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Switching to another boat (maybe)

If you're thinking about sailing to Hawaii, and then continuing on, I have a suggestion..look for a cruising boat in Hawaii.

I took a Santa Cruz 27 over in 2008 and while it was small inside for a big guy like me (this was before my Highland Games days, I was more like 230 pounds instead of 295) it was a great boat for the trip. I put the boat up for sale on Craigslist before i went and I had about ten serious replies. There's a Santa Cruz 27 fleet split between Honolulu and Kanehoe. You'll likely be able to sell it when you get there, even if you take off a bunch of the required gear, that you'll probably use on a cruising boat. You'd be taking to the boat to someplace where there's already a fleet, and that's a good thing.

SHTP is in June/July. But the optimal time for leaving Hawaii in the south Pacific, to avoid hurricane season, is October/November. So you could sell the SC27 and pick up a cruising boat in Hawaii, and have 3-4 months to prep. If you get a boat with "cruising experience" then there might not be too much to do.

Right now in Honolulu on Yachtworld, I see a Clearwater 35 for sale.
https://www.yachtworld.com/boats/1988/holby-clearwater-35-3700040/

That's a performance cruiser with an extremely stout lifting centerboard so you can get into some pretty skinny water, like anchoring close to the beach in tropical atolls.
 
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