If it is not too late to contribute to this topic, some years ago there was a marvelous website developed by Scott McClintock, the designer and builder of the Rio Hondo 40 trailerable sailboat. That one was a racing machine, specifically designed for the Mackinac races, but it was also cruised on different waters across US.
I found the whole story for the first time in the April-May 2008 issue of Professional BoatBuilder (no. 112). The article was named "Maximum trailerable sailboat, minimum hassle", and from that moment I started dreaming about a home-built performance trailerable sailboat (back then I had plenty of leisure time to dedicate to the boat building hobby).
Later on mr. McClintock published a lot of technical data on the "Rio Hondo Yachts" website, and also the building plans for the Rio Hondo 40 were advertised for 500 US dollars. The photo gallery of the entire built was also on the website, and mr. McClintock expressed his intentions to develop 2 more trailerable boats, one cruiser of about 37', and another one I don't remember.
Unfortunately, a few years ago the website disappeared from the web, possibly because of the low demand, and the only refferences that can now be found are:
- mr. McClintock's blog -
Maximum Trailerable Boating: The Trailer Sailing Challenge http://maximumtrailerableboating.blogspot.com/2009/06/trailer-sailing-challenge.html ,
- the article on PBB, which can be found here (issue 112, page 22):
Professional BoatBuilder Back Issue Archive https://pbbackissues.advanced-pub.com/
- one discution about Rio Hondo Yachts on Sailing Anarchy Forum (I don't want to violate any rule here, so I can not put the link).
The idea of a 40' trailerable racer-cruiser monohull sailboat still makes me dream, even if my time is limited now. Such a length, combined with the small beam - 8,6', could make it a really fast boat, and the off-season problems are solved by keeping the boat on it's trailer. Today one could easily find a pickup truck to launch or retrieve the boat, it's not necessary to own a pickup truck.
This is the most interesting "maximum trailerable sailboat" that I know about, and it will keep fascinating me for the future.