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 11/19!!
- Thread starter KJeff90
- Start date
KJeff90
Mouseketeer
- Joined
- Apr 1, 2011
- Messages
- 107
Chapter 6 - "#super-secret-side-quest"
Hey there, friends! Thanks for sticking with me. I know I left things on a cliffhanger last time, and this next post is one I’ve been both dreading and excited to share. So hang on to them hats and glasses, because we are diving into the most chaotic thing I had to plan for this whole trip… the proposal.
(In Jordan Fisher Voice a la Happily Ever After)
"Ready to Begin..."
Picture it. It’s late March-ish, and all planning momentum has stopped dead in its tracks. Flights are booked (probably too early, but it’s fine, that plotline changes later). We picked All-Star Music for the pre-cruise stay, we penciled in a post-cruise hotel, and now we’re stuck waiting for port adventure booking day. The Disc0rd chat? Silent. Almost too quiet.
So my restless little brain does what it always does… it finds something else to obsessively plan. And that “something else” was tiny. No big deal. Nothing stressful at all. Just… planning to propose to my boyfriend of 15 years.
It had been on my mind for a while; some may even say far too long. But regardless of how many years we’ve been together, this just felt like the right moment to finally ask the question. Sure, part of it was because I suddenly had nothing left to plan… but at the heart of it, there was something deeper. There was genuine love fueling this whole endeavor.
The ring may have been bought back in April for this September trip and proposal, but I needed every minute to plan for that special moment.
Who Do I Tell?
Aside from my boyfriend, I was traveling with ten other people (one still in the womb). So naturally, I had to loop everyone in on the fact that Operation Proposal was starting. Well… everyone except my brother. Bless his soul, but that man could not keep a secret if his life depended on it. Respectfully. Lovingly. Factually.
Which is how we ended up with a hidden Disc0rd channel for the cousins: #super-secret-side-quest. Literally all discourse went down here. Announcing that I was doing it, sharing plans, spiraling, revising, and of course… seeking validation from the cousins.
This was also when I realized it was ChatGPT’s moment to shine. It let me ask the questions I didn’t feel ready to ask anyone else. It helped me run through logistics when all the real people were asleep. And, most importantly, it kept my thoughts and plans organized when everything felt too big to hold alone.
The Planning Actually Begins
The [Disney] World was literally my oyster of opportunity to do this. With our redeye flight already booked, I technically had the better part of our one and only pre-embarkation day to roam around WDW and get the deed done. At the beginning, we didn’t have any park plans at all. The only thing locked in was the two Family Suites at All-Star Music. What’s funny is… all of that changed.
I knew I wanted something beyond the classic, slightly overdone proposal in front of Cinderella Castle at Magic Kingdom. No offense to anyone who’s done it, but the two of us don’t have any emotional connection to that castle.
If anything, I would’ve proposed in front of Sleeping Beauty Castle at Disneyland, a place we both actually worked and have history with. (Oh, did I forget to mention there was a point where we were both Cast Members at the Disneyland Resort? Yeah. That was a thing.)
I genuinely considered all four parks, the ship, the airport, and even the planes. If we were going to breathe the same air as it during the trip, it made the list of potential proposal locations.
One Thing Lead to Another, and Bing Bang Boom
Initially, I knew my boyfriend and I both had a very real, very deep love for Animal Kingdom. It is our kind of park: immersive, atmospheric, emotional, and honestly underrated. But even with that in mind, I kept straying away from the idea of buying a park ticket for just one day.
Why? Because all the usual reasons lined up one after another. The park closes early. We would be coming off a redeye, which meant a guaranteed late start and absolutely no rope drop. We already had a free waterpark day included with our stay at All-Star Music. And the biggest reason of all was simple: it costs more money. Every logical bone in my body (there aren't that many) kept saying, “Jeffrey, stop. Be practical. Don’t do this.”
So backup plan B came into play, still thriving on nostalgia and a desire to reach that happily ever after. I thought of the next best thing. We had always wanted to stay at Animal Kingdom Lodge, but never had the opportunity to. At this point I was not willing to spend more to visit Animal Kingdom Park, and I was definitely not going to splurge on a stay at the Lodge.
