Hey guys,
Great discussion here. Comparing a windsurfer to a NE Dory is extremely unfair. The Dory acts much more like a displacement hull and the windsurfer creates a ton of lift, which reduces wetted surface area/drag.
Laszlo as usual, has the right of things. The water between the San Juans is a washing machine. The turbulence of the tides, eddies, etc. destroys steerage which is a function of laminar flow over the daggerboard and rudder. Also, there is "canyon effect" which causes venturi nozzle consequences in some places and wind shadow, which is horizontally 10x the height of the island upwind from you. There is very little sailing between the San Juans. Now if you go South of them, then tack North, you might have a clear shot.
I have only skippered a flybridge power-cruiser (named Sea-Cup, owned by NautiGirl) to Roche Harbor. It was a slow, expensive ride, using lots of fuel to navigate around things like Obstruction Island (aptly named) and steerage was mushy to say the least.
IMHO, a trip from Anacortes to Friday Harbor may very well take a long day only if you take the Southern route, below the islands, which eliminates most of the scenery. Or, you can go between islands and take the scenic route, which would take more than ten hours under sail.
Please don't take any of this to say that it shouldn't be done/attempted. A good VHF, dry suit, proper water-activated lights (use SOLAS wherever possible) and some camping gear on board would make this an epic trip (think GoPro and YouTube). When I finish my Passagemaker, you will be able to find me on Sucia on any given Summer Sailstice.
BTW, here's a map I made years ago while living on Lummi Island. A lot has changed since then. For example, I now own a daysail charter company on St. Thomas in the USVI, where I may build a Passagemaker or Dudley Dix's Oppikat for my son.
