Different states have different laws with regard to tandem towing. California, for example, permits tandem towing so long as the overall length from tow vehicle to fifth wheel to trailer is no longer than 60 feet and the driver holds a commercial or non-commercial Class-A driver's license.
I have not towed double. I have checked into the idea and found that only about 1/2 of the states allow it. In many of the allowing states it is limited to the last unit being a boat. In all states their length limits can not be exceeded. Check with the states you will be traveling in. If they all say it is O'k then I guess you can do it. One thing to think about is adding a hitch to the back of your 5er. It is wise to make sure it is attached to the frame not just the back bumper. Most 5er bumper are not strong enough for a hitch. It may change pin weight and affect the handling of your unit. You should stay within the weight limits for your truck. It would be a good idea to have atleast surge brakes on the motorcycle trailer. One thing to remember is that to back up you must unhitch the motorcycle trailer. Cornering will be somewhat different. Check with your insurance company to be sure your policy will cover the combination. Good luck
You canot see your bike trailer behind your 5er. Now our trailer has a plastic rear bumber,plus the trailer has a full belly cover(You can't see the frame). The big thing your bike could come loose and you would never know,until you stopped and no HOG on the trailer.
Clem 1999 3500 Dodge diesel 5sp 4:10 Edge Plug and play 4in Ex,EX Brake 38ft Avion Winter in South Texas