I live, work, and grew up in the Portland area.
Europe! Very specifically, I'd take a train ride through Europe, stopping at the specific places I'm interested in seeing, such as London, Berlin, and Memorial and Museum Auschwitz-Birkenau. ... See More
I prefer red eyes, but I can't sleep on airplanes, so my best suggestion would be something to listen to music on and a book, or even bring some audiobooks and podcasts so you can rest your eyes while you listen, which will probably earn you brownie points with your... See More
Price, # stops, and departure/arrival time. I depend on public transit, so I can't be leaving or arriving within a transit dead zone without making additional arrangements. I prefer to take late night flights and arrive in the morning after transit begins running. See More
Hawaii is pretty fun, but you're looking at a 3-hour time difference, which is the same as the Caribbean. Given that, if an int'l location is acceptable, I'd suggest Cayman Islands instead. I went there as a child and... See More