I was thinking of buying something like a cal20 in portland oregon for like maybe 1500. I bought a cal20 here in Honolulu for 1600 and had a lot of fun with that.
Then for about 2 months I could sail as far up the Columbia Gorge as I can, exploring the towns which are supposed to abe a blast in summer like the dalles and hood river, and then turn around and go to Astoria, anchoring at alot of little islands and checking out the channels and rivers along the way.
It seems like a good first cruise. Some navigation, but you're on a river, so it's not too bad. Plenty of towns along the way to restock and refuel, but also good nature, so I can hike and stuff.