I flew in from DC this (Friday) morning at around 12. Since the convention doesn't start until sometime tomorrow, and it's my first time in Portland, I decided to wander around a bit.
First mistake I made was to take a paid van to the hotel from the airport. The paid vans take you anywhere in the city for a flat rate of $13. What I didn't know was that there was a "Max" station at the airport and one (literally) right next to the hotel. The "Max" is a trolley service that runs every 10 minutes, it's very inexpensive, clean, and safe. So take the Max, it'll save you a bunch of money.
If you do take a van, be sure to ask your driver for some tips on places to check out.
The Doubletree hotel is right next to a GIGANTIC mall. It's three stories tall and very big. You can find everything there, and the prices aren't too bad either. If you and your friends are hungry, I definitely suggest you go to the 3rd level of the mall and each of you can pick out exactly what you want from the dozens of restaurants. The tables for all the restaurants are in the center, so you can all eat whatever you chose to buy together. There is also an ice skating rink, and a movie theatre.
The Max is FREE to go from the hotel to downtown and back. It runs every 10 minutes in each direction, so just hop on, go somewhere, and you can come straight back to the hotel anytime you want. Don't hesitate to just hop on and get off somewhere in downtown and walk around a bit, pick up a map at the hotel lobby and it'll be impossible for you to get lost.
Do not plan to spend time in Chinatown! That time will be wasted. Portland Chinatown is nothing but a bunch of shady looking Chinese restaurants/bars and an adult bookstore. I didn't see anything there but places I would never consider having a meal at, and a bunch of drunk people. The city appears to be remodeling the whole area, so the street is torn up and everything just looks like a mess.
If you want to get out and walk around a bit, I strongly recommend taking a walk across the top level of the "Steel Bridge." You'll get a great view of the city and the river. The bridge does raise if a boat comes by, but there are two levels, and the top level does not go up unless the bottom level can't go high enough. I saw the bottom level go up and a bunch of people had to wait 15+ minutes for the boat to arrive at the bridge and go under. I was at the top level so I was able to pass over the bridge without having to wait. If you're crossing at the bottom level and you see it start to go up, turn around and take the top level unless you don't mind standing around for a long time.
Some things to keep in mind:
Avoid mob mentality!
There are many streets in Portland that do not have crossing signals. Pay attention and do not cross if cars are coming! You will disrupt traffic and will be risking your life.
Watch for bikers on narrow sidewalks, especially on the bridge. Neither you nor they will be happy if you get in the way of a bike and get hit.
Don't stay at the hotel/con the whole time, especially if you traveled a long way to get here, Portland is a great city and has lots of things that you may sometime regret not seeing.
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If anyone wants some advice or someone to hang out with, drop by the AnimeOD booth and ask for George. There's a couple places I'm thinking about checking out tomorrow, and it'd be much more fun if I had someone to go with.