We are looking at getting a 5th wheel camper nothing real big and expensive but nice.. we also have a 19.5ft fiberglass ski boat that we would like to pull also.. I have seen it done pulling 2 trailers but im sure they have to be under a certain length combined... I know every state has different laws and such Im not 100% sure about Minnesota though... any thoughts?

 

Here's a state by state listing of regulations for tandem trailers. Keeping in mind that this is just a guide and not an official legally binding document.
http://www.towingworld.com/articles/TowingLaws.htm

 

I know in NY it can only be done on the interstate, other than that... I have no idea.

 

Here in WI the combination cannot exceed 65' or 60' if the second trailer does not have brakes. It must go in order of weight and one of the must be a camper followed by an empty trailer or boat or trailer with a recreational vehicle on it. You need a special permit in WI which i think its like 30 bucks.

In MN. No permit needed, cannot exceed 70', trailer connecting to truck must be 5th wheel style and second trail must be for recreational vehicle. Cannot travel through the twin cities during rush hour.

 

Red, cant imagine trying to pull 2 trailers through the cities during rush hour... deffinetly be a nail biter!!

 

No doubt, Its just bad enough when I'm in my truck by itself!

 

First will the back bumper handle the weight that you want to pull? I am building my own hitch so I can pull my bike trailer but that is about 1600 LBS with bike and trailer.
2nd the longer the rig the larger turning radius and I have been a few spots with my 450 and 38 foot that tested my driving skills if you get cars siting in the wrong spots. As long a you use truck stops and large areas to maneuver go for it. I would think twice if it was me.