I remembered that iconic bridge in their lobby, and I thought it was the logical choice. I could just find our way to the Lodge and pop the question either before or after our waterpark day. Things were set.
But as you will see very soon, logic did not stand a chance. Who is she?
"It Wouldn't Be That Much More…"
Well, it seemed almost too easy to settle on that idea. It felt majestic and opportunistic if you will. But something kept irking me. It felt like I was missing something, like the moment I had imagined was not quite there yet. The sudden quiet with nothing left to plan was hitting hard, and my restless self kept wandering back to the internet looking for inspiration.
I kept wondering how I would even get to Animal Kingdom Lodge when a waterpark day and a stay at All-Star Music were already in play.
Curiosity got the best of me, and that is when I discovered Dave’s DVC Rentals. That is when I also realized the magic of booking through a third party and doing a points stay. Suddenly a three-bedroom Grand Villa at most DVC resorts was technically less than booking five Moderate Standard rooms at rack rate. Sure, we already had two Family Suites at All-Star Music with technically enough sleeping spaces to fit all twelve of us, but Disney trip planning math surpasses real math.
For only a “tad” more, and by “tad” I mean “double,” we could get a three-bedroom Grand Villa at a DVC property. So I put in the request for a one-night stay on the Dave’s DVC site and figured it would take a while to get approved. I had already come up with multiple backups, which I submitted in order of preference: Disney’s Animal Kingdom Lodge with Kidani Village as the top choice, then Boulder Ridge Villas at Wilderness Lodge, then Disney’s BoardWalk Villas.
Within about three days, it got approved. Before I knew it, I was paying in full for our three-bedroom Grand Villa at Kidani Village. And yes, it was significantly more affordable than the cash rate. Also don’t worry, I didn’t surprise my cousins with this new expense. I paid for this "upgrade" on my own. I told them about it well before we started the trip, so it wasn't an "in-the-moment" surprise. This is how I teased it to the cousins (...don’t get it? Neither did they).:
And all of this was simply to make the logistics a little smoother so I could get to that Jambo House bridge for the proposal.
"Oh Look, A Park Day Wouldn’t Be That Much More Either…"
Yeah, this restless mind also discovered that a day in the park for my boyfriend, my brother, and me would not be a deal breaker. So I did what any reasonable, responsible planner would do. I booked Animal Kingdom tickets for that Disney World day before embarkation. Sure, it was a “late start,” but I figured we could still get into the park by around nine in the morning, which felt like a perfectly doable day.
And of course I could not stop there. I kept going and booked this sucker:
I booked it for 10:30am in the morning, giving us enough time to grab a light breakfast and then head into the Capture Your Moment session. The plan was simple. Propose during the session and then celebrate with a more significant lunch right after. The cousins wanted to be part of the celebration too and suggested Jiko for dinner back at the resort after our day in the park and their waterpark day. We booked it for 7:20pm and 7:30pm (we had to split our party of 12 into two ressies). It seemed doable and it made sense.
This was also the moment where I took to the DisBoards community and asked for help, insight, and feedback. Here’s the post that grabbed interest from the community:
https://www.disboards.com/threads/ambitious-proposal-day-at-animal-kingdom.3971010/
About That “Significant Lunch”...
You would think planning a single meal after the proposal would be the easy part. You would be wrong. This is Disney. Nothing is ever that simple. What started as a nice, calm lunch idea spiraled into its own tiny side quest. For me, this became one of the most chaotic planning highlights. For others, it was the beginning of their villain origin story.
I had to reach out to ChatGPT for the receipts of our talks, but here are the stats of this not-crisis… crisis, lol:
The Plan So-Far (For Now…)
At this point, everything looked like it was finally falling into place. We had a park day, a Capture Your Moment session, a lunch plan that had survived too many identity crises, and a celebratory dinner that sounded elegant and calm. It was all coming together… or so I thought.
At this point, this is what we have planned for “Proposal Day”:
Hey there, friends! Thanks for sticking with me. I know I left things on a cliffhanger last time, and this next post is one I’ve been both dreading and excited to share. So hang on to them hats and glasses, because we are diving into the most chaotic thing I had to plan for this whole trip… the proposal.
(In Jordan Fisher Voice a la Happily Ever After)
"Ready to Begin..."
