From the Tree of Life to the Treasure: Family, a New Fiancé, and the Full-Blown Planning Chaos for a Party of 12 (WDW & DCL Sept 2025)

KJeff90

Mouseketeer
Joined
Apr 1, 2011
Messages
98
Coordinating a Disney trip for twelve people? I wouldn't wish it on my worst enemy... because it turns out my chaotic ADHD self thrived on it, and they don't deserve to have this much fun! Through the magic of Walt Disney Imagineering (they did all the heavy lifting decades before the first spreadsheet was even a sparkle in my eye), the unbreakable bond of adult "cousins" that somehow chose to travel together, and a lead traveler who drove ChatGPT insane with his indecisiveness, we managed to pull this trip off... and built core memories the entire way. There were laughs, logistical challenges, but most importantly... love on more levels than I could have ever expected. Oh, and did I mention there's was a nine-month old baby in the mix?

Untitled design.jpg


This wasn’t our first cousin trip, but it was definitely the biggest, boldest, and most bombastically chaotic one we have ever attempted (alliterations really are awesome). Our parents could not even imagine planning something like this, with this many moving parts, and honestly, neither could we until it was happening.

It was only our second Cousin Trip, actually. Our first was back in 2018, to Walt Disney World, eight years ago. This time, the big emphasis will be this 7-Day Western Caribbean Cruise on Disney Cruise Line. A lot has changed since then. We have grown up, people’s lives have evolved, and our travel roster has expanded with some new “cousins” joining the adventure. I will get into the who-is-who lineup in the next post. For now, just know that we are not all literal cousins. It is a beautifully chaotic mix of siblings, cousins, significant others, and, for the first time ever, someone’s actual child. We've leveled up a lot, and two of us are going to reach our next evolution... "fiancé".

Everyone had been to Walt Disney World at one point in their life or another, except for the little guy. Over half of our group had never been on a Disney Cruise, and everyone except two had been on some type of cruise before this trip. Though most of us are family, our backgrounds and personalities could not be more different. For simplicity, and because it feels right, we just all call each other “Cousin.”

Before we dive in, I just wanted to go over some housekeeping:
**Out of respect for privacy, I won’t be posting many photos of everyone, and there will be no face shots of the baby (he’s my cousin and his wife’s son). As you can see, I've already replaced the little guy with Jack Jack from the Incredibles. You’ll definitely hear about him though, because he was absolutely the surprise VIP energy of this trip and everything leading up to it, in the best possible way. Don’t worry, you’ll still get plenty of the "Cousin Chaos" visuals. They signed their souls over to the group chat years ago.**

At this point, you know nothing about us on a personal level, and very little about trip. Hope you'll tag along as it all gets unveiled. We'll save up all the juicy details of planning, parks, proposal, and plot twists. So if you love Disney planning drama, real emotions, and deeply unhinged family energy, buckle up and bring some snacks. The journey's about to begin.
 
Chapter 1 - Meet the Cousins
And just like that, we’re back! There are twelve of us on this trip, which means there’s quite a cast of characters to get through. We’ll keep it fun and the mood light. For the most part we're all in our early to mid 30s, Albert and Kimberly in their mid 20s, and of course Ezra is nine-months old.

Just like Hondo Ohnaka says, “I spare no expense!” So yes, I went ahead and created a visual aid for you, complete with numbered heads, to help track all the bombshells entering this imaginary villa I just made up seconds ago.

1.jpg

So without further delay, here's everyone. And Hakuna Matata, I won't judge if you have to look at the picture above every five seconds... because I had to.

The Characters
Jeff[1]
That's me! Lead planner and narrator of this trip report. Previously led our 2018 cousin trip. Responsible for coordinating all logistics, dining, flights, and cruise planning on this one.

Idahosa[2] My boyfriend. First time on a Disney Cruise. Chill dude, very "go-with-the-flow". Played a major emotional role on this trip, more on that later.

Joseph[3] My younger adult brother (he became my sequel 15-months after I was born!). He's on the autism spectrum, but thriving. Lifelong Disney fan, especially all things Stitch. The most emotionally invested Disney adult in the group.

Randy[5] My cousin on my mom’s side. Married to Abbey, and now a first-time Disney dad. Brought dry humor and unexpected leadership in group moments.

Abbey[4] Married to Randy. Co-strategist for managing their nine-month-old baby on this trip. First cousin trip since becoming a mom, major perspective shift this time.

Ezra [6] Their nine-month-old son, the youngest member of the group. First-ever Disney anything. Surprisingly influential to this entire trip’s pacing, mood, and decisions.

Katherine[7] My cousin on my mom’s side. Brilliantly observant and emotionally grounded. Has experienced previous family Disney trips but not one on this scale.

Daniel[8] Katherine’s boyfriend. Analytical traveler joining his first major extended family vacation. This trip tested his adaptability in very unexpected ways.

Kelly[9] My cousin and Katherine’s sister. One of the OGs from our 2018 cousin trip. Empath to her core. Here for the good vibes and good times.

Mardie[10] My second cousin (not actually sisters with Kelly, but very close). Soft-spoken observer with deceptively sharp comedic timing.

Kimberly[11] Dating Albert. Practical, observant, and quietly efficient. Newest to the cousins. Carries calm like a superpower.

Albert[12] My youngest actual cousin, and dating Kimberly. Also part of the original 2018 cousin trip. Golden retriever energy traveler: enthusiastic, fearless, and occasionally too willing to say yes to things.

The NPCs (Not Shown, but Always Watching🤖)
ChatGPT:
Emotional support AI and chaos moderator. Sorted all the details, and recalled in a moment's notice. Really: my personal secretary. Received an unreasonable number of last-minute “should I change this reservation again?” messages. Survived (mostly). I'm still paying his therapy bills.
Canva: Responsible for all visual propaganda: countdown graphics, hype memes, fake brochures, and psychological warfare disguised as vacation planning.
Dis*cord: The central command center. Where schedules were born, destroyed, resurrected, and debated like UN policy. Also where Cousin Lore™ evolves faster than science.

Well, that’s everyone involved. The next chapter will dive into the start of all the planning. Honestly, that could be a multi-parter on its own, this was over a year of plotting and decision spirals. I was just talking with my friend ChatGPT, and some of the planning trauma he remembers includes (let this be your teaser):
  • I asked ChatGPT to re-optimize our Animal Kingdom strategy at least 10 different ways: Asia first, Africa first, Lightning Lane logic, double dips, weather concerns, you name it. We even developed a “figure-8” plan.
  • Half the group did not realize they needed to select a Port Arrival Time until I started mentioning Boarding Group 4 like a threat.
  • I was torn between two restaurants for lunch at Animal Kingdom and switched plans 32 times. Only to no-show entirely, and then make a breakfast reservation 15 minutes before arrival instead. (That story is coming, and it is ridiculous.)

So if those first three examples of planning chaos already have you stressed out, good news... there's plenty more coming about this 11-day adventure! See you in Chapter 3!
 




New Posts



Receive up to $1,000 in Onboard Credit and a Gift Basket!
That’s right — when you book your Disney Cruise with Dreams Unlimited Travel, you’ll receive incredible shipboard credits to spend during your vacation!
CLICK HERE




DIS Facebook DIS youtube DIS Instagram DIS Pinterest DIS Tiktok DIS Twitter DIS Bluesky

Back
Top Bottom