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Go back to San Diego. San Diego has some great locations within reasonable distances, and boats sell cheaper there. First of all, San Diego harbor itself, but within 10 hours is Catalina Island, and another 10 hours north of that, the Channel Islands National Park consisting of 4 islands in the Santa Barbara Channel.
May and June could be a bit iffy re weather. In May expect heavy N to NW winds, although there are some good days. June is generally overcast. The best month(s) is from August to sometimes through November. I've spent Christmas at the islands in shorts and sunscreen.
If you're new to sailing, hire an instructor to check you out on the boat and your skills. I'm not much for sailing schools, which are too pricey and usually try to charge exhorbitant prices for boats in their charters. An instructor will be half the cost and a lot more informative on a one-on-one basis. Yeah, yeah, won't get certified, who cares? I've chartered all around the world and never been asked for a certification.
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Just checking in. Where ya'll keep'n the wimmin 'round here?
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