Yes, you can upgrade your Walt Disney World Annual Pass from the Pixie Dust Pass to the Pirate Pass, but there are specific 2026 rules to follow. You can typically only upgrade your pass during your renewal window, which begins 60 days before your current pass expires and ends 30 days after. During this time, you simply pay the difference in price between the two tiers. However, if you are outside your renewal window, Disney occasionally allows "mid-year" upgrades, provided the higher-tier pass (the Pirate Pass) is currently available for new sales. If the Pirate Pass is "sold out" or restricted to renewals only, you will have to wait until your expiration date to make the switch. Remember that the Pirate Pass offers fewer "blockout dates" than the Pixie Dust Pass, including access on most weekdays and many weekends, making it a popular choice for locals who want more flexibility without the cost of the Sorcerer or Incredible pass tiers.