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My riding consists of commuting to work 50 miles round trip and two-up riding on the weekend. I like riding in the canyons here in California.
Does anyone have experience with a few different bikes? If I am comfortable on my shadow riding two-up how would it be with an America? Would it be a good bike for long trips?
No problem at all for two-up touring on the America/Speedmaster! There are members (like Moe) who routinely make big rides two-up. I put close to 40,000 mi. on my 2002 America with at least 50% with 2 riders aboard. Heck I can't even tell she's back there most of the time. I did put the Corbin passenger pillion on though which is quite a bit wider than the stock pillion.
All the best with whatever decision you make.
Welcome aboard! 
Definition of Insanity: "Doing things the same way over and over and expecting different results."
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