Sailing Options / Times / Routes to / from Seattle to Mexico / Hawaii / Tahiti

[sundowner]

What are the best options/routes/recommendations for sailing from Seattle area to warmer destinations (South or West) for the winter (leaving in October) but still be able to safely get the boat back up to Seattle by late spring? I'm looking to spend the winter crusing or in a warmer/milder climate and won't be able to leave from Seattle any earlier each year than October and will need to have the boat back north by May.

I could possibly have up to 6 or 7 months to cruise each year (Oct thru May) and was thinking of either heading to Hawaii/Tahiti and back or down the coast to Southern CA or Mexico (Baja or Cabo). I might be able to choose different routes/winter destinations for the next several years, so need to know what's possible/realistic and not too overly abitious for this amount of time in a nice 54' bluewater Ketch sailboat.

If you had 6-7 months to winter a boat somewhere in the PacWest area each year, what would be possible/recommended for various routes/directions to head? How difficult would it be to get the boat back up to Seattle in late Spring from either Mexico or Hawaii/Tahiti and which route would you take and what time would you leave to get back to Seattle by May?

Thanks,
Jeff