I generally leave my pistol at home when on a vacation like yours. However...
As I understand it, Disney supposedly has lockers available to secure your pistol. You might confirm this before you decide. I haven't been to Disney in years; my only daughter is 15.
When I am on a vacation like you describe, I tend to consume more alcohol than normal. If I can't carry the gun at the parks, and can't carry at night due to drinking...well, I may as well leave it at home! Ditto when I go to California wine country.
If I am visiting family in CT, they have pistols to loan me and I have a non-resident CT CCW.
If I am driving to my destination, I almost always bring a firearm, assuming it's legal. Flying with guns is no big deal at all in Arizona, since guns are even more common than illegal aliens there...but of course I can't speak for Kansas.