I have a USCG 50 ton masters license with sailing and towing endorsements and would love to help you bring your boat up to the gulf islands, however I don't really have any time available till next month
. I have sailed in the San Juan and Canadian Gulf Islands for the past 10 years.
It's a pretty easy trip, around 100 miles, and you should be able to do it in 2 long days. Be sure to plan for the tidal currents as they can be pretty fast this time of year.
The last time I did that trip we stayed at Port Townsend and crossed the Straight the next morning and entered the San Juan's through Cattle Pass.
For Peace of mind you could get Sea Tow insurance so if any thing goes wrong you can get help without to much expense Cost is around 125 dollars per year.
If you have any questions about sailing this area feel free to ask