Can my truck pull this?

[Skunksmash]

I got a pontoon boat for me and the wife and family and friends to enjoy. But I have a few questions about pulling it. I don't have a newer truck, all I have is a 1987 Chevy Sliverado 5.7L 2wd automatic. I love my old truck, but I'm not sure if the old TBI 350 is up to the task. It still has some grunt, don't get me wrong. But the truck is 28 years old. Gotta cut it some slack due to its old age.

Its a 22 foot all aluminum boat, with an aluminum trailer. Should I even attempt this with the old truck? I haven't yet. I pulled the boat home from the dealer with a buddy's newer 2014 half ton gas truck that he let me borrow. The boat dealer was 50 miles away and I didn't want to chance it with the old truck before I got a chance to test it under much more comfortable and safer conditions. Didn't really want to break down and get stuck so far away from the house.

Thoughts? Opinions? The 22' boat isn't the biggest thing out there, but it isn't exactly small either. It made the new truck squat down a bit, so I can only imagine what it might do to my old chevy. And I don't want to tear my truck up, that's the last thing I want to do. And if it can pull the boat without any problems, should I get a self leveling kit or some helper springs? I just know its going to make the truck squat down even more than that newer truck.