Picture it. It’s late March-ish, and all planning momentum has stopped dead in its tracks. Flights are booked (probably too early, but it’s fine, that plotline changes later). We picked All-Star Music for the pre-cruise stay, we penciled in a post-cruise hotel, and now we’re stuck waiting for port adventure booking day. The Disc0rd chat? Silent. Almost too quiet.
So my restless little brain does what it always does… it finds something else to obsessively plan. And that “something else” was tiny. No big deal. Nothing stressful at all. Just… planning to propose to my boyfriend of 15 years.
It had been on my mind for a while; some may even say far too long. But regardless of how many years we’ve been together, this just felt like the right moment to finally ask the question. Sure, part of it was because I suddenly had nothing left to plan… but at the heart of it, there was something deeper. There was genuine love fueling this whole endeavor.
The ring may have been bought back in April for this September trip and proposal, but I needed every minute to plan for that special moment.
Who Do I Tell?
Aside from my boyfriend, I was traveling with ten other people (one still in the womb). So naturally, I had to loop everyone in on the fact that Operation Proposal was starting. Well… everyone except my brother. Bless his soul, but that man could not keep a secret if his life depended on it. Respectfully. Lovingly. Factually.
Which is how we ended up with a hidden Disc0rd channel for the cousins: #super-secret-side-quest. Literally all discourse went down here. Announcing that I was doing it, sharing plans, spiraling, revising, and of course… seeking validation from the cousins.
This was also when I realized it was ChatGPT’s moment to shine. It let me ask the questions I didn’t feel ready to ask anyone else. It helped me run through logistics when all the real people were asleep. And, most importantly, it kept my thoughts and plans organized when everything felt too big to hold alone.
The Planning Actually Begins
The [Disney] World was literally my oyster of opportunity to do this. With our redeye flight already booked, I technically had the better part of our one and only pre-embarkation day to roam around WDW and get the deed done. At the beginning, we didn’t have any park plans at all. The only thing locked in was the two Family Suites at All-Star Music. What’s funny is… all of that changed.
I knew I wanted something beyond the classic, slightly overdone proposal in front of Cinderella Castle at Magic Kingdom. No offense to anyone who’s done it, but the two of us don’t have any emotional connection to that castle.
If anything, I would’ve proposed in front of Sleeping Beauty Castle at Disneyland, a place we both actually worked and have history with. (Oh, did I forget to mention there was a point where we were both Cast Members at the Disneyland Resort? Yeah. That was a thing.)
I genuinely considered all four parks, the ship, the airport, and even the planes. If we were going to breathe the same air as it during the trip, it made the list of potential proposal locations.
One Thing Lead to Another, and Bing Bang Boom
Initially, I knew my boyfriend and I both had a very real, very deep love for Animal Kingdom. It is our kind of park: immersive, atmospheric, emotional, and honestly underrated. But even with that in mind, I kept straying away from the idea of buying a park ticket for just one day.
Why? Because all the usual reasons lined up one after another. The park closes early. We would be coming off a redeye, which meant a guaranteed late start and absolutely no rope drop. We already had a free waterpark day included with our stay at All-Star Music. And the biggest reason of all was simple: it costs more money. Every logical bone in my body (there aren't that many) kept saying, “Jeffrey, stop. Be practical. Don’t do this.”
So backup plan B came into play, still thriving on nostalgia and a desire to reach that happily ever after. I thought of the next best thing. We had always wanted to stay at Animal Kingdom Lodge, but never had the opportunity to. At this point I was not willing to spend more to visit Animal Kingdom Park, and I was definitely not going to splurge on a stay at the Lodge.
I remembered that iconic bridge in their lobby, and I thought it was the logical choice. I could just find our way to the Lodge and pop the question either before or after our waterpark day. Things were set.
But as you will see very soon, logic did not stand a chance. Who is she?
"It Wouldn't Be That Much More…"
Well, it seemed almost too easy to settle on that idea. It felt majestic and opportunistic if you will. But something kept irking me. It felt like I was missing something, like the moment I had imagined was not quite there yet. The sudden quiet with nothing left to plan was hitting hard, and my restless self kept wandering back to the internet looking for inspiration.
I kept wondering how I would even get to Animal Kingdom Lodge when a waterpark day and a stay at All-Star Music were already in play.
