My husband and I were the same way. The only vacations we had ever done were Caribbean cruises, in state trip, or to Ohio to see my family. I had been to Disney before and I truly believed he would enjoy it. I just explained to him how much I wanted to go and how much I wanted to experience the magic with him. He reluctantly agreed to go. I booked the trip for Christmas because he LOVES Christmas time and I figured I would take any extra help I could get lol. He ended up LOVING Disney and insisting we try to go back every year. That was in 2010, and we've since gone back last year, and are planning our Christmas trip for 2012...and now he's even seeing if we can swing a Spring trip!.