I've had a similar problem, except sailing back and forth from Oregon, up to the Salish Sea of Washington and British Columbia. It has the added problem of being an international trip, further limiting the number of ports I can put into, not to mention the cold, rainy, iron bound coast of Washington with its poverty of ports, decent or otherwise.

I depend totally on crew. There's no way I'd try to single hand it (although people do) and my wife won't have anything to do with it. In the spring, it's easy because I race the Oregon Offshore (Astoria to Victoria), so there are lots of enthusiasts to choose from, and the schedule is driven by somebody else (the race committee). I leave precisely on the second Thursday of May and arrive (hopefully!!!) 36 to 60 hours later.

The return is tougher. I'm always cajoling friends, fellow yacht club members, people who think they might want to try offshore sailing,... anyone I can find. I try to accommodate schedules, but make it absolutely clear that the weather has its own mind.

I just got back yesterday from the annual migration. We had to wait 2 days at Neah Bay for a weather window. Fortunately, the crew was forewarned, so the pressure was off. Still, if I'd have had my way, I would have waited still another day for the predicted better winds.

Once in the past, feeling lazy, I left the boat up there for the winter. Except, I found I hated the driving back and forth even more.

Sorry, no real suggestions here, but I know exactly what you're feeling. Saturday night, midnight to 3am watch, it's freezing cold, raining, and I'm dodging fish boats and crab pots all night long and thinking, "There's got to be a better way..."

But, there isn't.

-tk