Curiosity got the best of me, and that is when I discovered Dave’s DVC Rentals. That is when I also realized the magic of booking through a third party and doing a points stay. Suddenly a three-bedroom Grand Villa at most DVC resorts was technically less than booking five Moderate Standard rooms at rack rate. Sure, we already had two Family Suites at All-Star Music with technically enough sleeping spaces to fit all twelve of us, but Disney trip planning math surpasses real math.
For only a “tad” more, and by “tad” I mean “double,” we could get a three-bedroom Grand Villa at a DVC property. So I put in the request for a one-night stay on the Dave’s DVC site and figured it would take a while to get approved. I had already come up with multiple backups, which I submitted in order of preference: Disney’s Animal Kingdom Lodge with Kidani Village as the top choice, then Boulder Ridge Villas at Wilderness Lodge, then Disney’s BoardWalk Villas.
Within about three days, it got approved. Before I knew it, I was paying in full for our three-bedroom Grand Villa at Kidani Village. And yes, it was significantly more affordable than the cash rate. Also don’t worry, I didn’t surprise my cousins with this new expense. I paid for this "upgrade" on my own. I told them about it well before we started the trip, so it wasn't an "in-the-moment" surprise. This is how I teased it to the cousins (...don’t get it? Neither did they).:
And all of this was simply to make the logistics a little smoother so I could get to that Jambo House bridge for the proposal.
"Oh Look, A Park Day Wouldn’t Be That Much More Either…"
Yeah, this restless mind also discovered that a day in the park for my boyfriend, my brother, and me would not be a deal breaker. So I did what any reasonable, responsible planner would do. I booked Animal Kingdom tickets for that Disney World day before embarkation. Sure, it was a “late start,” but I figured we could still get into the park by around nine in the morning, which felt like a perfectly doable day.
And of course I could not stop there. I kept going and booked this sucker:
I booked it for 10:30am in the morning, giving us enough time to grab a light breakfast and then head into the Capture Your Moment session. The plan was simple. Propose during the session and then celebrate with a more significant lunch right after. The cousins wanted to be part of the celebration too and suggested Jiko for dinner back at the resort after our day in the park and their waterpark day. We booked it for 7:20pm and 7:30pm (we had to split our party of 12 into two ressies). It seemed doable and it made sense.
This was also the moment where I took to the DisBoards community and asked for help, insight, and feedback. Here’s the post that grabbed interest from the community:
https://www.disboards.com/threads/ambitious-proposal-day-at-animal-kingdom.3971010/
About That “Significant Lunch”...
You would think planning a single meal after the proposal would be the easy part. You would be wrong. This is Disney. Nothing is ever that simple. What started as a nice, calm lunch idea spiraled into its own tiny side quest. For me, this became one of the most chaotic planning highlights. For others, it was the beginning of their villain origin story.
I had to reach out to ChatGPT for the receipts of our talks, but here are the stats of this not-crisis… crisis, lol:
ChatGPT said:
The Plan So-Far (For Now…)
At this point, everything looked like it was finally falling into place. We had a park day, a Capture Your Moment session, a lunch plan that had survived too many identity crises, and a celebratory dinner that sounded elegant and calm. It was all coming together… or so I thought.
At this point, this is what we have planned for “Proposal Day”:
- Arrive at MCO around 6:00am.
- Meet up with our Private Transfer to Kidani Village at around 6:30-6:45am(ish).
- Get to Kidani around 7:30-8:00am(ish).
- Room won’t be ready, so drop off bags with Bell Desk and stop by the Front Desk.
- Maybe go to Sanaa for a quick breakfast, or at the Mara at Jamb House, for breakfast.
- Go our separate ways at 9:30am(ish). Cousins to Waterpark, My bro, boyfriend, and I to Animal Kingdom.
- Capture Your Moment at 10:30am. (Proposal Time!)
- Lunch at either Tiffins or Tusker House at 11:30? (Still figuring it out at this point).
- Spend the rest of the day in Animal Kingdom until 5:30pm(ish). The park closes at 6:00pm.
- Check into Villa at Kidani Village and get ready/dressed for 6:30(ish) ressies at Jiko to celebrate with the cousins.
- After dinner, go to bed and rest up for embarkation day.
