Hi Patrick- we're 'newby' full time cruisers, but started with the same dream that you describe. We were living in West Linn when the sailing bug caught us. Learned to sail on the
Columbia from one of the Parks and Rec courses offered from time to time. One of the sailing clubs would also be a good option. In our case, we needed to get some experience in sailing prior to
purchasing our cruising boat. Financially, not owning a boat would have been better for us, but we really wanted to have our own. On the river, we had both a
Catalina 25 and a
Newport 30. We trailered the
Catalina to the San Juans for a bit more experience and
vacation. The
Newport was fine for sailing up and down the coast, as well as cruising up and down the river. We finally settled on a
Tayana 37 for our cruising boat... but for reasons that pertained to us. On the river, it is a bit of a pig, it takes a while to tack, and it really likes the
wind to get moving. In the ocean, it's fantastic. And for the last 7-months a great
live-aboard.
Rather than decide on a cruising boat at this point in time, you may be better off in developing your skills, and then look at boats that suit your style a few years prior to taking off.
We left the rat
race, and so far... no regrets.
Steve