Hello! I am also a single parent who travels alone with my DD quite often. My ex and I divorced before DD's 2nd birthday. I tried planning vacations with other people. I spent a lot of time doing things that I didn't want to do because I was a going along with the crowd. After a couple years, I decided that I was going to stop listening to everyone else and planned a solo trip. It went great and every trip since has as well. My DD (now 8) will be on the Sept. 16 Double Dip Cruise. It's our first cruise, but I think that it will be easier to do the cruise than the other vacations that we have done because I will have the kids club to help me get some free time.
You will run into situations that have to be handled differently because it is only the two of you. For example, if your DD needs to potty before you are finished with a meal at a restaurant, make sure you tell someone where you are going before getting up from the table. Several times, we have returned to a cleared table. This even happened at the Crystal Palace in Magic Kingdom, we were almost finished with dinner, but we were finishing off deserts, etc, and my DD needed to go to the rest room. I got up and took her. When we returned, they had cleared our table and seated another family. You'll find this same problem with loosing your seat at the pool, etc. Another problem that I run into quite often is having to gather all my things up and carry them with me every time DD decides she needs to potty,etc., because there is no third person there to keep an eye on things. Over the years, I have learned that only about 1/3 of what you think you need is really necessary. Wney on vacation, I carry a pack each day when out and about. If it doesn't fit in the pack, it doesn't go. When DD runs up and says I've got to go, all I have to do is grab one bag and run. You'll learn all the little tricks.
I have ran into only one problem with me traveling alone with DD that I have not yet found a solution for. She goes to bed hours before I do. This means that I either pay out big bucks for suits with separate day rooms and bed rooms (which adds up to several hundreds of dollars) or the lights and tv are off and I'm sitting in the dark looking at the walls. I still haven't found a solution for that problem.