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If we decide to purchase our tickets in the lobby on arrival day, can we add the dining plan for the length of the stay or does the dining plan have to be purchased before arrival???
If you purchase tickets at check-in, it sounds like you would have a room-only reservation and not a MYW package. If you want a dining plan at all you will have to book a MYW package (unless it is a DVC reservation). With only a couple of exceptions (annual passholders and the military room discount) you must add tickets when you make it a package, which would mean you would be buying the tickets ahead of time and not at arrival.
Even if you could you might not be able to get into any TS unless you are only considering the CS. You are really much better off figuring it all out ahead of time and purchasing the appropriate package to meet your needs.
For me anyways, it was nice having the dining plan, because the food is pretty expensive at Disney. Even if it didn't save me any money, I would have anxiety over paying $60-$100 for every meal and the dining plan was well worth it.
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