Yeah I know it's January but back in November I took my first trip to anywhere, in this case it was Vancouver Canada. Some friends I had played World of Warcraft with invited me to stay with them in their city close to Vancouver and I worked up enough courage to commit to it. I have never been outside Wisconsin/Minnesota for travel and I haven't been on an airplane before so I was a bit nervous about the trip.
Most advice I got from friends/coworkers/family was that take offs and landings were the worst part about flying and not to joke with anyone at the airport and also to have carry on luggage instead of checking bags in. My nephew, and all my nieces for that matter, all live in Minneapolis and that was the airport that offered direct flights to Vancouver so I didn't have to worry about lay overs, plus I had someone that could take me to and pick me up from the airport.
About the only thing scary about flying was the first time the plane would bank into landing at the Vancouver airport, it was a bit disconcerting seeing the ground directly below my window When the plane landed it took awhile for my friends to find me too, they kept asking what stores/shops I was near and apparently they had about 20 Tim Horten's coffeeshops in the airport.
I stayed for 11 days but 9 of them it was raining out so we didn't do much outside, at least it was fairly nice temperature wise with it around 50 degrees, my friends said it only snowed about 7-8 times a year there and it always melted the same day.
Got to ride on my first fare bus and also the sky train while I was there, while they owned a vehicle they didn't like to use it unless they had to, Got to see the various sites in the area, went to a few malls/stores, walked around several parks, went to the aquarium they had in the area too. Would definitely go back, this time it would be during the summer though.