ProphetPaul’s Planning Process - Part 1 - Proposal

This is a follow up to A Dream Delayed and Paul’s Dream is Renewed. The last year or so has been pretty crazy for me and I’ve found that writing has been therapeutic. So, I decided to write all my pre-trip planning thoughts down and share them here. It’s a lot, so I don’t expect anyone to read all of it. However, I do love the feedback from this wonderful community, so please share your thoughts. This first post will just cover the context of our trip and the process of deciding when to go, how long to stay, etc. My next big post will go into the actual itinerary and daily touring plans.

Hello, my name is Paul, and I am an addict. A Disney Addict. I’m a 33 year old man and I’m not ashamed to say that my favorite movie is Beauty and the Beast. My radio almost exclusively sings Disney, and I wear Mickey Mouse pajamas to bed (see proof below). I grew up during the Disney Renaissance and the stories and music became a part of me. Despite this, I first considered a trip to Walt Disney World (WDW) less than a year ago*. The idea started like a dim candle at the end of a long dark hallway, but a moment later the house was on fire. Visions of WDW engulfed me like an inferno. Why had I never thought of this before?!?!

*I’ve been to WDW once when I was 16, for a few hours. I remember riding Splash and Space. That’s it. So, I consider myself a first-timer.

It happened in May of last year. My youngest son (DS2) was battling cancer (he’s in remission now, thank God), and at some point I offhandedly threw out the idea of going on a big trip to coincide with the end of his treatment. We could also celebrate our 10-year wedding anniversary and our last trip as a family of four (we expected DD in December). So, I decided that we should do a big trip. And not just any big trip, but THE big trip. With 2 very young kids and another on the way, the first thing that came to mind was Disney World. I mean, what could be better?

Apparently, fate agreed with me. The next evening was my turn in the hospital with DS2, and guess what played on the TV – Beauty and the Beast! I hadn’t seen it in years, and it brought tears to my eyes. My life was upside down, but for a few hours I enjoyed the Magic. In fact, the Magic filled me up and I couldn’t stop thinking about WDW. Soon afterward I began the initial research for our trip – when to go, where to stay, how long? All these big questions led me to places like the TP forums.

I quickly realized that I needed to start putting together some ideas and notes, and organizing it all in some way to show DW. My “go-to” for this is a mix of Excel and Powerpoint – pasting screenshots, tabulating data, etc. I’m a data connoisseur, a maven. I love compiling masses of information and distilling it all into a narrative for others to follow along. I also really enjoy graphic design, especially maps and infographics. I usually go overboard with it. Here’s the cover page I created for my “ideas and notes” Powerpoint:

Planning a trip to WDW became a solace for me – it allowed me to focus on something other than cancer for a little bit each day. Unfortunately, it was another source of stress for DW, and my 10-page “Proposal” produced a look of horrific anxiety on her face. She said she would just rely on me to make some of the decisions.

The big trip was scheduled for late October, but due to complications from DS2’s surgery and DW’s pregnancy we decided to postpone it until 2019. Although that 2018 trip didn’t happen, nearly all the research and documentation I put together could be used for 2019, albeit with some tweaking. During the last few months of revisiting my trip ideas, I have come to believe strongly that this year is better all around for all of us. It is going to be awesome.

Now, we begin with the same big questions I had in 2018…

Why go to WDW?

To be completely honest, it is my strong personal attraction to Disney that is leading us to WDW; I really don’t need any other reason. I love Disney and I want to be immersed in the Magic. I’m sure I’m preaching to the choir here.

