OK Irvin, I'll be the one to pi*s in the Wheaties, I know there'll be others if they read this thread.
If you plan to do a lot of two up riding, especially for long distances get something other than a Speedmaster or America.
Don't get me wrong, these are very cool bikes and I have ridden mine for long distances and others have ridden much longer. Some two up.
That said, it's underpowered for two passenger touring. Mine is set up as a solo ride for that reason.
Get a bike with plenty of power and comfort. The T-Bird may fit the bill. A Rocket Three may do it.
A SM/BA won't. They are not hod rods (of course money and time can make anything fast).
They are sweet middleweight cruisers that handle better than anything else in their class. They are more powerful than any size wise comparable bike. They are a blast to ride and look nice too.
Now if you have in mind an occasional two up putt around town, or even a day trip once in a while........well, I'd still want something stronger, but a SM/BA might be adequate.