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) Updated 11/1!!

[KJeff90]

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?



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.

 

[KJeff90]

The Table of Contents
You can click these chapters below for wayfinding, or getting lost. Choose your own adventure pals!
Pre-Trip/The Planning Chaos
One little spark, of inspiration.
Is at the heart, of this vacation...
Chapter 1 - "Meet the Cousins"
Chapter 2 - "Planning Began a Long Time Ago, In a Galaxy Far, Far Away From Florida: California"
Chapter 3 - "Live. Laugh. Logistics." (Part 1)
Chapter 4 - "Live. Laugh. Logistics." (Part 2)
Chapter 5 - "Keeping Interest with Memes"

Travel
When you start off "Soarin' Over California" ...then leave it to float away from the Florida Coast.
~Coming Soon~

Pre-Cruise Adventures
Where plans meet reality, and reality responds with a big ol' "nope".
~Coming Soon~

Adventures Aboard the Treasure and Exploring the Western Caribbean
Seven nights. Twelve People, Five Staterooms. One Large Balcony. Zero Chill.
~Coming Soon!~

Post-Cruise Adventures
Re-entering society with unlimited data, limited motivation, and one too many souvenirs.
~Coming Soon!~

Real Life Adventures and Beyond
We Came. We Saw. We Continue to Wonder When Our Next Cousin Trip Is?
~Coming Soon?~

Next Chapter Being Worked On, and Coming Soon:
Chapter 6 - "#super-secret-side-quest"
Chapter 7 - "The Great Upgrade Cascade" (Really, Just Part 3 of "Live. Laugh. Logistics."

 

[KJeff90]

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.



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 2!

 

[alohamom]

I love this.
I also have an extraordinary large extended family of "cousins" (some real, some honorary) and I get this vibe so I'm enthusiastically following!

psychological warfare disguised as vacation planning.

OMG-printing this out and putting on my office wall LOL

Cousin Lore™

 

[princesserin1350]

So excited for your report! My husband and I got married on a Disney cruise last year with a bunch of our family and friends sailing with us, so I'm excited to see how another large group manages a Disney cruise together.

 

[liamthompson]

I remember your pre-trip question about proposing to your boyfriend at animal kingdom and then where to eat afterwards with the cousins!!! Excited to see that you have "leveled up" to fiance, congratulations!

 

[KJeff90]

I also have an extraordinary large extended family of "cousins" (some real, some honorary) and I get this vibe so I'm enthusiastically following!

It really was something. From the spark of "we're due for a cousin trip", to the after trip "dang, we really just did all that". It was really a group effort. I'm, hoping to share the trials and tribulations of it all. Maybe even teaching moments, lol.

So excited for your report! My husband and I got married on a Disney cruise last year with a bunch of our family and friends sailing with us, so I'm excited to see how another large group manages a Disney cruise together.

The thought of traveling with a dozen people seemed intimidating, but wait until you see all the logistical hiccups and improvising that had to happen!

I remember your pre-trip question about proposing to your boyfriend at animal kingdom and then where to eat afterwards with the cousins!!! Excited to see that you have "leveled up" to fiance, congratulations!

The afterwards worked out to plan, everything before 6:00pm did not.... but in the best way. It'll be a few posts away, but we'll get to how that day unfolded!

 

[KJeff90]

Chapter 2 - "Planning Began a Long Time Ago, In a Galaxy Far, Far Away From Florida: California"
“It is a period of chaos, delusion, early optimism and a false sense of security. The Cousins, scattered across California, have begun whispering of a grand vacation. No one knows where, when, or why… but one thing is certain: spreadsheets are coming.”

(Imagine that as a Star Wars intro crawl, with an awesome awesome John Williams score!)

Thanks for coming back to the Trip Report! Something to keep in mind is that we’re all based in California. Most of us are scattered throughout Southern California, pretty Los Angeles County heavy, with a few sprinklings in Orange County. Two of us are a medium-ish drive away up in the Bay Area, and one of us works right in the heart of Silicon Valley. Logistics were always going to be a thing to sort out, but the fun challenge we (really, for me) needed to plan!

The planning conversation of this trip really did started casually as a "we're due for another cousin trip". We had no clue that where we were going, or what we were gonna do. We were open to another WDW trip initially, but we thought we'd venture out and not limit ourselves. We had started the conversation in April of 2024, with no clue when we'd be taking this trip The sky was the limit, but we didn't think that the sea would be part of it too.

All The Ideas!
We tossed around the idea of Tokyo Disneyland and exploring Japan a bit. It sounded amazing until logistics and reality hit. Coordinating eleven people across the Pacific was tough. Then we remembered one cousin’s severe seafood allergy… in Japan. We shelved it for now. Not a “no,” just a “not yet.” Also, notice that number change? We didn’t realize we were going to be a dozen.

