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The American Sailing Association and US Sailing organization both have a lot of good recommendations for sailing schools. Also, many local marinas and yatch clubs offer sailing instruction as well. So do many high schools and colleges.
There are many places in Portland to take lessons. It depends on what type of sailing you would like to get into. If you are looking at boats under 20' you can go to the Willamette Sailing Club down on Macadam near willamette park. If larger vessels are what you are interested in, there are several places along the columbia.
Come down to the Willamette Sailing club on wednesday nights for the races to see some of the fleets that sail out there. We are also having an Open House on the 20th and most of the fleets will have a boat available to look at or go out for a ride. I believe some one from the sail school will be there to answer questions.
If you have any questions feel free to shoot me an email.
I'd like to sail larger vessels, but small vessels would be fun and either way something I want to experience. Yeah I checked out the Willamette Sailing Club website. It sounds good I will check it out. What does it take to join the club? It sounded like it was a lengthy process.
You will probably learn much faster on a smaller boat, rather than a bigger boat. The smaller boats are much more responsive and generally you will do more on one than on a larger one, where the size of the boat can separate the functions.
The S-Dog is right. You would do much better to learn to sail on a 22-24-foot keel boat. They are stable, forgiving, and have all of the basic systems you will see on larger boats.
Some of the more popular boats to learn on are Solings, Sonars, Cape Cod Mercuries, J/24s, Colgate 26s. Most of these have the full set of controls that you'd find on larger keel boats, but are small enough that you'll be using most of the them on a single sail. The larger boats are often setup with the controls farther apart, and often will not need to use some of them, as they're often less sensitive to the conditions.
An excellent book to read as a primer, to give you a foundation before you hit the water, is The Complete Sailor: Learning the Art of Sailing. It is by David Seidman, and is about $15 retail.
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