Hi all! Just wanted to put in my two cents even though I'm kinda late for the topic. I had contemplated going on a solo trip about last year. I had my dates set for December 2012, then it changed to June 2013, and I finally did go in August 2013. It was awesome!
There were pros and cons to going alone, but I don't regret any part of my trip. Traveling was the worst part of it all. I think mainly because you aren't surrounded by the magic. Doesn't help I almost missed my flight home from Atlanta because I didn't have enough time between flights to get from one part of the airport to the other.
I did mostly keep to myself, but had talked to many other people throughout my trip. Mostly cast members, but there were a few others. It happens when you least expect it, but most of the time when you're waiting for something. Most of my encounters were while waiting for Wishes to start and I had some pretty interesting conversations with others. And if I didn't talk too much during the day, I called my mom at home to say good night, lol.
Dining alone was a bit awkward too, but really didn't have a problem with it. I didn't do any table services, even though I wanted to. By dining at off times of the day I sometimes had an entire area to myself to just sit and eat, play with my phone, or go through pictures on my camera. I often didn't even take time to stop and eat. Some days I didn't even watch what I was eating and spent most of my meals at window counters getting ice cream sundaes and dole whips, lol. That is my idea of a good meal
Rides weren't bad, I avoided a few that would be awkward riding with other people, like Test Track. But some were very fun alone and with others. One attraction I enjoyed alone was Kilimanjaro Safaris, I visited that about 5 times one day and got some of my best photos taken on it ever.
I loved being able to do whatever I wanted. Went to rope drop every morning, played myself out then went back to the hotel for a nap, shower and change of clothes before I was back in the parks. Each night I debated doing Illuminations, Fantasmic, or Wishes. So, one night of my trip I had seen Illuminations from Japan which wasn't not crowded at all. Every other night of my trip I was at Magic Kingdom for Wishes. I love fireworks, and photographing them too!
I really wanted to meet some characters, but I was a bit hesitant about it. One night, it was around closing at Magic Kingdom and I wandered through Storybookland Circus. I wanted to see the new Minnie, Daisy, Donald and Goofy. So it said a 5 minute wait and I went in. Talk about weird...No one was there except for about 8 cast members and the four characters. They took my picture with them all and I hopped from one to another. It didn't go on without a show though. Daisy was trying to make Donald jealous when I was with her, and Goofy kept picking on me, and tried to steal the lens cap from my camera. Then I played follow the leader with Donald until he collapsed against the wall, panting. A cast member asked why he was so worn out, and he replied through gesture that it was because of his big backside. It was hilarious, but a good time.
Overall, I'm glad I went alone, and if I can afford it I think I am going to plan another one soon. So just do what you feel you can do and go. You'll have a great time, just don't be afraid to do it. There are a ton of nice people to chat with.