Sailing to Hawaii
from SD is pretty straightforward and will be about 18 to 24 days for you of at sea adventure. I would not do it in El Nino years such as this year. Once you've sailed around the islands for a few months then making your way back is a trip north then hooking toward Oregon/Washington and coming down the coast (best done in late summer). If you do a search using the engine
after my signature for Hawaii you can find some discussion about sailing here.
If you prefer coastline and port hopping then heading south is better. I've not done that.