-The Plane Trips
I'm probably an anomaly, but I usually take Amtrak or Greyhound, instead of flying - all the length of a car trip without the fun! I usually try to get an overnight itinerary - I can tell myself "This way you'll get some sleep before the con," but I never do...
Speaking of road trips, the best part is stopping at Walmart somewhere along the way and blowing all your dealer's room money on cheap food and electronics - I actually bought an alarm clock once, knowing full well the hotel room would have one. But this one had a CD player...
-The Hotel Stays
Sometimes, I'll intentionally look for a hotel away from the convention. Take Animazement - I stay at a suites-style hotel about a five minute walk away from the con. The rooms have microwaves and refrigerators, so I save money on food. The walk is really cool, especially when the weather's nice - you cut through this really cool office park that is dead quiet (Animazement's on Memorial Day Weekend, and all the salarymen are out of town). It's like there's nobody else in the world, and I can meditate on the way to the con. And saving $70 bucks a night means more plushies!
-what usually happens at a con?
Lotsa variables there. The fundamental events are the same - AMVs, cosplay, Dealer's Room, guest panels, and, of course, anime showings. Beyond that, it's case-by-case. Different cons have different special events, from Mystery Anime Theater 3000 at Otakon to AX Idol at AnimeExpo to various incarnations of Iron Chef (Artist, AMV Editor, Dorm Chef). Big cons are worlds different from little cons - more time is spent standing in line, for example. If you're going on your own, you'll probably wind up doing different stuff than you would if you're with a group. The area around the con is something to consider - you might spend more time away from the con if there's alot of other stuff going on nearby.
With that being said, a typical skeletal schedule would go something like this:
Friday morning - registration. Don't plan anything else during the morning, since registration can take a while. Many cons don't schedule events until the afternoon, anyway.
Friday afternoon - Dealer's room, anime screenings, panels. Most people at the con all weekend will try to hit the Dealer's room once it opens, looking for rare items and to avoid the Saturday crowds.
Friday evening - AMV contest. Would you expect anything else?
Friday night - free skate. Some of the stuff that's available - raves, room parties, bizarre and unusual anime, fan parodies. It depends on the con.
Saturday morning - what, you're up?

Actually, this is the time to bust out the camera - there'll be the most people, and the most people cosplaying, on Saturday.
Saturday afternoon - free skate. Fanboy/fangirl to your heart's content. Good time to check out the Art Room and Artist's Alley.
Saturday evening - Cosplay competition. This is always the biggest draw, so be ready to stand in line.
Saturday night - The Dance. Drink lots of water! Some cons also run all night video rooms, where you can watch a complete series in one sitting.
Sunday morning - This is the wind-down time. See things you haven't had a chance to see, make one last Dealer's room run, check out the Art Auction, where you can bid on original anime works.
Sunday afternoon - Make your farewells, but fret not, there's always next year!
OK, that's not very skeletal. How 'bout registration, dealer's room, anime, AMVs, rave, party, sleep, take pictures, art room, cosplay, dance, anime maration, sleep, wrap up, check out? Oh, eat should definitely go in there (more than once) somewhere.
Whew, sorry for the crazy long post. I've been going to cons for a long time, and (obviously) I don't mind talking, but I'll have to post my stories (including the time a half-asleep congoer got up in the middle of an all-night marathon to take a leak on the plant in the corner) at a later time.
Peace.
CPFuller