Orlando Florida as a kid due to Disney World & Universal Studios Theme Parks.
Tampa Florida, city along the water in Florida, what's not to be excited about?!
D.C as an adult, OK city.
Boston as an adult, due to my hobby, NOT the people.
I would say Philly but all my trips there have been day trips from NYC, never stayed the night over so I never got to truly enjoy the city. I usually visit Philly to ride Septa for hobby reasons, never ate an cheesesteak there ethier.
I always wanted to run up the Rocky steps in Philly, but never did.