As far as Sailboats with a cabin, I think the winner would be the Catalina 22. They made a lot of them and they still are making them. This is without a doubt the most popular trailer sailor weekender racer that I've heard of. The still have a very active one design fleet as well.
Popularity must be defined. As much as I admire Catalina's it depends on what particular boat. I would think the C22 has more boats manufactured just because it smaller and cheaper (even knowing the popularity of the C30).And taking it a step further, I would think the "Laser" or "Sunfish" is even more prolific (popular is a relative term)
I heard somewhere that the most popular boat ever sold was a 26 footer. I cant even remember where I saw it or what kind it was! I was talking about small 20 to 30 footers, all fiberglass, and production models!
Here are some estimates-Sunfish 250,000 +Laser 150,000 +Hobie 16 100,000 +Catalina 22 16,000 + Catalina 30 6,500 +I think you will find that the Cat 25 and 27 will probably fit somewhere between the 22 and the 30.
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