike that is cheap and capable on the road first before you get carried away with dreams, it will help get you confident and ready to go. Unless of course you are just going to pass you test and bugger off in which case I'm slightly jealous.
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