Hi there, Christine!
Welcome to the Disney Parks Moms Panel! I am so glad to hEAR that you will be heading out on your first Disney Cruise Line vacation. Even with a short two-night sailing, you will still get to experience the fun and excitement that goes along with every Disney Cruise Line vacation!
Your sailing will include both Pirate Night and
Halloween On The High Seas festivities! Currently,
Pirate Night is scheduled for your first night onboard, but the schedule of onboard Halloween activities will not be available until you board the ship. My family's favorite event is the Mickey's Mouse-querade Party where you can trick-or-treat in the atrium with your favorite characters! Costumes are completely optional, and you can still participate in the fun even if you choose not to dress up! My family recently went on a three-night sailing and we opted to not take Halloween costumes, but rather my boys just dressed in their pirate clothes for both Pirate Night and the Halloween events. This cut down on luggage and they didn’t mind one bit!
You will see other Guests in costume, as pirates, in cruise casual wear – quite the variety and my recommendation is to go with what makes sense for you and what is comfortable! You likely won’t be in a Halloween costume for an extended period of time, so if leaving that behind and saving it for the actual holiday works best, go for it! Or, if you have a unique and fun costume that you want to wear multiple times this season, bring it!
Wishing you the most magical and WONDERful adventure at sea!
Happy Sailing!
Stephanie