I have towed my double trailer rig during the past 2 years in Louisiana and Texas.
In my case, I am max'ed out at 65 feet overall length.
No problem except finding gas stations where I can pull up to the pump without unhitching.







I have a wireless backup camera mounted on the rear bumper of my travel trailer so I can see if the boat trailer is OK. The mirrors don't show the boat trailer except on curves.

 

Bumper pull double trailer pulling is legal here in WI. I set up our old travel trailer to do it but never got around to pulling the boat. Set up our new trailer to do it also, but now we would be 70 ft long, longer than the states 65 ft limit. I bet nobody would ever notice, but I'm not sure I can take the chance.

 

Most of the older Flying J truck stops have an RV island just for your use. No problem with pulling two trailers thru those RV islands. Unlike the big-truck islands, the RV island has gas as well as diesel. I've filled up at the RV islands often while towing my 5er plus a 10' utility trailer that hauled a golf cart or handicap scooter plus gas, generator, and other stuff.

 

It's legal here only if the lead trailer is a 5th wheel but illegal for 2 bumper pulls.

Honestly here I think if a guy wants to do that they should have to get a commercial drivers license and take driver training. Most monkeys can't handle one trailer safely let alone 2 of them.

 

If my rig is illegal in Alberta, then I won't drive it in Alberta.
It's also illegal in 22 states. I don't drive my double trailer rig in those states.

 

I am pretty sure it is illegal across Canada period.... but you are in Texas so that's probably okay lol.

 

It's legal in Ontario for sure I have relatives that have been doing it for years. It's illegal in bc though which is a good thing cause everyone around here is towing 30 ft boats.

 

Legal in Saskatchewan to pull 2 hitch pulls. In Alberta the front trailer must be a fifth wheel. My dad pulls a 22' Hitch pull TT and a 16' aluminium fishing boat behind his 2006 5.4 all the time. Says it doesn't make a difference in handling with the fishing boat back there or not.

 

Same thing here.
I find that there is no difference in handling with or without the boat trailer.
I just have to swing a little bit wider on sharp corners.
Also allow more distance behind when changing lanes.

 

Yup same here in Manitoba, must be a 5th wheel to do that.