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Do it. Do your homework, but do it. Do something. The key question for you is what kind of experience you're looking for. If you enjoy having a stable group to share lunches and dinners with and have someone else do all the legwork, by all means - use one of the tour groups. I can't speak from experience because we're usually not enamored of spending so much time eating - we'd rather be driving, getting lost, stopping in some random town for a drink or a bratwurst, etc.
Of course, we've developed some level of comfort because we've been in the area before. We did an "organized" Danube tour in 2006 which was a great introduction, but the big take away for us at the end was "how hard can this be?" We've been back every year since with our own plans and have had a blast.
We've driven a lot of those roads - mostly in Germany and Switzerland. We've saved some of Austria and Italy for 2019 (we try to synch up with the Nurburgring 24 hour races and the 2018 dates are too early to have comfort the mountain passes will be open).
The scenery is stunning. The Alps are amazing. The postcard moments are around every corner.
Did I mention, do it?
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1997 993 Cabriolet
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