I feel going during special events is the best way. Food and Wine Festival and the Flower and Garden Show are great times. Christmas time is good, too. You have more activities at those times; so, you can get absorbed into all those events. There are lectures and parties to attend with those events.
Doing some special activities really helps like Lunch with an Imagineer at the Brown Derby. There are tours to do, as well. Keeping busy is a key for my enjoyment as a soloist. By the time I get back to the room I go to sleep.
If I get really lonely, I'll make a few calls back home. Sometimes, I have the courage to start up a conversation with someone else at the park and that helps some of the lonely moments. Some of the best times for this is when you wait in a long line or you are seeing a parade or fireworks. I want to get brave enough to approach another solo traveller at a table service and see if they want to eat together. The timing of it is crucial though; so, this is not so easy to accomplish. I like doing postcards to everyone and that helps the time back at the resort. Take pictures and video at the parks; this keeps you active and you don't think about being alone that way. Reading or doing your I-pad is okay, too.
I'm at a point where I either don't have people who can afford to go with me, or people who would have a hard time being there with all the walking involved (some will
scooter, some won't) or others who are just not that interested in going there. There are some who are just too lazy for a trip to Disney World. My hubby has been by partner for many trips, but his heart is not in it anymore. I know the day is coming where I will have to go solo more often or not go. I wish I could offer to pay someone's way all the time, but that's not to doable, either. I did it once when there was free dining, but it seems that free dining is not happening any more. I will say that trip was one of the worse; because, the person didn't really care about being there after the first day. They were more interested in smoking or texting or calling back home than being at Disney. Originally, they were eager to be there, but that wore out very fast. And it wasn't having me as a companion that made it unenjoyable; this person was just happier staying in the room and sleeping or watching TV. I still have bad memories about that trip. This person fooled me about going there and I won't do it again.
I will say I enjoyed most of the time on my solo trip, but there were some lonely moments. I do feel I prefer going with someone to Disney World, but I realize this will not happen too much in my future. I will say I rather go alone, then not at all. I think it gets easier to do it on each trip you take alone.
AAA has a special vacation package for solo travelers, now. It doesn't include Disney at this time. I'm probably going to try that sometime in the near future. Everyone is in the same boat and you will have activities to be together with other solo travelers and still have the opportunity to be on your own, too. I think AAA has recognized this as a problem and they are trying to address this issue.