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johnny-
I'd expect hiring a captain for two weeks, even at $100 a day (lowball) would run you $1500 and since you may be motoring all the way, conservatively $300? worth of fuel, plus marina fees every night or most nights...if money is a concern, it might break even or work out cheaper to have the boat trucked down, which would take just a day.

Going offshore should be faster and cheaper but that can mean waiting for a weather window, offshore prep, and other issues as well. Not that boats belong on trucks, just that if you have doubts or restraints on this, trucking may not be an unreasonable way to go.
 

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5'3" really IS a shoal keel, to most of us. Shouldn't be a problem for any company that transports sailboats. Would be a problem for any yoyo with a truck who calls himself a mover, but isn't insured or licensed for the job. Renting a real boat trailer for a keelboat? Wouldn't be easy.

Now if you can find a Chinook crew and convince them that they need a heavy lift exercise...
 
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