>>1242959I don't think there's any reason to worry about canal and lock sizes unless you're in English narrowboat canals. Most canals have been built for commercial traffic and quite substantial ship size. Only issue might be mast height in some canals and navigable rivers, but sailboats rarely venture inlands anyway, their territories are large lakes, seas and oceans. As for the size, ocean crossings have been accomplished in sailboats as little as 20-something feet long, but for improved stability and adequate interior living space something at least about 35 feet long would be better, but even larger boots of 45-60 feet long are common for transoceanic voyages. If you sail single handed you don't want it to be too large either because the larger the boat, the heavier the sails for handling and raising.
Trailering ability depends on your local laws on maximum trailer weight and dimensions. For example here in Germany a sporty light 28 footer like the H-boat is already the heaviest thing you can trailer around on a regular car license without getting an additional large trailer license for another thousand bucks, and even then you'll be limited by beam (width) very soon unless you wanna get an oversize permit whenever you trailer your boat around, but I know things are different about trailer weight in the US, and possibly about trailer size as well.