Then came Europe. Disneyland Paris hit our radar, and we figured, oh, that could be doable. Well, it didn’t score so highly in the many polls we took. It seemed like a great idea, but there wasn’t enough to do together. The focus was on spending as much time with each other as possible, while still leaving room for space and alone time when needed.

One thing led to another, and that’s when the word “cruise” started floating around. It seemed to offer both flexibility and built-in compatibility. Everyone could do their own thing without actually going anywhere, but still feel like they were going everywhere. It quickly became a frontrunner, even if we had no clue which cruise line, which ship, or which itinerary.

The first ideas tossed out were Alaska and Europe, specifically Norway. They sounded cool in every sense of the word, and adventurous too. But the only thing scarier than glaciers and fjords turned out to be the pricing and availability. Apparently, planning a year out was already too late.

So, we turned our gaze south. If we could survive Florida’s humidity, how bad could the Caribbean be? There was ocean breeze, there was air-conditioning, and there were plenty of options. When it came to cruise lines, we looked at every single one. The deciding factor was simple: no casinos and no cigarette smoke. And just like that, the choice became clear. Disney Cruise Line it was.

Which Itinerary?
We knew we wanted the longest trip possible, and boy did it end up being one in the end, but we thought a seven-night cruise felt just right. We had heard the less-than-stellar reviews of the Wish and wanted to bypass her shorter itineraries and limited offerings. The Treasure, on the other hand, was rolling out seven-night Eastern and Western Caribbean cruises… and the pricing didn’t seem too bad as long as we avoided the peak spring and summer vacation dates.

And just like Kendrick… Bing. Bang. Boom. A Seven-night Western Caribbean cruise for September 6–13, 2025 was officially on the board.

Oh, and this brings me to one of the many NPCs that played a huge role in keeping the cousins informed, Canva! Check out all the fun stops in this little slide I made on there:

It's confusing, but got the job done. Wait until you see all the countdown memes that helped us keep interest...

We Decided on a Cruise! …Now What?
We knew where we were going and what was going to happen along the way. But this was just the start of the planning. The logistics of getting there, the hotels (there were many considered, and eventually still quite a few in play by the end), and all the schedulable things were still ahead of us. Buddy, we were still more than a year out from this trip at this point. This was the easy part. The real planning was just beginning. Hang on, friends, for what I think is going to end up being a trilogy of planning.

(Cue the Star Wars–style John Williams outro)

Don’t worry, I’ll be back before you know it with everything that happened between the initial “we need a trip” talk and embarkation day.

 

[KJeff90]

Chapter 3 - “Live. Laugh. Logistics.”
Well friend, you made it back! As much as I want to go into painstaking detail about the planning process, there’s SO MUCH to go over. So in this post we’re going to go through “big idea”-bullets about major topics and milestones that happened through the pre-trip process, and a short description about what went down and what it led to. It’ll be a greatest hits of hijinks. I’m hoping it’ll share a unique perspective of planning a trip for a large party, and maybe help others in their efforts in the future.

With that said, the night we booked our cruise in May of 2024 left us with the start of our countdown:


That’s right, we booked this sucker well over a year out. This allowed for decisions to be made, flexibility, and mini disasters to bounce back from. Here we go friends, the topics are coming.

Disc0rd Discussion = Chaos Control Center
For our previous Cousin Trip to WDW, we used a Facebook Group as our primary way of communicating about decisions and updates. It worked… kind of. But it felt slow, cluttered, and not exactly built for the kind of chaotic energy we bring to trip planning. This time around, we upgraded. Enter: *******.

The Disc0rd server became our central command center — a beautifully organized mess of channels for every topic imaginable: resort debates, dining, excursions, countdowns, memes, and general cousin nonsense.



The chat format let us talk in real time, and the mobile app made it dangerously easy to pop in mid-workday with something like: “Okay but what if we switched the Falmouth excursion again?”

About once a month, we’d host full-blown Cousin Meetings. All of us would get on video or voice chat to coordinate major moves, compare screenshots, and even share screens to vote on plans together. It was part logistics, part comedy special.

In the end, Disc0rd was a total game-changer. We could compartmentalize conversations, share updates instantly, and keep everyone in the loop without the endless “did anyone see my comment?” spiral of Facebook. It was a case study in family communications with busy individuals.

Booking Together
Once we finally decided on the itinerary and the ship, the next challenge was figuring out how to book. Thanks to our newly established Disc0rd server, we pulled off what can only be described as a logistical miracle.

