Siren’s Voyages
Hawaii is a great place to sail with a good variety of sailing conditions: Stay in the protected bays or pick a big day to practice those heavy weather skills. Join a weekly beer-can race or island hop for a few weeks. Hop off on a big adventure and ride the trades to Polynesia and back during the voyaging season.
Personally, my favorite is the interisland excursions staying off shore for a day or so, then hopping back to land for some kite surfing or snorkeling. Most anchorages are free on the way around the islands, some gloriously beautiful and some just a great calm place to sleep the night.
Slip fees are fairly reasonable, especially compared to California. But there does seem to be limited space, so be ready for a waiting list at your first choice. And as for live-aboard, be ready for an even longer wait. Or just anchor for free, moving your boat every 3 days to stay legal.
