Double Towing with my rig (pics updated 5-13-2014)

empty, we have towed a boat behind our fifth-wheels since 1993 with no troubles. You just have to remember that backing up is pretty much not available with all three items hooked up. Other than that, you just have to be aware that it's a pretty long load and you can't turn corners sharp but you see that with 18-wheelers all the time so it shouldn't be much of a learning experience. Just make sure you have a well-attached hitch so your boat doesn't fall off the FW while you are toodling down the road.