Hi Jessica!
Thanks so much for asking your question here on the Moms Panel. Star Wars Weekends is my family's favorite special event, so I had to pop into light speed to answer this for you!
For your 5 year old little padawan, I suggest signing him up for Jedi Training Academy. It's one of the best experiences that Guests of Yoda's stature can have, and he'll be so excited to defeat Darth Vader. If you'd like to have him experience this, you'll want to arrive at Disney's Hollywood Studios no later than 7:30 a.m. Sign-ups start about half an hour before park opening, and Hollywood Studios opens at 8:00 a.m. on the day that you plan to visit.
Be sure to ride Toy Story Mania with your little one. I think it's the second best family-friendly attraction at Hollywood Studios, with Star Tours being the first!
While there's plenty of pixie dust at Hollywood Studios, a visit to Magic Kingdom Park to parlay with The Pirates League would be so fun for your son.
The Pirates League is always a favorite for boys and girls alike. He'll be transformed into his choice of pirate look, get a special pirate name, and say the Pirate Pledge. It'll be a memory he'll talk about for years to come!
I hope this answers helps you with your vacation planning, Jessica. If you have any other questions, feel free to ask us anytime. We're always here for you.
Have a magical vacation and may The Force be with you!