I have actually watched a gm 2500 haul the 55 mti down the street. they were only going 5 miles but it seemed to do fine.
I moved a 42' cat a few miles with a ford ranger once.

So im with the other guy, it depends on how far and why you are moving the boat. and there is a big difference in weight of different style and brand of boats,
Trailer design and setup has a lot to do with it also.

If I needed to move a 40' boat up to 20 miles I would move it with that truck. The tow rating is low on that truck because of engine size not being able to haul weight up a 8% grade in a mountain. so where you are hauling makes a big difference.

someone will get on here and say that if you are hauling 1 lb over the limit the truck tag has on it that it is dangerous and that they are mad that you might be hauling down the road next to them with there family and you will crash and kill them.

What I will say to that is I depends on the driver. Some people if it was a diesel dually hauling a jet ski I would not want to drive with my family on the same road as them. But there are other people that I would be fine driving next to going down the highway at 75 with them towing that 55 mti with your truck.

Had exact same truck but a 2000. Towed my 32 Fountain all over with zero problems. I'd loose speed on long hills but otherwise did just fine. Always towed with OD off to keep it from hunting and the RPMs up in the torque range.
A lot of opinions vary due to what THEY perceive as acceptable or not. I now have the same truck with the V10 and I don't see that much of an improvement over my 5.4

I have the same set up except in a F-150 and i'm pulling a Sunsation 288 i dont tow long distance execpt for usually once a summer to a poker run within a few hunderd miles, otherwise its 1 mile downt the road to the ramp. I can tell you with the 5.4 it will do it but once you hit the smallest incline it drops fast! Where i lauch the ramps are fairly steep and i have to drop all the way to low gear and put it into "4H" if the ramp is really steep. I think my 288 is 4400lbs and maybe 1500lbs for the trailer. If your like me and the truck is paid for you can make it work just use caution and make sure your trailer brakes work.

Yeah I think I saw the same guy in the dually pulling a jet ski. Oh yeah its paid off. That's kind of what I thought it would be slugish up hill but truck wise would be capable of a 29 if I just take it easy. I figured I'd have to use 4X4 on a steep ramp but I think I can work through that. Thanks again for all the input. US1 really can't see much difference between the 5.4 and V10??

There is some difference just not a huge one as I hoped. The v10 will tow at a lower rpm and in OD. I still loose speed going up long hills. Got better MPG with the 8. Both trucks 3:73
The difference between the 8 and the 10 is no where near the difference between the 10 and the desiel IMO

Your only going short distances? The 5.4 is a weak engine (I had one). But you could easily tow something like a 35 Fountain. I have dragged my 33 with a 1500 GMC and a 1500 Ram with zero issues. No brakes on trailer at the time. My buddy tows a 37 OL with a 1500. There was a Topgun transported recently from Miami to OH with a 1500. There is a guy I see every year that toes a 29 Outlaw with a Trailblazer.
Buy what you want but be safe and use your head.
Now some asshat will post you can't tow anything bigger than a runabout without a CDL and a Freightliner. Wait for it.......

. Yeah the difference between the 10 and diesel would be huge. I had a 99 crew cab F-250 with the 7.3 when I worked on the farm but when I got a different job I sold it and kept the gas. The gas pulls the horse trailer just fine didn't figure I need the diesel anymore till now........... Asshat that's really funny