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?

Rooster24v's Sig:

1998.5 2500 4x4, 5.9 liter 24v Quad Cab S.B. SLT, Automatic (DTT Tranny!!!),HTB2 62/13 s.s. Turbo w/HX40 downpipe, Isspro Pryometer and 60 psi boost gauge, BD Low Fuel Pressure LED, Quadzilla Adrenaline, Airdog 150, Fireball 150's, Airaid BHAF, 4" MBRP Exhaust w/5" MBRP rolled tip, BD Intercooler Boots, 3.54 axle. Thanks Lukesdiesel!!

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

Uncle Bubba's Sig:

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99 Quad Cab, 4wd, Drag Comp W/Pump Wire & Boost Elbow installed, K&N Air Canon, MBRP exhaust, Belt Drive Lift Pump and bottom Bulkhead feed from the tank, Isspro EV Pyrometer, Boost Gauge, Fuel Pressure Gauge, DT Pro Fab Trac Bar, South Bend 13-1.25 Con O Clutch, Ranch Hand Bumper, Borgeson Steering Shaft, Black Silicone Boots, 2" Lift Soft Ride Front Coils, Solenoid High Idle Kit, Bilstein 5100 HD Shocks, Rickson 19.5 Wheels w/Hancoock Rubber, HD Maxx Link Sway Bar Links, Superlift dual front stabilizer, EGR Brakes Front and Back, RV275 Injector's, Blue Chip VP44, Prodigy brake controller, B&W Gooseneck hitch and more I can't remember right now. Not to mention more to come I'm sure.
374.2/846.7 at 30psi

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

MotorOilMcCall's Sig:

99 2500 RC 4x4 5-Spd - Quad XZT, Leveling Kit, 35" Nitto's up front/Pro-Comp's rear, Ranch Hand Bumper, PPE Lift Pump

98 3500 12V QC 5x5 5-Spd - 191 DV's, 370 EDM's, 4K GSK, 17* Timing, SBC 3850 Puller Dual Disk, Big Input Shaft - SOLD

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_Rattler's Sig:

03 Flame Red 2500 4x4 QuadCab Handshaker HO, Kore HP Kit, 35's, Smarty REVO, AIRDOG II 165, Techni Cooler, K&NFIPK, MBRP Cool Duals 6inch tips, GunSlinger Shifter w/ a broken BD short throw , SRT Inine 6 Hood, Jacobs Brake, couple other goodies

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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!