Flying Under the Radar
Join Date: Oct 2007
Location: Northeast PA
Bikes: 10' SuperiorLite SL Club | 06' Giant FCR3 | 2010 GT Avalanche 3.0 Disc
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First of all, there is no such thing as being TOO ambitious in life. Secondly do not listen to anybody who does not have at least some experience touring. So if you do take advice, ask where it is coming from for the most part.
Anyways, I did very similar thing where I just planned on a starting point and a destination without much of the details in between. I would hope you would like to be better prepared for the tour than that. However, there were things I would have never had the opportunity to see or do if I had chosen a solid route.
If you are with a group of friends, just make sure you will be able to want to kill each other but not actually go through with it. Because that is pretty much what will happen. Despite what kind of shape all three of you are in, there is bound to be a weak link who is going to feel worse the whole time.
I think your biggest issue here would be the international part. Crossing state lines can sometimes be tricky with Vehicle only toll roads and bridges. Crossing international boarders only makes things that much more difficult. Be prepared to have your stuff searched and questioned routinely.
Other than all that jarble, just Have Fun, Stay Excited, and Start Preparing.