Woohoo! I just booked a 3-day weekend trip to Portland in late March. I'll be visiting my brother-in-law, enjoying the city and a little nature, going to some jazz clubs, looking at real estate investment opportunities and relaxing! I have been to Portland once before many years ago, also for a short vacation. I think I'm going to enjoy it more this time because I've grown to appreciate cities with good public transit and Portland is one of those cities. The light rail system, MAX, is well-known and within the Portland Transit Mall, there are many bus and rail options.
I occasionally listen to a podcast called Portland Jazz Jams which is hosted by Darren Littlejohn. It is about the Portland jazz scene and has interviews with local Portland jazz musicians and features recordings of Portland jam sessions. I'm hoping to have time to go to at least one jazz club and possibly see one of those jam sessions that airs on the podcast.