Family at Lookout Cay
  • Jan 26, 2026
    Please note that experiences, policies, pricing and other offerings are subject to change and may have changed since the date of this answer.

    I'm trying to figure out how to plan a cruise I had gone twice when I was younger. really enjoyed it. now I would like my grandkids to experince what I did

    Ahoy, friend!

    Thanks for sailing by with your question. I'm thrilled you are considering a multi-generational voyage and am happy to serve as your first mate in the early planning stages of your process.

    The easiest way to begin planning is by navigating to the Disney Cruise Line website. On the main screen, you'll see the option to "Explore Destinations" just below the page header. You can use each drop-down box to narrow down when you'd like to sail, your target destination, where you'd like to depart from, and the number of guests in your stateroom (note: each stateroom will need to be booked individually, but you can link multiple reservations together for dining/planning). You can also click the "More Filters" option to narrow down your sailing length, preferred ship, and whether you'd like to experience a themed or holiday cruise. Once you've input your preferences, click "View Dates" to see a full list of your options.

    I went through this process myself just last week while searching for an itinerary that visited both Disney Castaway Cay and Disney Lookout Cay at Lighthouse Point in early 2027. I highly recommend visiting one of these gorgeous Disney Island Destinations if you can, as both are packed with family fun, Character encounters, entertainment, activities, and plenty of Disney magic. My family has enjoyed Castaway Cay on many occasions, but just experienced our first visit to Lookout Cay in December, and we absolutely loved the powder-soft sand, tropical foliage, and delicious food! We're so excited to return next year, and are already keeping tabs on the countdown in our Disney Cruise Line Navigator app.

    Once I found the perfect sailing, I was able to select my stateroom and pay the deposit online in a few simple steps, but you can complete the process with a Disney Cruise Line Crew Member by phone if you'd prefer to book your cruise with a little extra assistance. They'll be able to answer questions specific to your sailing and can assist with booking multiple staterooms, if necessary.

    At this time, bookings are available from February 2026 through May 2027. We should expect to see the 2027 Summer and Fall itineraries soon, as they are typically released 13-18 months in advance. While researching the perfect itinerary for your family, spend some time reviewing our planDisney Pocket Guides to get a better feel for the fleet's ships and peruse this Disney Parks Blog article about Disney Destiny, which made its maiden voyage in late 2025. I already have my sights set on Disney Treasure or Disney Destiny once we complete our upcoming sailing.

    I hope this helps get you started on a most magical adventure! If you need more specific guidance or recommendations, please don't hesitate to come back to planDisney and let us know. We're always happy to help!

    Bon Voyage,
    Amy
thumbnail image for Amy

Meet the Panelist: Amy, North Carolina

Hi, I'm Amy- a proud wife, mom, and Disney adult. I'm a natural planner with a flair for the creative, always looking for ways to add a little magical sparkle to our family's day-to-day happenings and once-in-a lifetime moments. You'll find me and my crew visiting the parks from rope drop to close and packing in as much magic as possible to each day of our Walt Disney World Resort vacation. From dining to photo spots and all the details in between, you've got a friend in me! Learn More About Amy

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