Everyone is different. Personally, I like doing something special on my actual birthday but I know a lot of people celebrate before, on actual date, and after their birthdays. If you plan a special dinner while at Disney, I would still do something on a smaller scale at home on his actual bday. However, being at Disney around this milestone birthday, would be fun to plan a special dinner or have something like balloons, candy, wine, etc. in the room for a quieter celebration. Some of the cakes look so good. Also, there are some great restaurants to choose from. Shulas at the Dolphin Resort is wonderful. Expensive and not on the dining plan, but it has been top rate the two times we had dinner there. If you do decide to go all out while at Disney, take a lot of pictures and enjoy looking at them on his actual day.