Best advice posted above, but beyond that there have been a couple of old bikes that have traveled the world, if you can find their blogs they might give some insight into traveling on an antique bike. Yon, I think from Holland, I met in Ecuador riding a WWII Harley 45. He met a girl in Colombia and may still be there. (Colombian girls have snagged more than one world traveler so use care there) A 47 Indian Chief was around the world. And there was a model T Ford on the way from Australia to London when I was in Africa.
You have the first requirement to do this, time. Five years means you have time to wait for that part you need to get to you. The older bikes were much easier to make what you needed or fix broken parts than today's computerized makes.
I had long planned to take my '53 Indian on some major trips but it was very badly damaged in a fire January 2015. May be able to fix it again with many new parts but I am waiting for some legal battles over the fire to come to an end before doing anything with it. I have a side car for it, (not burned), and it was to be what I rode when I got too old to hold up a bike.
Have a great ride
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