Join Date: Feb 2006
Location: London, UK
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I've seen both boats, but have sailed neither. There is an Islander 36 for sale here in Portland that I've been on. I was impressed by the overall build quality, and that it had been to Hawaii and back, and raced. From a design and build perspective, I'd prefer it to the Catalina. From a "living aboard" perspective, the interior design of the Catalina would likely win.
The Islander 36 in Portland isn't priced high, but it does have some water damage and leaks. The cabin sole feels warped, for example, and there's water stains and water inside from deck fittings and possibly port lights. The engine is also looking tired.
If you look online, there's some good sources in California about the Islander 36 and how they've been restored, cared for, and raced. I get the sense it might be a fun boat to sail, but also capable of doing distance.