In November 2001, Stephen, along with his best friend from college, Annie Laurie Crane, took their second trip of the year to Walt Disney World. While working in Washington D.C., Annie Laurie befriended Jon Vaden, whom she lovingly nick-named Jon Disney, after his well-known affection for the Disney properties. Jon traveled with Annie Laurie to Orlando and met up with Stephen for the trip. Jon stayed at his friend's Mike, who also hung out with the crew while they were there.
The trip was a first time for several things for the crew. Annie Laurie and Stephen stayed at the Walt Disney World All Star Movies resort, the first time either had stayed on-site. In addition, they took a behind the scenes tour of the Magic Kingdom, the first time either had been in the tunnels, or Utilidors, beneath the park. Although not a first for Annie Laurie or Jon, they group was able to ride in the pilot's cab of Monorail Yellow, the first time Stephen and Mike had been in the front of a monorail.
This journey to Walt Disney World would not be the last for Stephen and Annie Laurie. Through the years, they continue to visit the parks, taking part in such events as the Food and Wine Festival and the 100 Years of Magic Celebration. However, this trip was special because of the new friends that were made and the addition of Mike "Space Monkey" Sendek and the Jon "The Jonorail" Vaden-Disney.