Cruise ship anchored near a tropical beach with turquoise water and small sailboats in the foreground.
  • On Jun 28, 2026
    Katherine from FL Asked Please note that experiences, policies, pricing and other offerings are subject to change and may have changed since the date of this answer.

    Hi! We will be cruising to Castaway Cay soon. My husband is an experienced sailor, and our teen son is on the High School Sailing Team. What documentation of skill do we need to submit to rent a sailboat at Castaway Cay? How many can ride in the boat?

    Ahoy there, Katherine!

    Welcome to planDisney, and thank you for sending in your question. It sounds like your crew is full of skilled seafaring sailors! I'm sure all of you are excited to board your Disney Cruise ship since you feel right at home on the open seas. My family always enjoys watching the ship dock (if we are up early enough) and preparing to sail away from each port. On Disney Castaway Cay, we like to go to Deck 4 port side to see the ropes drop and wave goodbye to the Cast Members who have a magical way of saying "See ya real soon!" 

    Katherine, when you visit Castaway Cay, you'll be able to sail on a Hobie Cat around the beautiful Boating Harbor, with unique views of your Disney Cruise ship. I recommend having a waterproof camera (make sure all loose items are secured) or your phone in a waterproof pouch to snap spectacular photos with the ship as the backdrop. No official documentation is required, but the staff will review your husband's sailing experience with some questions and a short skills assessment to make sure he is qualified to maneuver the boat. He'll need to steer the way on this particular excursion, as the Disney Cruise Line requirement is 18 and up. Four sailors (ages 5 and up) can enjoy this Port Adventure together on one Hobie Cat. My fingers are crossed that the weather will cooperate so your crew can head to Boat Beach to grab your lifejackets and head out on your journey around the harbor. I know it will be an exciting adventure and a memorable day on Castaway Cay.

    Thank you for allowing planDisney to help with your upcoming Disney Cruise Line vacation, Katherine. With July underway, it won't be long now. Keep us posted with any other last-minute questions you have before your cruise with Mickey!

    Have a magical day,
    Nancy
thumbnail image for Nancy

Meet the Panelist: Nancy, Georgia

Ahoy there! I am excited to help you with your pixie-dusted voyage on board Disney Cruise Line! I have been fortunate enough to have sailed for the last two decades with Captains Mickey and Minnie, and I look forward to helping you plan your magical journey.  Learn More About Nancy

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