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.