One late night, all eleven of us were online at the same time, fingers ready, browsers open, Disney Cruise Line website refreshed. When the clock struck, we booked one right after the other like a synchronized squadron of caffeinated travel agents. We were so coordinated that our confirmation numbers ended up being consecutive. We were in the Starboard, Aft; Staterooms 7656, 7658, 7660, 7662, and 7664.



And it gets better. When the dust settled, our staterooms were consecutive too, and they had connecting verandahs. Essentially, we created our own little village at sea: a stretch of staterooms linked by one mega balcony. It became our morning hangout spot and daily briefing area.

Every day, you could step outside and gradually see cousins appear one by one like a slow-motion roll. It was convenient, cozy, and honestly one of the best accidental decisions of the entire trip. Our own floating five-bedroom suite, complete with ocean views and a built-in sense of community. And don’t worry, we got privacy when we needed with those thick cruise ship walls.

Ezra Joins the Cousins
Originally, we had planned for eleven travelers. Somewhere along the long plotting process, exciting news arrived: Ezra was on the way!

By the time the trip rolled around, he had officially joined the crew, and everyone couldn’t have been happier. He added a whole new layer of fun to the planning process and a few new logistics to consider along the way.

There were details that needed special attention, from nursery reservations to mealtime planning, but everything worked out beautifully. In the end, our newest cousin traveler was about nine months old when he finally set sail, ready to charm the guests and crew of the Treasure. We got him on a training regime the moment he exited the womb to train for Jack Jack’s Diaper Dash.

Well, we ended strong with the introduction of Ezra...but this is just part one of the rapid fire logistics saga. There's too much to put in one post. So just like those annoying two-parter TikToks; stay tuned for part 2!

 

[KJeff90]

Chapter 4- “Live. Laugh. Logistics.” (Part 2)
To keep things organized, I split up the living, laughing, and logistic-izing (if that’s even a word). There’s still so much more to this story I need to tell you, and we haven’t even gotten to the part where the super secret side quest comes into play.

Until we get there, here’s more of the rapid-fire logistic bits from the planning saga!

Transportation Options: There Were So Many
Traveling with twelve people brought the fun challenge of figuring out how we would get around. We had multiple legs of transportation to plan for:

MCO → Hotel → Port Canaveral → Hotel → Airport

We considered everything: Lyft, Uber, Mears Connect, even taxis. There were literally 32 combinations discussed before we finally locked things in.

In the end, we primarily went with private transfers through Ace Luxury Transportation, using a 12-passenger sprinter van to and from MCO. For embarkation day, we used Disney Cruise Line transportation between our pre-cruise hotel and Port Canaveral. After the cruise, we switched back to Ace for the trip from Port Canaveral to our post-cruise hotel.

It ended up being smooth, comfortable, and surprisingly easy for a group our size. Ace really became one of the unsung heroes of this trip. At this point, we had not even booked our hotel stays.

The Before and After Hotel
Based on what’s often recommended on social media, and from personal experience with cruises in our group, we knew we’d need to book a hotel for at least the night before embarkation day. Some of us are known to get a little “land-sickness” after cruises, so we needed a place to recover on the tail end too.

Full disclosure, I work for a large hotel company that gives me discounted rates. So naturally, my first instinct was to prioritize properties within our 30+ brand portfolio for both our pre- and post-cruise stays. I went through so many hotels, weighing just as many factors: proximity to the airport, distance from the cruise terminal, number of rooms and beds, free breakfast… the works.

After considering enough hotels, villas, and timeshare properties to last me a lifetime, we finally settled on:

Pre-cruise:
2 Family Suites at Disney’s All-Star Music Resort
The Family Suites technically had enough beds for everyone (cozy, but it worked), had the Disney vibe we wanted, and came with the advantage of earlier boarding groups thanks to Disney transportation to Port Canaveral. It checked all the boxes.



Post-cruise:
A “Studio Commons” Suite at Element Orlando International Drive
I didn’t quite understand what this room type was at first, but it met all our needs. It had four bedrooms with king beds, a sofa bed, and a shared common area with a kitchen. Breakfast was included, which was a nice bonus. Even though my employee discount didn’t apply here, I booked a prepaid rate that saved us quite a bit off the rack price.



So, two hotels were chosen. For now.

There were a few plot twists that resulted in a change and an addition… but that’ll unfold later.

(In Patrick Warburton’s Voice), “Soon You’ll Be Airborne” …Kinda
The cousins and I are scattered all over California. The original goal was simple: book the same red-eye flight out of LAX to get to MCO. In theory, that did happen.

I booked the flight for Idahosa, Joseph, and me about six months out on Delta, planning to use SkyMiles to cover our luggage costs. The rest of the cousins booked their flights around four months out, all aiming for the same red-eye window. Then, literally the next day, we got an email.