KJeff90
Mouseketeer
- Joined
- Apr 1, 2011
- Messages
- 107
Chapter 7 - "The Great Upgrade Cascade" (Really, Just Part 3 of "Live. Laugh. Logistics."
Welcome back, friend! The journey continues, and we are sliding right into what should finally be the last chapter of the pre-trip shenanigans. I know it took us a minute to get here. Between real life, work chaos, and trying to post things at just the right moment (not too early, not too late, just right), keeping this thread updated has been an adventure of its own. Hakuna matata, the vibes for this chapter are easy, breezy, light, fluffy, and marshmallow-y?
Today, we are talking about upgrades. These were the delightful little “oh hey, that is nice” surprises that sprinkled themselves into the trip planning long before we even set foot in Florida. Nothing too intense, nothing too serious, just the fun glow-up moments that made our plans sparkle a little brighter.
Some of these upgrades were intentional. Some were accidental. Some were the result of things simply turning out nicer than expected. And some were a direct result of my own inability to leave well enough alone. (Shocking, I know.)
Either way, they all added a little extra magic to the journey. Let us get into the good stuff.
“The Real Treasures Were the Dining Reservations We Made Along the Way…”
Half of our traveling crew had never set foot on a Disney Cruise before, and the other half were only modest Silver Castaway Club members. Because of that, Palo availability was extremely tight and almost non-existent leading up to our booking window. It felt like all was lost for our large party, until we discovered the Private Dining Room at Palo Steakhouse.
^^ On My Way to Palo Brunch ^^
Instead of scrambling to grab individual Palo Brunch reservations for each stateroom the moment our window opened, I submitted the Private Dining Request Form on the DCL website for our group of eleven. (Ezra was not joining us.) The form stated that the dining room could accommodate up to ten guests, but I figured it was worth trying for eleven.
The confirmation timeline on the form said I would hear back within two weeks of embarkation. Instead, the reservation appeared in my plans about seventy-two hours after sending the request. It was easy, smooth, and surprisingly fast. Just like that, we were set for a 10:30 a.m. brunch on our second sea day.
Squeeze in a Date Night on Pirate Night?
Persistence pays off, and I am convinced a little pixie dust helped too. During the planning phase, I knew we would have our proposal and the full cousin celebration that same night. But I also really wanted a quieter, more romantic moment later in the trip to celebrate with Idahosa. At the same time, I did not want to miss any of the rotational dining on the Treasure. So naturally, I set my sights on the coveted Pirate Night Palo Steakhouse dinner reservation.
^^ A “Taste” of Our Palo Night ^^
This became my nightly ritual. I checked availability almost every night, usually after midnight PST, when fewer people seemed to be refreshing the system. After a few attempts and a lot of hope, a reservation finally appeared. Success. I secured a 6:30 pm Palo dinner for Pirate Night, just for Idahosa and me.
Bar Tours: The Adventure Continue
During my nightly skincare routine of checking the DCL website for activity availability, I found that there was a Cognac Tasting. I already assumed a happy little buzz (not of the Lightyear variety) would be happening at Palo, and the idea of keeping that momentum going felt perfect. So I booked it. The good times would keep rolling, and there was a decent chance we might be rolling around the ship too. The rolling happened, but wait until we get to that day in the trip report to see how it went.
From Flight Cancellation to Paid Flight Upgrade
The trip planning was definitely mathing. In the chaos of having our original red-eye cancelled, rescheduled, and then us getting a refund, and booking an even earlier flight… I decided to upgrade to a 7am morning flight in First Class. “A little bit more” seems to be a running theme in my enabling masterclass. That happened too. Bibbidi, bobbidi, booked.
Well friends, that is it for now. As you can see, all these little bits of planning, tinkering, and “just one more thing” moments are starting to add up to something with a lot of potential. In the next post, you will finally see the actual trip unfold. Chaos in planning is one thing, but just wait until you see the chaos of the trip itself. It will be a fun mix of blunders and blessings that caught us off guard and shaped the adventure in real time as we lived it. Stay tuned!
Stay tuned, stay hydrated, and stay ready. The next chapter kicks off at 3 a.m., because of course it does. I am not a morning person, yet here we are, starting in the dark, stumbling around my house, heading to the airport for a 7 a.m. flight like this is perfectly normal behavior.
