This app was mentioned in 1 comment, with an average of 3.00 upvotes
Hello! I've ridden cross country on a ninja 250 and I traveled about 250-300 miles per day. If I can do it on that then you definitely can on a cruiser! You might be a bit drained when you get to cali though, it can take a lot of energy out of you when riding like that long term.
The US is a huge place and there is really no realistic way to say "take these perfect roads for the next 3,000 miles". I found the absolute best way is to get a good gps with settings that you like.
If you have an android, I really fell in love with this app. I tried many offline gps apps and this one really had the best navigation algorithms that picked enjoyable routes. You have to make sure the settings are for "shortest route" and highways "off". It will put you on local "highways" that get you going 55mph, but not interstates, which is what I hate (especially on a 250).
https://play.google.com/store/apps/details?id=com.skobbler.forevermapngusa
Anyways that is my suggestion! The app I suggested is not perfect and it makes stupid mistakes sometimes but its great 98% of the time, which is good enough for me as I don't have to spend dozens of hours researching and hand crafting a 3,000 mile long route! I used it exclusively on a 9,500 road trip and it never let me down :)