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I have done several solo trips, and will be doing another in early November. I find that i have a really good time because I can do the things that I want to do without other people to worry whether they will find those things boring. I do enjoy meeting up with other Disney fans (used to go the yearly December MouseFests from the old radp days -- if anyone doesn't know what I'm talking about send me a PM and I'll explain) and am planning to post here before my trip that I would love to meet up with other Passporters to do stuff if any are interested.
One other note: I have noticed that being by oneself at character meals can net one a lot more attention from the characters. (Pity? who knows) I was at one by myself with my camera, autograph book etc., wearing Mickey ears, and had a lot of great interactions with Mickey & Minnie both! If they see that you are an enthusiastic Disney fan, even as a single big person, they'll play with you. I even got picked for the old MGM Monster Sound Stage Show and had lots of fun doing sound effects.
“Laughter is timeless. Imagination has no age. And dreams are forever.” – Walt Disney
I love solo trips. You get to do what you want, when you want, as often as want and eat what, when and where you want. If you're not comfortable eating out by yourself make sure you have something to read with you so you're not having to sit and stare at the people around you while you eat. If you have things you'd like to do or places you'd like to eat but never have because the people you travel with never want to this your opportunity to do and eat where want.
Going in October. I have never been to the Food & Wine Festival so looking forward to that.
Question : Is it easy to get sit down diner reservations for 1 on the day or a few days before? I am trying to leave my schedule open so planning is quite different than planning for 6 in the past. Do they seat you on your own ??
I like travelling solo. Last my solo trip was to Canada. I've booked cheap flights to Quebec and spent amazing weekend there. I always buy tickets for sale to save more money on entertainments. Next my solo trip will be to Disney too!