Time of year makes a big difference
When do you plan to make this trip?
When Late July and August rolls around the conditions in the afternoon can become pretty blustery. On top of that there is the fog to contend with.
If you're going shortly, in the next several weeks, my preference would be the Port Townsend route with some caveats.
That's a nice map you have with the optional routes shown and you're probably the first person to take the time to put something like that together that I can remember. Thanks!
Okay, here are my thoughts:
Currents: GO WITH THE FLOW !
Pick a few days with large tide swings, preferably minus tides. We're just going though some right now so it'll be another month until they return. June 15 has a -2.9 at Port Townsend and -3.2 at Seattle. On this day the slack before ebb is at ~4:50 AM with max ebb at ~8:30 at Tacoma Narrows with a current of 4.6 knots. If you were doing 6 knots through the water this would mean you'd be running at 10.6 knots over the ground. WoW! At this rate you can cover a lot of ground.
The next opportunity for something like this is around July 13 when there is a -2.5 ft tide in Seattle and a fairly good chance of fog. In August you can probably count on fog for sure.
After passing the Narrows take Covos Passage - the current always sets north and keep to the east side of center channel for maximum kick.
Slack before flood is at around 12:30 so you want to be in Kingston or Seattle by then.
To make this passage, though, I'd actually recommend starting, ideally, probably on the 14th so move everything up about 50 minutes and the Narrows current max ebb is 4.5 knots.
Unless you have some important reason for going to Seattle I'd skip it and go to Kingston instead. It is possible to anchor out but the ferry wake will rock the boat and there are a number of resident boats anchored out. Their marina is probably cheaper than Seattle.
On the 16th the ebb starts at around 4:40 AM (because you're in Kingston now) with a max ebb of 4 knots at Bush Point around 9:10 AM. Slack before flood is a little after noon. If you get stuck with fog and have to leave latter then take the back way to the west of Indian Island.
Interesting Point: If you can get past Foul Weather Bluff before the flood starts then you can take the cut to the west of Indian Island which will be flooding!!! Bridge clearance will not be a problem at this minus tide. Another free ride! Now you're talking Olympia to Port Townsend in ONE day!
Strait of Juan de Fuca Crossing
In June I think this would be fairly easy. Leave Port Townsend on the ebb then make the crossing. Leaving early in the morning there would be a good kick out to mid channel then catch the flood up the Strait of Georgia.
You'll have to make a customs and immigration stop somewhere and there are several places where you can do this so this will be a bit of hold-up. If you've been motoring and need fule, Cadboro Bay is a good stop (easy in-and-out and not too busy) and you can call Customs from their dock toll free. After that there are lots of places to anchor out.
By August the winds can become pretty nasty in the afternoon, especially on the Oak Harbor side. I personally don't like the Cattle Pass entrance because it seems it is nearly always very turbulent and bumpy and would not want to do this in the afternoon. The trip through the San Juans, if you're trying to make time, will probably be a motor-boat show. The Port Townsend to Cadboro Bay run, on the other hand, will probably be easy sailing after around noon with mostly wide open water and few hazards.
Please let us know when you are planning to make this trip.
New Narrows II bridge under construction
Strait of Juan de Fuca Center Channel buoy on a rare very calm day
(As shown on the map for comparison/reference, last summer I sailed from Olympia to Gig Harbor in an easy 7 hours.)
