While driving home from work today, I saw a 57'ish Cadillac convertible pulling a small boat (18'?) that said "Cadillac Boats" high on the gunwale near the stern. Outboard eng was a 25hp Buccaneer and appeared to be of similar vintage. My first thought was that maybe GM made the boat but after a bit of searching the web, discovered the boats and cars were not related. They both appeared to be recently refurbished. The combo was turning a lot of heads.

The Cadillac script looked very similar to what GM wound up using later and there was some litigation between the 2 Cadillac's as noted here:
https://jalopnik.com/there-was-a-cad...ats-1699540448

I had never heard of Cadillac boats. Anyone remember these Cadillac boats? Were they decent boats? How rare are they?

Friend had a 12 foot fishing boat that was a Cadillac.
The company was based in and name comes from Cadillac MI.

History about the company here: Cadillac - Classic Boat Library

That's got the boat.

The Buccaneer was a product of Gale Outboard Marine which was a part of OMC. Back in that era there were more boat and motor manufacturers than you have letters in the alphabet. Sears and Montgomery Ward both had their own brand of boats and OB motors to push them, sold them right out of their department stores. Hell when I was a kid we had a Chrysler runabout with a 55 HP Chrysler outboard.

Cool picture! Too bad the sun was not out so the top could be down on the Caddy, perfect nostalgic day trip to the lake.

Haha Chrysler outboard..... they couldn't make a car that was reliable in the rain, so they figured they would make an outboard engine!
I see them every now and then and think of 70's era Chrysler's with a glove box full of spare resistors

Our Chrysler Marine dealer was only a couple miles up river from our summer cottage, service was easy. Being the first born in the family, and naturally the smarter one, I dumped that pair off on little bro and took over operational ownership of the Glastron with the Merc. Then at the age of 13 I bought the first ever of my very own boats. With a short term loan from the Bank of Roy, my dad, I purchased a gray and black metalflake Checkmate MX-13 with a 55 Merc, truly one bad azz boat! The start of a lifetime of dumbazz investment in pieces of fiberglass. Many decades later I am now sinking my Social Security checks into these 525's, does a man never learn?

Lots of inboards and I/O's were Chrysler back in the day. Chrysler Marine was huge until Chevy/Merc took over.