The most reliable way to tell if your specific sailing has a "Pirate Night" is to check the Disney Cruise Line Navigator App once your booking window for activities opens. A common "pro-tip" used by veteran cruisers is to look at the Bibbidi Bobbidi Boutique (or "Pirates League") reservations; if you see a "Pirate Makeover" package available for a specific day, that is almost certainly when the party will happen. Pirate Night is standard on most Caribbean and Bahamian itineraries but may not occur on shorter 2-night cruises or certain European/Alaskan sailings. Once you are on the ship, the app will show the full schedule, including the "Mickey's Pirates in the Caribbean" deck party and the famous fireworks at sea. You will also likely find a pirate-themed bandana in your stateroom on the morning of the event. To be fully prepared, it's always worth checking Disney Cruise forums or fan sites for your specific ship and route, as the themed nights are relatively consistent across similar itineraries.