Hi Christy!
I bet your family is getting excited just thinking about the possibility of a Walt Disney World Resort vacation next year! My youngest son also loves Jake and the Never Land Pirates and loves getting the opportunity to see Jake in person at the parks.
There are a couple of things at Disney's Hollywood Studios that I think your son would love. You can enjoy a special character dining experience with Jake at Disney Junior Play 'n Dine at
Hollywood & Vine. The Disney Junior characters make appearances during breakfast and lunch, and your son will be able to get autographs, pictures and even dance with Jake! Advance reservations are recommended and can be made up to 180 days prior to your visit. I would also suggest checking the website closer to your trip since character appearances are subject to change.
Disney Junior - Live on Stage is also a great opportunity for your son to see Jake. This fun-filled puppet show invites preschoolers to get up and sing, dance and play with their favorite characters from Disney Junior. There are usually several shows throughout the day so be sure to check the Times Guide for exact show times when you arrive at Disney's Hollywood Studios.
The second week in January is typically less crowded as most children are returning to school. There are certain
runDisney events that are held each year that typically will draw large crowds. You can check the website for specific dates, but I feel sure that would be a great time to visit!
Please let us know if you have any other questions, and I hope your trip is everything you dreamed!
~Carrie