Mom and child as pirates on Castaway Cay; ship in far background
  • On Nov 1, 2025
    Kelsey from WI Asked Please note that experiences, policies, pricing and other offerings are subject to change and may have changed since the date of this answer.

    We're going on our first cruise in January, 5 nights on the Fantasy leaving 1/23/26. We're big foodies and want one special date night at Remy but don't want to miss pirate night or a show with our kids. How will we know when those are?

    Ahoy there, Kelsey, and welcome to planDisney! Your first cruise is just around the riverbend, and I’m all a flutter that I get to be the one to help you with your plans.

    It looks like you’ve already charted a course with amazing adventures and culinary delights in mind. To start off, make plans to be up on deck after dinner on Night 2 for the Pixar Pals Celebration and The Incredibles Deck Party. Your dress attire for that evening is either Cruise Casual or Pixar-themed; just be sure to follow Disney’s costume guidelines if you do decide to dress up.

    Then, on Night 3 after your day at Lookout Cay, prepare to pull out something sparkly from your suitcase for an Optional Dress-Up Night. After docking at Castaway Cay the next morning, you’ll have plenty of time to play in the sand and sea at one of my favorite Disney destinations. I recommend purchasing the Castaway Cay Getaway Package so you have a float, bike, and snorkel at the ready to explore the island all day long.

    Once you embark again, look out for a red bandana for each member of your family in your stateroom before dinner, and then get ready to feast on a Caribbean-themed dinner in the rotational dining rooms for Pirate Night! You’ll want to join your fellow scalawags up on the pool deck after dinner for your Pirate Night Deck Party, including fireworks at sea (assuming the weather cooperates and Jack Sparrow doesn’t throw a spanner in the works).

    Your first and final nights are considered “Cruise Casual”, so how you decide to dress is completely up to you. As far as when to book an adult-exclusive dining experience like Remy, I would refer to your Disney Cruise Line Navigator app. Once you step onboard and connect to the free DCL-GUEST WiFi, you’ll have the most up-to-date schedule in the palm of your hand, highlighting everything from theme nights to showtimes. If you decide to reserve a dinner experience in advance and want to make changes once on board, the dining team will be happy to assist you.

    Finally, as a first-timer, I have a few must-haves I wanted to suggest as you prepare your packing list. I always bring towel clips (to both secure the provided towels to my lounge chair and distinguish them from the others), insulated reusable mugs for the complimentary beverage stations around the pool, and magnetic decorations for our stateroom door. When it comes to necessities like travel documents and medications, make sure to pack those in a carry-on bag so you have them with you on embarkation day.

    I could go on and on about everything I love to see, do, and eat on a Disney Cruise, but the magic also comes from letting you discover some of these surprises for yourself. That being said, if you think of anything else I can help you with before you set sail, don’t hesitate to write me back here at planDisney!

    SEA ya real soon!
    Sami
thumbnail image for Sami

Meet the Panelist: Sami, Tennessee

Hey Howdy Hey! I'm Sami - an author, TV Host, & new empty-nester living in Nashville with two teenagers in college. We enjoy sports, live music, and making magical memories aboard Disney Cruise Line & in Disney Parks worldwide. I raised my kids just around the riverbend from the Walt Disney World Resort and celebrated every milestone with their Disney friends. With so many incredible itineraries and delicious dishes on board, I love helping my extended ohana discover a whole new world at sea! Learn More About Sami

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