Family fun on board; grandparents; Pirate Night; Main Deck
  • On Aug 21, 2025
    Karen from UT Asked Please note that experiences, policies, pricing and other offerings are subject to change and may have changed since the date of this answer.

    Sailing on Disney Fantasy 5 night Bahamian cruise….(port Canaveral, Nassau, Lookout Cay, Sea, Castaway Cay, Port Canaveral) which day is pirate night? I have tried looking it up but the different ordered itinerary has me confused… can you help?

    Ahoy there, Karen! Thanks for sailing by planDisney.

    You have a fantastic cruise coming up! One of my favorite itineraries is a double-stop at Disney's private islands. You get two full beach days, each with its own vibe. Castaway Cay is the OG with bike rentals and all the active water fun, while Lookout Cay shines with its food choices and gorgeous, gorgeous beaches. Combine that with a pirate night at sea full of swag and pyro, and you have the most fantastic cruise!

    It looks like your cruise is a Halloween on the High Seas sailing, so you can anticipate a Halloween night and a pirate night. While the schedule is subject to change, this is what you can expect on your five-night itinerary:

    • Night 1 (All aboard!): Cruise casual - feel free to wear anything, but swimsuits and tank tops aren't allowed in the rotational dining restaurants.

    • Night 2 (Nassau): Halloween night or cruise casual - tonight is the night to go ALL OUT! Adults and kiddos can dress up like their favorite characters and enjoy the fiendishly fun activities across the ship.

    • Night 3 (Lookout Cay): Formal night - jackets for men and dresses or pantsuits for women. Don't be surprised when you see your fellow sailors vogueing like Edna Mode in tuxes and gowns. They are taking advantage of the fantastic onboard photographers for formal family pictures, and I suggest you do the same!

    • Night 4 (At sea): Pirate night - grab your scalliwag swag and party like a pirate!

    • Night 5 (Castaway Cay): Cruise casual - the perfect night to chill after a sun-drenched sail.

    Once onboard, the Navigator app will allow you to keep up to date with all the magical happenings. If you have any other questions, feel free to float back to us. I wish you a magical sailing!

    Rayna
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Meet the Panelist: Rayna, Florida

Hi y'all! I'm Rayna: wife, mom, anesthesiologist, and long-time Disney enthusiast. I've lived all over the country, but these days life has my family of seven in Florida. We're fantastically close to the most magical place on earth, and as Annual Passholders and Disney Vacation Club members we couldn't be happier about it. We've visited almost every Disney Vacation Club resort, so I'm thrilled to be here doing what I do best: Helping plan magical vacations. Learn More About Rayna

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