We have taken our boat to/from Anacortes and Gig Harbor four times this winter. For us it is a two-day trip and nobody has mentioned it but a great overnight or bail-out point is Port Ludlow just south of Port Townsend. It is well protected from most directions, has good anchorage towards the west side, and a great marina (UNLIMITED hot showers included with your moorage fee!). Perhaps best of all is the restaurant at the resort right at the marina, they have Black Butte Porter on tap and really good food
As far as the Straits, I have to agree with DelMarrey and others that timing the tides will be the single
biggest thing you can do to have a quick trip. If you can time the tides so you have an ebb leaving Orcas and catch the flood starting as you approach Admiralty Inlet, things will be much faster. We were doing over 12 knots over the ground through San Juan
Channel past Cattle Point! That said, if the wind is blowing decently from the south and you time a flood into Admiralty Inlet, waves tend to get steeper...
Two of our legs across the Strait (both southbound) were rough with winds pretty steady 20-25 on one and steady 25-30 with gusts to 45 on the other. The Strait wasn't too bad at 20-25, maybe 4' waves with slightly higher occasionally, but we got beat up pretty good on the other trip with constant 5'-6' waves in the Strait and 7' - 8' waves through Admiralty Inlet. With the wind from the south and trying to time a flood in through the Inlet, the waves get pretty steep and it just wasn't fun. On the other hand, since our boat is relatively new to us, it was a great learning
experience and our boat held up just fine. I found a few weak areas to address (like getting the anchor
firmly secured!) but would have to say, heading out on a brand new (to you) boat in anything over 15 knots will definitely present you with some potential challenges.
Last thing I can think of if the wind is blowing from the southeast (frequently this time of year). While Point Wilson and Marrowstone Point have earned their reputations for rough water
, on most of my trips I have to say some of the worst water we have encountered is along the east side of Marrowstone Island where you wouldn't really expect it. I think what happens is there is a lot of fetch when the wind is from the SE and it gets relatively shallow even 1/2 mile off the shore of the island. The waves don't necessarily get that much taller but really get steeper and have a shorter interval. That has been some of the most uncomfortable sailing we have experienced so staying out into Admiralty Inlet but just west of the traffic lanes would be my recommendation.
Have a healthy respect but don't sweat it too much, you will have a great time. Hope this helps...