Hi Russell! How lucky that you have two upcoming visits to Walt Disney World! Upgrading to an Annual Pass can often be a real money-saver when you have two trips planned in a year, so you're smart to be thinking about this option.
Whether you can upgrade your 5-Day Park Hoppers to an Annual Pass will depend on the type of discounted ticket you have, and ultimately you'll need to speak with one of the ticket agents in person at a Walt Disney World Guest Services location for an official answer to your question. In general, guests who purchase discounted tickets, such as those from Disney packages or authorized ticket re-sellers, are often able to receive full credit for the gate price of those tickets when upgrading to an Annual Pass after using at least one day on those tickets. However, special tickets, such as those purchased through the
Disney Youth Education Series program, generally cannot be upgraded to Annual Passes. If your school package Park Hoppers may be used only during a certain time frame, they are likely the type of tickets that cannot be upgraded. I recommend that you visit the ticket window at one of the parks during your school trip to discuss the potential upgrade options for your particular tickets.
Wishing you a magical vacation! Come visit us again at the Moms Panel if you have more questions! We're always happy to help!