These weekend land trains are a more common occurrence these days, as pickup trucks become more capable and towing accessories more versatile. It’s also known as “towing doubles” or simply towing two trailers.
Different states have various laws that allow and/or prohibit such recreational towing. Several state limit the total / combined length of the truck and trailers. There are also other regulations that state only a 5th-wheel trailer (or a gooseneck) can haul an additional trailer behind it.
It definitely takes major skill to hook such a rig properly and drive it safely. Both trailers must have functional brakes. In this case, the boat trailer is likely to have surge/mechanical brakes (instead of electrically activated). Still, both trailers must be wired for lights to be legal.
Making a tight turn or backing up suck a rig is a whole other story. Please let us know your experiences with towing two trailers. Please share any stories or lessons learner in the comments section below, or my sending it to us at firstname.lastname@example.org