The longest road journey I ever did was in 1997 when I worked on a roadshow for Xerox. This was just after the first digital photocopier ("The Document Centre") was launched and at this stage there were only three of them in the world, one being in Europe.
Xerox needed to train their engineers how to work on them and their sales staff how to sell them (they had several advantages over analogue photocopiers) and it was decided that the best way was to take the photocopier around Europe on a tour rather than bringing all the staff to the photocopier.
So I drove a Volvo F12 with a 45' exhibition trailer which gullwinged out on both sides, the interior was a mock-up of an office, and once inside you would never guess you were in a lorry trailer.
The itinerary was Geneva, Zurich, Vienna, Budapest, Prague, Warsaw, Moscow, St Petersburg, Moscow (again), Kiev, Bucharest, Istanbul and Belgrade, spending a week in each. Once everything was set up, I was only required on site for half an hour at the beginning and end of the day for start-up and shutdown, the rest of the time I just went sightseeing.
From beginning to end, the whole tour took 107 days, or three-and-a-half months.
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