Towing two trailer at one time

As for towing doubles, it's quite common here in the Rocky mountain states. I've had several rigs set up this way, all bumper pulls which require some attention to detail when initially setting up. I've towed both trailer and boat, and trailer and utility trailer with ATVs. The biggest issues I've had keeping inside the 65 foot total length limit, and no special license or indorsement is required here. When towing the boat trailer combo, I would launch the boat prior to hitting the campground as it made unhooking and moving the boat trailer much easier so I could back the TT into the camping spot. Backing both trailers up wasn't hard other than I had to use a kind of zig zag procedures since I couldn't see the boat trailer in the mirrors when the whole rig was straight. You also had to be careful not to run into traction issues trying to pull the trailers back up the ramp as boat ramps can be slick.

The above said, especially when doing doubles with bumper pulls you really have set everything up perfect so you don't get sway. Things can get away from you much quicker, and more violently with doubles than with a single TT.