OK, so here's my situation:

I'm currently in Houston, and my recently inherited '03 RKC is in upstate NY. I'm working on getting the bike here to Houston. Naturally the logical choice would be - fly to NY, enjoy many miles of fists in the wind. Not the case here. I also have to pick up my cage that has been in government storage for the past 11 months in Baltimore, MD. (Can't have the vehicle shipped here on the gov't dime due to my circumstances bringing me here to Houston. Short version, complications with my wife's pregnancy; not on official orders, just humanitarian temporary assignment)

Plan so far is fly to MD, grab the cage. Rent trailer (I know, I'm not too pleased with that prospect either). Drive to NY and bike up the bike as well as all associated equipment (lift, accessories, tools, etc.) I also have a buddy that lives in NC (it's on my route back here to TX) that had already been planning to come out this way on a trip to visit.

We have been tossing around the idea of making it a reunion roadtrip (we've been friends since we were in high school and haven't seen each other in about 4-5 years) where I make the run down to NC, and we load up his '13 Street Glide on the trailer as well and we cage it to TX (with him riding shotgun).

I had planned on renting a U-Haul 6'x9' trailer to haul the bike back with. What is the feasibility of that trailer accommodating those two bikes? If it will be a total no-go, what is the minimum size that would work? The trailer will be towed with a 2006 Jeep Grand Cherokee. I'd appreciate the assist; because if I had it my way, I'd be riding the bike back here.

 

I think 2 bikes will be pushing the capability of a Grand Cherokee. I used to pull a 5x10 trailer with an ATV weighing in the 800 lb range, plus some extras, with a 2004 Grand Cherokee. It really had to work pulling! Your talking 2 bikes and extra bike gear, I wouldn't do it. Think your going to need another option and with picking up 3 vehicles you looking at a big rental truck to haul the bikes and gear while towing the Cherokee.

 

I don't think you will get two touring bikes in a 6X9 trailer, not to mention the lift, tools, etc. Your Jeep will pull the load if you take it easy, don't push and check your engine oil each time you buy fuel. Been there, done it.
Ride on.

 

You will need to stagger the bikes or load them opposite ends front to back. Good luck.

 

Your Jeep's owners manual will tell you what your max trailer weight limit is. A brief internet search suggests that for a V6 it is a 3,500 pounds. Two bikes at around 800 pounds each plus a trailer may come inside that, so do some homework and you should be able to answer your question! Being in Texas you're bound to have the V8, which may have a much higher towing limit!