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Welcome, Rusty. You've opened up a can of worms here! By offshore cruising do you mean coastal cruising (not long open ocean passages)? Or do you mean to cross oceans? I haven't personally sailed either the Islander 36 or 41 Freeports, but I have known owners. I've sailed on a "plain" Islander 36 (the more popular and ubiquitous non-Freeport version), and for the most part they are decent performers with nice accomodations. Definitley coastal. And if I remember correctly, you need to look out for keel bolt issues. The I36 Freeport is generally well regarded, as are most Perry designs, though I'm not sure if they are recommended for open passages. A more knowledgeable person here can answer that. And though the I41 Freeports have been all over the place, as sail boats they are known as, well, "slow pigs". Of course, dockside they are pretty fantastic for living aboard and entertaining. Contrary to traditional aesthetics and opinions, I actually think they (and their predecessor the Islander 41 Motorsailer, which I think was designed by Angleman?) are pretty cool looking. But then I really like the pilothouse look. I knew someone w/a Freeport 41 in LA that ended up putting stabilizers on poles port and stbd for sailing the 26 miles over to Catalina Island. He said the boat was indeed pretty slow, and rolled heavily in any beam seas. But he loved it nonetheless. Had another friend that took his Freeport 41 up the Inside Passage to Alaska and back many times. Loved his boat, too.
Lastly, I once asked John Kretschmer about the 41 Freeport, as I was at the time looking for a liveaboard, and he just shook his head with a grimace and said "Nah, you don't want one of those". But he was only referring to the boat's sailing ability. He acknowledged the nice interior and layout for liveaboard and coastal cruising purposes, though.
As usual, it comes down to your intended use whether or not these boats are good for what you want.
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"Always approach the dock at the speed you wish to hit it."
s/v VENUS
1978 North Sea 33 Pilothouse Cutter (Ta Chiao)
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