Lots of really interesting suggestions here .. but maybe kind of missing the point ... The only truly cool way to tour Europe is to do it in what you already have .... buying a big budget car specifically for the purpose of posing at Stelvio is a little too contrived ... too much like self-proclaimed cool for it to work .... a Triumph Stag will look good but unless you already own it, it will have too much artefice for it to ring true .. a shepherd's Renault 4 on the other hand will look amazing ... true cool is about the unexpected in remarkable situations.....
So HW, buy a car that you love for the sheer thrill of driving it ... then take it to Europe, and by default, that will be cool ... and then you can avoid the "if only I had taken an X or a Y" ....
That said, large sunglasses and a head scarf for the lady plus blazer and cravat for your goodself is the only way to go .. ;-)
well said Speedbird
i ve just read 7 pages of this thread, and so far i have found, you want to spend under 20 grand on a chic car, drive around europe, then sell it when you return. you havent mentioned a budget for fuel, but seem to like a lot of the more uneconomical suggestions. so, how about a jensen FF? - luxurious, expensive enough to run for your