Day 4: Castaway Cay—Leo’s Birthday Bash & A Full-On Cornell Takeover

Leo woke up officially a teenager, and what better place to celebrate than Disney’s private island? We were commenting on how fun it is that we often get to see Leo on his birthday–Moab, Steamboat, Copper Mountain, etc. He said, “Yeah…and that has nothing to do with the fact that your Spring Break usually lines up with my birthday.” I assured him that wasn’t the case–we just love him the most. Lol. We kicked things off by sleeping in and enjoying a leisurely breakfast, which included the most magical creation of all time—churro waffles. The weather? Absolutely perfect.

Once we made it off the ship, we grabbed a group family pic with Jack Sparrow, because obviously, we couldn’t pass that up. Then, we claimed a shady corner of the beach, dragging a ridiculous number of chairs together to set up shop for the day.

Gwen and Blake had some deep beachside conversations, while Mave convinced me to go down the waterslide with her—an experience that cost me my sunglasses. Later in the day the adults set off on a bike ride to the lookout tower, soaking in the stunning ocean views.

Ice Cream, Splash Balls, and Beach Shenanigans

Blake took on the very important job of guiding everyone to the self-serve ice cream machines. And by guiding, we mean treating himself to ice cream on every single trip. He clocked in at six or seven cones, while everyone else averaged at least three.

Josh and Blake’s fish extender gift of splash balls turned out to be the MVPs of the day. Those little things provided nonstop entertainment, from beach battles to surprise attacks. Rusty said his favorite moment of the trip was right at the end of the day when most everyone else had already gone back to the ship and it was just our family playing in the water and along the sand with the Wish gleaming in the background.

Over in the water, Gwen became the human motor for Nat and Carlie, powering them across the ocean on their raft. We attempted snorkeling, but the underwater sights were a little underwhelming—though a few lucky people did spot a stingray!

Lunch at Cookies Too hit the spot before Halle and Josh snuck off to the adults-only beach, where they enjoyed drinks and lounged in hammocks like the responsible young adults they now are.

Dan, the self-proclaimed cruise hater, gave the best compliment while we were relaxing on the beach. He said he would totally do a Disney Cruise again. I’m just so glad everyone loved it. It’s not easy to take time off work and wrangle kids who are underslept and over sugared.

Birthday Drinks & One Overwhelmed Bartender

The plan was to celebrate Leo’s birthday with drinks from Olaf’s Summertime Freeze on the island, but in true vacation fashion, we completely missed closing time. No problem—we pivoted and decided to grab the Drink of the Day back on the ship instead.

What we didn’t consider? Ordering 13 drinks at once might stress out the bartender a little. Oops. But hey, we got our celebratory drinks, and Leo’s birthday was properly toasted!

Aladdin, 1923, and One Last Karaoke Takeover

That night’s show was Aladdin, and while we had box seats in the balcony, our view was slightly restricted. Not a huge deal, because Jafar and Iago literally stood right next to us for part of the show! Fun moment, but as a family, we unanimously agreed that The Little Mermaid was still the superior production.

Dinner at 1923 was the perfect final meal. The burrata appetizer was to die for, and Blake—forever the food critic—claimed the filet mignon was “crockpot.” He’s ridiculous. It was delicious.

One last karaoke party

Grandma really wanted to hear the kids sing, so we went all in. Gwen, Halle and Mave crushed Mamma Mia, and Jhena made the host cry with her gorgeous rendition of Part of Your World. He was so impressed with Halle’s performance from Waitress that he told her she should be on Broadway.

Then came the party set.

• Leo, Simon, and Jack got the whole crowd rocking with Life is a Highway.

• Rusty shook his little booty while he and Blake brought down the house with Livin’ on a Prayer.

At that point, it wasn’t just karaoke anymore—it was the Cornell Family Concert. Nat and I really wanted to do Battle of Yorktown from Hamilton, but they didn’t have it. Cry.

We thought that would end our evening. But no–a little bit later the kids came bursting into the room, saying that Blake had locked himself in the bathroom. We went to check, and sure enough, the latch was broken and he was stuck in that teeny tiny bathroom. We tried to get him out, but after several failed attempts we had to get maintenance to get the job done. Good thing we took up most of the hallway, because the midnight laughter and screaming surely kept anyone awake who was unlucky enough to be in our general vicinity.

By the time we left in the morning, we were all that specific kind of exhausted that makes you feel slightly delirious and very in need of a vegetable. But even with all the chaos, we wouldn’t trade it for anything.

Because here’s the thing: family vacations aren’t about being rested. They’re about stories like these—late-night lock-ins, midnight karaoke, and playing together on the beach. It’s what makes the memories stick. And the fact that we got to do it all with people we love? That’s the real magic.

Mom and Dad–Happy 70th birthday. Thanks to you, we have family who are our friends. And we wouldn’t have it any other way.