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Hi and congrats on getting an Islander. I have a 1979 Islander Bahama and love it. I had a similar issue, but to a much lesser degree. I would get lots of leaks whenever it rained and was frustrated with never being able to find the actual point where the water was getting in. I finally used the ShopVac method you mentioned ( I actually used a heavy duty leaf blower) and it worked great.

The hardest part is getting everything sealed up without forgetting something you need that you left inside the boat or forgot to block off your solar fan, etc. Once you seal her up and blow the air in, get a spray bottle with soapy water and start spraying everywhere. I found a leak around a port window but the major leak came from the very bow of the boat between the deck and a plastic trim piece that goes around the bow between the toe rails. I filled in the space with silicone and it worked great.

Hope this helps. Good luck
 

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one last thought; don't forget that the ice box drains into the bilge (at least it does on mine). Make sure you don't have some crazy leak that's getting into the bilge via that route.

Good Luck.
 
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