What could go wrong?
(Everything. Obviously. See you there.)
Welcome back, friend! The journey continues, and we are sliding right into what should finally be the last chapter of the pre-trip shenanigans. I know it took us a minute to get here. Between real life, work chaos, and trying to post things at just the right moment (not too early, not too late, just right), keeping this thread updated has been an adventure of its own. Hakuna matata, the vibes for this chapter are easy, breezy, light, fluffy, and marshmallow-y?
Today, we are talking about upgrades. These were the delightful little “oh hey, that is nice” surprises that sprinkled themselves into the trip planning long before we even set foot in Florida. Nothing too intense, nothing too serious, just the fun glow-up moments that made our plans sparkle a little brighter.
Some of these upgrades were intentional. Some were accidental. Some were the result of things simply turning out nicer than expected. And some were a direct result of my own inability to leave well enough alone. (Shocking, I know.)
Either way, they all added a little extra magic to the journey. Let us get into the good stuff.
“The Real Treasures Were the Dining Reservations We Made Along the Way…”
Half of our traveling crew had never set foot on a Disney Cruise before, and the other half were only modest Silver Castaway Club members. Because of that, Palo availability was extremely tight and almost non-existent leading up to our booking window. It felt like all was lost for our large party, until we discovered the Private Dining Room at Palo Steakhouse.
^^ On My Way to Palo Brunch ^^
Instead of scrambling to grab individual Palo Brunch reservations for each stateroom the moment our window opened, I submitted the Private Dining Request Form on the DCL website for our group of eleven. (Ezra was not joining us.) The form stated that the dining room could accommodate up to ten guests, but I figured it was worth trying for eleven.
The confirmation timeline on the form said I would hear back within two weeks of embarkation. Instead, the reservation appeared in my plans about seventy-two hours after sending the request. It was easy, smooth, and surprisingly fast. Just like that, we were set for a 10:30 a.m. brunch on our second sea day.
Squeeze in a Date Night on Pirate Night?
Persistence pays off, and I am convinced a little pixie dust helped too. During the planning phase, I knew we would have our proposal and the full cousin celebration that same night. But I also really wanted a quieter, more romantic moment later in the trip to celebrate with Idahosa. At the same time, I did not want to miss any of the rotational dining on the Treasure. So naturally, I set my sights on the coveted Pirate Night Palo Steakhouse dinner reservation.
^^ A “Taste” of Our Palo Night ^^
This became my nightly ritual. I checked availability almost every night, usually after midnight PST, when fewer people seemed to be refreshing the system. After a few attempts and a lot of hope, a reservation finally appeared. Success. I secured a 6:30 pm Palo dinner for Pirate Night, just for Idahosa and me.
Bar Tours: The Adventure Continue
During my nightly skincare routine of checking the DCL website for activity availability, I found that there was a Cognac Tasting. I already assumed a happy little buzz (not of the Lightyear variety) would be happening at Palo, and the idea of keeping that momentum going felt perfect. So I booked it. The good times would keep rolling, and there was a decent chance we might be rolling around the ship too. The rolling happened, but wait until we get to that day in the trip report to see how it went.
From Flight Cancellation to Paid Flight Upgrade
The trip planning was definitely mathing. In the chaos of having our original red-eye cancelled, rescheduled, and then us getting a refund, and booking an even earlier flight… I decided to upgrade to a 7am morning flight in First Class. “A little bit more” seems to be a running theme in my enabling masterclass. That happened too. Bibbidi, bobbidi, booked.
Well friends, that is it for now. As you can see, all these little bits of planning, tinkering, and “just one more thing” moments are starting to add up to something with a lot of potential. In the next post, you will finally see the actual trip unfold. Chaos in planning is one thing, but just wait until you see the chaos of the trip itself. It will be a fun mix of blunders and blessings that caught us off guard and shaped the adventure in real time as we lived it. Stay tuned!
Stay tuned, stay hydrated, and stay ready. The next chapter kicks off at 3 a.m., because of course it does. I am not a morning person, yet here we are, starting in the dark, stumbling around my house, heading to the airport for a 7 a.m. flight like this is perfectly normal behavior.
What could go wrong?
(Everything. Obviously. See you there.)
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