I've gone to WDW solo 5 times (with a 6th booked for later this year) and enjoy it as much solo as I do with family. I'm the Disney fanatic in the family, so I love going. If I can go with others great, if not, then it's solo. I have had people tell me "won't you be lonely", "why go solo there", and the best was "that sounds a bit selfish." What??? There is an incredible freedom going solo at WDW. You get to do what you want to do when you want to do it. You can dine where and when you want. You can go on an attraction 50 times (I've done this with the Haunted Mansion - it's my favorite) or skip some all together (I don't do Space, Splash, ToT or RnRC). The biggest thing is that the only person you have to worry about having a good time is you! I enjoy reading, so I always have a book with me, so that takes care of any awkwardness of dining alone. Now, even though it's Disney, I'm still smart about traveling solo. I don't wear or bring alot of jewelry (who am I impressing). I only bring 1 credit card, my license and my health insurance card. That's it. Less to lose. I am aware of my surroundings, always keep my resort room door locked and my valuables in the safe. If you want to go, then go! I have found I can do Disney on a budget and still enjoy everything. For instance, when picking a resort, look at everything the resort has to offer and will you use most of it? If you just need a place to sleep & swim, then one of the values is best. If you are looking for something a little nicer, than a moderate is best. My favorite moderate when I go solo is Port Orleans French Quarter. It's small & compact, so it's easy to get everywhere. There is only one bus stop and there is a boat to DTD. I have stayed at POR & CBR as well and found these way too spread out for my taste. Some of these buildings are quite a hike to the main pool & foodcourt. If you have any questions, please let me know.