Don't start sailing!!! It is a life long addiction....
I race on two boats in the Columbia River and cruise on our own 26 foot sailboat.
If you are a sailor, or want to try sailing, the Columbia River is a great place for it. There is also sailing on the Willamette river, but mostly small dinghy style boats. Southern Oregon has Klammath Lake, the main spots on the Coast are Astoria and Newport, and Central Oregon has the cascade lakes (beautiful area).
Here are some links to Portland area Sailing
www.sailpdx.com http://columbiarivercatalina.org/ http://www.cycportland.com/new_page_2.htm http://www.willamettesailingclub.com/
Pictures of Columbia River Sailing:
http://www.sailpdx.com/pictures.html