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The very first time we went to Disney World in 1984 (I was four...so that was 25 years ago!!) we stayed at the Contemporary. The fact that the monorail went through the hotel was so cool to me as a youngest. I would just stand and watch it for a while go in and out (I also apparently wouldn't get on one that wasn't pink or purple!).
I don't know if they still have it, but back then they had a movie theatre there that showed a Disney movie (we saw Peter Pan which at that time hadn't had it's 'every 7 year run' yet so I had never seen it--remember those days when they all still came out in the theater???).
We went in February--that is REALLY the best time to go. It was cold (there are pics of me in sweats and a vest) but there were virtually no lines. Much to my parents' chagrin we rode "It's a Small World" 3 times in a row!
I went to Disney World another 3 times (1986, 1988, 1992) in October while my Dad had business but stayed off-site where his meetings were until...
2007 when I convinced my folks to go back there for my 'last Winter Break ever' while I was in my last year of Law School. We stayed at the Boardwalk Inn. It is across the lake from the Yacht Club/Beach Club. You can take a Water Taxi to Epcot or walk (it wasn't far) and they had bus service to all of the other parks and the Animal Lodge. I was impressed by the Disney bus system--very easy and almost always on time!
We loved the Boardwalk Inn; we had a suite that was very nice and it had a small kitchen in it so that we were able to buy some groceries (they had a convenience store on the Boardwalk; wasn't too expensive) to have breakfast in the room or a snack. The Boardwalk itself had a couple of cute shops and a very nice restaurant (The Flying Fish) that my Dad loved. My parents were always a little critical of Disney food from our first ventures and were pleasantly surprised by that restaurant as well as the one in the Animal Lodge that we went to (not the buffet, the other one; I can't remember the name of it). They were both fantastic! I highly recommend the Boardwalk especially if you don't have little kids who need to spend most of their time at the Magic Kingdom. We did all of the parks, but many times walked over to Epcot for dinner as the way you walk into Epcot from there was to be near all of the International restaurants.
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