That email threw us for a loop. The schedule change meant we’d need an extra night before our already-planned pre-cruise night, which wasn’t ideal for everyone’s work PTO limits. Because it was a departure time change of more than three hours, we had the option to refund the full amount to the original payment method. Just like that, the original bookings were erased, and we were back at square one.
In the re-booking shuffle:

• Katherine, Kelly, Daniel, Randy, Abbey, and Baby Ezra booked a red-eye with United.
• Albert and Kimberly booked with American.
• That left Idahosa, Joseph, and me flightless for the moment.

After some math, point calculations, and refund juggling, we realized it would actually cost less to add an extra hotel night at the Hyatt Regency Orlando International Airport than to force another red-eye. We’d use Delta SkyMiles to cover our checked bags and booked a morning Delta flight out of LAX that would get us into MCO by mid-afternoon two days before embarkation.

The new plan worked beautifully. We’d spend one relaxing night at the Hyatt before our cousins’ overnight flights arrived, then simply meet them at the airport for our transfer to the Disney hotel downstairs the next morning.

Well, that should sum up all the logistics for now. There are still a few plot twists coming up in later chapters, so stay tuned. Next up, I’ll be showcasing the wonderfully chaotic way I kept everyone engaged in our Disc0rd Server chat, and how it turned into a countdown comedy series of its own!

 

[KJeff90]

Chapter 5 - "Keeping Interest with Memes"
As you can see, there was more than a year of countdown time for this trip, so we had to find ways to keep things interesting and maintain excitement. It started simple: every ten days, I’d repost the countdown screenshot from the Disney Cruise Line app. That worked for a while… until we hit 150 days out. That’s when things escalated.

At that point, it evolved into full-blown meme updates every five days themed, dramatic, and usually tailored to whatever trip chaos was happening that week. It became part countdown, part inside-joke tradition.

Here’s a gallery of the greatest hits:

^^^ The Transition of Going from The Disney Cruise Line App Countdown Screenshots, and Highlighting "The Magic of Departing from LAX"


^^^ In the style of SNL Legend, Stefon (Fun read if you have the time!)


^^^ We hit all genres in these memes.


^^^ ...and current events.


^^^ IYKYK


^^^ Still waiting on the DuoLingo lessons for this guy's language


^^^ We were petty at times


^^^ The ever revolving cast of the Lazy Susan/spice rack all-in-one!


^^^ Ah, the weather...


^^^ Foreshadowing?! That's right, I used part of the thread title in this one!

That last post hints at a pretty major thing that happened. I’ll dive into what the plans were for that special day in the next post, and then later, what actually happened.

There are more twists ahead than an order of Cinnamon Twists from Taco Bell. Hang on, pals, this ride might get a little... bumpy. (Yes, that was a not-so-subtle nod to Indiana Jones Adventure at Disneyland.)

See you soon!

 

[DLo]

Following along . Looking forward to reading more . Very entertaining writing style .

 

[footballmouse]

This sounds like quite the adventure, I'm probably going to need 2 boxes of popcorn!

 

[summerlvr]

You've got me on the edge of my seat! Looking forward to reading more..

 

[alohamom]

And it gets better. When the dust settled, our staterooms were consecutive too, and they had connecting verandahs. Essentially, we created our own little village at sea: a stretch of staterooms linked by one mega balcony. It became our morning hangout spot and daily briefing area.

O?H MY GOODNESS! That is incredible!

Just like that, the original bookings were erased, and we were back at square one.

I got anxious just reading this but....

The new plan worked beautifully. We’d spend one relaxing night at the Hyatt before our cousins’ overnight flights arrived, then simply meet them at the airport for our transfer to the Disney hotel downstairs the next morning.

PHEW!

 

[KJeff90]

Following along . Looking forward to reading more . Very entertaining writing style .

Thanks! I really appreciate hearing this. I'm trying to capture the "in-the-moment" energy that happened during planning, and into the trip itself. Internal monologues get a little awkward, in a funny way, when they become external. I'm hoping we don't runt out of steam and that I maintain the same energy.

This sounds like quite the adventure, I'm probably going to need 2 boxes of popcorn!

We haven't even gotten to the good stuff yet! You sure it'll be enough?

You've got me on the edge of my seat! Looking forward to reading more..

Oh, there won't be a seat to sit on when everything starts coming at you. There's no time to sit! Glad you're coming along for the long haul though!

O?H MY GOODNESS! That is incredible!

The 5-stateroom setup really was a sleeper hit (both literally and figuratively!). I'll get into details about how it lead to some of the best relaxed moments in later posts.