Lookout Cay
  • On Oct 24, 2025
    Cooper from LA Asked Please note that experiences, policies, pricing and other offerings are subject to change and may have changed since the date of this answer.

    Looking for a good time t cruise for a family of 5 anytime of the year

    Ahoy there, Cooper!

    Welcome aboard planDisney! With a crew of five ready to set sail, it sounds like you’re about to make some unforgettable memories filled with sunshine, sea breezes, and a little Disney magic around every corner!

    Now, I’ll admit—I’m probably as biased as Captain Jack Sparrow’s compass when it comes to picking a “best” time to cruise, because truth be told, any time I’m on a Disney ship feels like the best time of year. But the real treasure lies in what kind of adventure your crew is after. If your family loves larger-than-life heroes or animated adventures, sailings with Marvel Day at Sea or Pixar Day at Sea (usually from January through March) might be perfect. Prefer to trade your capes for coats? An Alaskan itinerary between May and September offers breathtaking views, wildlife, and enough wonder to make even Elsa say, “The cold never bothered me anyway.”

    If theme isn’t a deciding factor, maybe the ship itself will be your guiding star. Each one has its own personality—kind of like the characters we all love. The Disney Magic holds a special place in my heart. Its cozy size, the thrilling AquaDunk, and Rapunzel’s Royal Table make it my personal favorite (and it’s especially great when visiting Castaway Cay or Lookout Cay since it tends to feel less crowded). Meanwhile, the newer ships like the Wish, Treasure, and the upcoming Destiny offer dazzling modern touches, with the Hero Zone serving as the perfect playground for family fun—from basketball and ping pong to air hockey showdowns that could rival a Lightning McQueen photo finish!

    If your heart is set on exploring specific destinations, I recommend starting with the itinerary. Personally, I can’t resist any sailing that stops at both Castaway Cay and Lookout Cay—it’s like a double helping of pixie dust! Once you’ve narrowed down your dream route, pick the ship that feels right for your crew’s style and priorities.

    You might also consider timing based on your budget. I’ve found that months like January, February, August, and September often offer better value since many families are in school-mode rather than cruise-mode. Just steer clear of major holidays when fares tend to rise faster than Aladdin’s magic carpet!

    Once you’ve found your perfect match, you can book online through the Disney Cruise Line website or call one of the wonderful Cast Members who can help you plan every nautical detail.

    I hope this helps you chart a course toward smooth sailing and magical memories. Whether your crew is craving tropical sunshine, cool Alaskan air, or a themed voyage that brings your favorite Disney stories to life, there’s a Disney Cruise Line itinerary waiting to make your hearts sing like Sebastian’s band.

    Sea ya real soon with boo-tiful nights and frightfully fun days,
    Dustin
thumbnail image for Dustin

Meet the Panelist: Dustin, Florida

Ahoy, me hearties! I’m Dustin—a husband, father of two, and active-duty service member living in sunny Florida. My crew and I “just keep swimming” toward our next Disney Cruise Line adventure! From “a whole new world” of ports to “hakuna matata” vibes on deck, we live for the magic at sea. Ready to see what’s “beyond the reef”? Allow me to be your guide as we sail toward your perfect Disney Cruise adventure! Learn More About Dustin

Related Video

  • thumbnail image for Disney Cruise Line First Timer Tips | planDisney Podcast – Season 2 Episode 1

Didn't find what you were looking for? Click the Ask a Question button to open the Ask a Question dialogue box. If you are not logged in a dialogue box will appear to signin in order to ask a question.

To submit your question, please log in now if you have not already done so.

Ask a QuestionOpens the Ask a Question dialog box.
x

Update Browser

For a better experience browsing this website, please download an updated version of Internet Explorer.


Or you can continue browsing without updating.