Lets take the tow vehicle first. Your Tacoma has a MAX towing rating of #5000. However, it likely is the max A Tacoma can tow. Make sure it is the max YOUR's can tow. Usually manufacturers give out tow numbers that are for a 2 wheel drive (regular cab in trucks) with the biggest engine for that model line.
Example, I own a Dodge RAM 2500, their max towing is about #12000. However, I have the V8 hemi, with 3.73 gears, 4 wheel drive, and quad cab, so my max is #8800, if I upgrade JUST to the gears to 4.10, I am good to #10800. Anyway, just really look up the specs.
Ok, so lets assume you can tow #5000. that is package weight. Looks like a pre 1998 model Catalina 25 is at least #4150 displacement. So figure at least another #1500 for the trailer (probably more)... this is before you put anything like equipment, life jackets, motor, gas, battery etc. Dude, that is over your MAX tow rating assuming your truck is configured as their ideal tow vehicle.
Sorry... I'll be honest, my capri 22, at #2500, and probably #1500 trailer and gear, is pushing your trucks capabilities a bit, although others have managed to do it with a Honda Ridgeline, I think I'd consider that pushing it. If the trailer has good brakes (and it had better), and your engine is strong (toyota probably is), then you may be ok, but the package is LARGE, and travel at speed would be interesting, for sure.
I honestly don't have to think about it much, but I want you to see what I am talking about in size, so lemme show you my 3/4 ton truck (much bigger than your taco) towing a MUCH SMALLER boat 22 foot, and you tell me.
Now my truck tows the boat quite nicely, and a 1500 would likely too. But understand you need 4x4 to pull it out of the water (as 4 wheels are on the ramp at 20 degrees or so, pulling whatever weight the boat/trailer is) out of the water, on a slippery slimey ramp.
My shoal/wing keel, draws 2'4" and I know the cat 25 draws less in the swing config, but it's a heavier boat, and larger, and generally bigger all the way around, but without the tongue on the trailer extended my entire rear axle is underwater, and water is up to my bumper, to get the boat floating (I don't extend the tongue as the ramp is angled weird, and, the tongue would likely hang on the inverted angles).
Just some food for thought. I suspect a 22 footer is probably the largest you can comfortably tow. Towing is not just PULLING, most small cars can move something that big, it is handling on a corner, and stopping it.
Finally towing, is also tongue weight. Figure whatever number your trailer and boat package weighs in at, then take between 10 and 20% of that, figure that is weight on the back of your tow vehicle. Make sure all your empty weight of the tow vehicle, plus gear weight and passengers weight and that tongue weight added are substantially less than your GVWR of your tow vehicle. Don't know what that is? Look on the drivers door jam. One number will be curb weight, another will be GVWR (higher than curb weight, subtract one from the other and you'll get your max "hauling" number).