Can I do this?
 

2001 36' Bounder pulling '99 Durango, pulling a 20' Hewescraft Jet Boat.


Even Brake for the Durango, surge brakes for the boat.

personally, i wouldn't......but i have seen those setups.............

Stranger-

The brochure for that coach (link here) has the following specs:

GVWR: 20,500 pounds
GCWR: 25,500 pounds
Hitch Rating: 5,000 pounds horizontal, 500 pounds vertical

A label on your coach should confirm (or not) these values.

I expect you would exceed one or more of these ratings if you attempted to tow the truck and boat trailer at the same time.

ln addition, double towing like that is illegal in a lot of states as well as being over the 65' limit. Double towing in some states is allowed IF the first tow is a fifth wheel trailer and not a bumper pull. Here is an article that explains some of the ins and outs of multiple towing.
https://rv-roadtrips.thefuntimesguid...triple_towing/

Is this a gasser??

If its a Ford F53, I'd be concerned with transmission temperature. Early model V10 / F53 didn't have a engine coolant / transmission heat exchanger built into the radiator (year 1999 , 2000).

Its easy to check, see if the transmission fluid lines are attached at the bottom of the engine radiator. If they are, then the transmission fluid is cooled by the engine radiator.

Can you? Yes.
Should you? Absolutely not. You're definitely going to be over the 65 foot overall length limit (less in some states). You're also going to be over your weight ratings. That is not always a problem from my perspective, but in this case it's just more of a reason to not do it. That boat is going to be really unstable and hard to notice until it's way too late to do anything about it.
Can you drive the Bounder and have someone else drive the Durango with the boat? That seems like a much better idea if there is another driver available.

If you do, please let me (and everyone else) know so we can stay off the road. I sure would not want to be in front of you when you try to stop.

Skip Y
2010 Journey
Loc: Mich

I've seen it done in MI & S.D. Crazy!

You cannot do this in Michigan. As was stated before, first towed must be a fifth-wheel. Here is the law from Mich.gov:

A "recreational double" is a pickup truck pulling a fifth wheel trailer designed for recreational living purposes, with a second trailer attached to the rear of the fifth wheel trailer. The pickup truck must have a towing rate equal to, or greater than, the total weight being towed. To operate a recreational double, you must have an "R" endorsement on your driver license. Anyone age 18 or older with a valid driver license may apply for this endorsement at a branch office. A knowledge test is required. There is no skills test. Drivers holding a Group "A" CDL with a "T" double or triple trailers endorsement can operate a recreational double without the "R" endorsement. Triple trailers are not permitted in Michigan. For more information, obtain a copy of the brochure A Recreational Double Endorsement at a Secretary of State branch office or from this web site.