Race Transalp (sorry, too late for this year, but...

...a suggestion for next year)
My brother is currently competing in the Transalp, one of his Summer highlights. I've only seen pictures and never went there in person, but the scenery looks just awesome.
Here the link:
It surely takes some cash, time, preperation, and last but not least some fitness. I'd fail meeting most of the requirements above, but some here might be interested.
Oct 6, 2014
That is a link to the mountain biking Transalp. There is also a road bike version for anyone who is interested: http://tour-transalp.de/news/
It is very well organised. Highly recommend. It fills up very quickly - so generally you need to sign up when registration opens in December.