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What should I expect to spend annually in engine/general boat maintenance for a boat that is 2005 and 33'? I'm trying to get a gauge of whether buying something like this is within reach or I'm just dreaming.

Yes, that is one way but there is fuel available on the island.

I'm interested in a Sea Ray to be docked in San Diego and do periodic trips to Catalina which is 76 Nautical miles for my family of 4. What year, length and model do you recommend for this particular trip and just general comfort. I'm also unsure how old of a boat and hours I should buy such...