Hello
If you commute daily in Parisian traffic you're about ready for pretty much anything!
I had about 6 months riding experience (about 2,000km) when I went on a tour of Ireland 2up with my girlfriend on the back (about 1,800km in 5 days). This was the first time I ever rode with a pillion on board.
I now have 2 years experience and about 8,000km riding under my belt. A lot of it 2up. We fly to Buenos Aires in 3 weeks to start a 6 month tour of the Americas. Again, we'll be 2up. I have doubts over the amount of riding experience I have, but what the hell, we're going for it. You only get experience by riding, no? You're only young(ish) once too!
The trips to Frankfurt and Milan you mentioned sound like the perfect trips to get used to long distance touring. Wish I could have done a few similar trips as preparation.
Hope this is of some use, if only so that you can tell your family that some idiot from Wales (with less riding experience than you) is going on a 6 month trip to South America with his better half on the back!
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