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for me its not about being a real biker or not, its just that I bought my bike so I could ride it, not drag it around. Trust me, I'm the least intimidating person you're likely to meet, I couldn't intimidate Pee Wee Herman. (Right Uncle Larry? )
I'm kidding mostly, I understand there are good reasons to trailer a bike, I just hope to avoid those reasons as much as possible.
I just happened across this ... :>) I've met Keith and he's a great guy ... intimidating? No!
You may be able to remove the bags and posture the bikes in that trailer?
Wrap the bags up in movers blankets and tote them in the truck until arrival at the destination.
Make sure the steel horses are tethered using the frame and not the body.
Swingarm at the shock mounts and front fender mounts, not the handlebars and seat mounts.
Reason I mention about proper tethering is I smashed my front fender by using the handle bars and ratcheting down toooooo much and it was also not as secure as frame tethering.
Don't know if it's in your plans, but check out The Tail of the Dragon and the Cherohala skyway. Made this run last July and it was fantastic riding.
A heritage and a street glide will take up 16 feet end to end, a 14 foot trailer with V-Nose is probably 17-18 feet. I still think you can make it happen
I put 2 street glides in my 7x14 and have thought about how to get a 3rd in there. My conclusion is I wouldn't. It would be way to close on space and would make strapping all 3 down really hard. A few years ago we trailered 4 baggers down to Daytona but that was in a 8.5x20 and that was still tight.
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