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I used to live in Friday Harbor and have boated the local waters a lot. I live in Seattle now and have made the trip up in my boat a few times... Couple of things to think about...
1) If you've never been around the islands by boat, watch out for EVERYTHING. The tides in the PNW can drop 10ft easily, and that means there are tons of rocks at low tide around the islands. check your charts and give yourself plenty of clearance.
2) Once you get "inside" the islands, you will see tons of deadheads, kelp and other random things that get caught in the many tide rips. This stuff can be VERY hard to see at night. (In a sailboat I find this isn't as bad since you are going slower and most of the smaller stuff just slides along).
3) The weather and especially the wind can get very fluky. Because of the island terrain, you can get wind shifts and altogether fluky conditions... this can be a big PITA if you are sailing. Changing course could put you closer to the rocks I mention in #1
All of this though is very manageable if you think ahead and are careful about your route. I agree with everybody in the thread that the currents can be VERY helpful on the way up. The way I've done it in the past is to leave Seattle (Shillshoal) around 5am, catch the Ebb out to Admiralty Head, pass Port Townsend around slack (maybe just a bit before) and ride the Flood through Cattle Pass (don't do this at night though, it is a very tricky pass). doing this (with an avg of 5knots) I get in around 2pm. The trip (dock to dock) is about 60nm, so at 5knots your looking at 11hrs, but the current can cut that down by 2-3 hours easy.
One thing to watch is the conditions around Port Townsend. There can be a ton of fog. Also the waves can get pretty big if the wind is up against a good current. I screwed up the timing once, and went through PT at max ebb, against a north wind... make a 3-5ft sea just outside of PT... mix that with the VTS (3 main shipping lanes converge just outside PT) and it can get very messy!
I've never run up to San Juan overnight... something I'd love to try someday, but I don't know that I have the stones for it just yet... I'm sure you can do it, just be very careful! Good Luck!
USCG Master 100T
S/V Priorities (79' CAL 31)
Last edited by WhatTheFoley; 08-05-2009 at 07:35 PM.