The Seawind II is an outstanding cruising boat, perhaps the best in its size and price range...maybe the best in its size range, period. I disagree that the original Seawind is a better built boat. The Seawind II had the same layup schedule and corrected a number of problems in the original, primarily the leaky hull-to-deck joint.
As an ocean boat, I don't think the Pearson 323 compares. The Pearson is built as a coastal cruiser (i.e. screwed-on hull-to-deck joint). The Seawind II is a legitimate ocean boat. There are, of course, tradeoffs to be made in constructing an ocean boat. While it is possible to sail well in light airs, it is going to be a good deal more difficult in most situations. The Seawind II will not point as high as a typical coastal cruiser, either. And maneuvering in reverse is pretty close to impossible. That said, if offshore cruising is your goal, the Seawind II represents an outstanding value and is very well-suited to the task.
The Southern Cross 31 is very similar. Basically the same design (both by Thomas Gillmer), but a little smaller, cutter-rigged, and with a canoe stern. The Valiant 32 is another great ocean boat, but it will perform better upwind and in light airs. Pacific Seacraft Mariah 31 is also worthy of consideration. Baba 30 is a good cruising boat, but a lot of teak to maintain - sure looks nice, though. If you can go a little smaller, the Shannon 28 is an outstanding offshore boat as well, and it has significantly higher quality fit and finish.
Last edited by flashingbrine; 05-03-2009 at 11:46 PM.