However, to convince DW that this is the year to do it, I put together the following List of Justification :

  • We haven’t been on a real vacation since DS4 was born in 2014 (we used to do 1 or 2 big trips each year)
  • DS2 is cancer-free (this trip is really for my sons, DS4 and DS2, who have been through Hell this last year)
  • Missed opportunities last year for 10th wedding anniversary trip and last “babymoon”
  • DW’s 10-year mark at current job (next year)
  • My 5-year mark at current job (this year)
  • DS4’s last year before Kindergarten (last chance for big off-season trip)
  • We’ve survived 3 infancies (hopefully still true in a few months, haha)
  • This year it’s possible to do MNSSHP on Halloween, run in W&D Races (I’ve become a “runner” this year), and do MVMCP all on the same trip (more on this point later)
  • Lowest crowds until 2022 or later (SWGE opens, then WDW 50th anniversary).
  • We can afford the financial hit (especially since our “vacation fund” has gone unused for 4 years)

All of these reasons put me in the mindset of wanting to splurge on our trip – spare no expenses. Club level? Yes please! Early Morning Magic? Heck yeah! However, DW is much more conservative financially and nearly had a heart attack when I showed her my cost estimates. So, she has reigned me in. A little. She makes some good points - mainly that our situation is different now than a year ago. We will have significant ongoing medical expenses for DS2 going forward, and many of our other expenses will be higher as well now that DD has arrived. Do we really need TS meals every day? Is the Fireworks Dessert Party really necessary? These will be the debates I will have with DW over the next few months.

In any case, I easily justified going to WDW this year. This leads us to the next big questions…

When to go, how long, and where to stay?

When planning the 2018 trip, we were limited in time to after DS2’s surgery (August/September) and before DW was too pregnant to travel (November), leaving just October. I got really excited about that timeframe as the crowds aren’t too bad, and MNSSHP sounded like a lot of fun. What could be better for the boys than trick-or-treating at WDW and getting to meet some villains (Scar and Jafar are DS4’s favorites)? Temperatures are reasonable and it’s at the very tail end of hurricane season. The Food & Wine Festival is still going on. Lots of good reasons to like this timing.

For the rescheduled 2019 trip, I immediately started looking at the same time of year. However, since we had a lot of flexibility this time around, I was looking at everything between the week of Fall Break (Columbus Day) and Christmas. The MVMCP sounded just as fun as MNSSHP, so I kept that option in mind. Ultimately, I had about 4 or 5 candidate timeframes to compare. The decision was guided by the answers to five questions:

  • Should I run in the Wine and Dine Races? Emphatic yes! As a way to cope with the stress of childhood cancer (DS2), and an unplanned addition to the family (DD), I started running last year. My goal is to run a half marathon in 2019, and when I found out that there was a chance to do this at WDW around the time of our trip, I was thrilled. I was so excited that I booked a 2-night stay at All-Star Sports, just in case the family trip didn’t work out. Not only do I plan to run the half, but also the 10k (the “Two-Course Challenge”). A secondary question for this was whether to plan the trip so that the races were at the beginning or end. I decided that ending the trip with the W&D was better – starting off a trip sore and exhausted sounds awful.
  • Should we attend a MNSSHP? Yes, simple as that.
  • Should we attend a MVMCP? No; however, my initial “Plan A” had us starting with MNSSHP on Halloween, then running W&D races, and ending with MVMCP (remember that cover page I showed you up above?). Sounds awesome. Also, utterly exhausting. Additionally, MVMCP at the beginning of November would feel out of season to me. It would certainly feel odd to celebrate Christmas at WDW, then be home for a few weeks before Thanksgiving. I eventually decided that this was a “no” for me, even though Christmas is my favorite holiday.
  • Should we spend Halloween at WDW? Yes, it will be more fun than at home.
  • Should we bring DD1 with us? When I first started thinking about the 2019 trip, I was 100% against bringing a 1yo with us. I figured it would put a huge damper on the trip. But then our daughter was born and I fell in love with my little princess. Now, I can’t imagine leaving her at home for a week while we’re in the World. So, she will be coming with us. Yes!

Our answers quickly put us at Halloween week or the following week. We used other relevant information to make our final decision, including WDW events like Food & Wine Festival and SWGE opening, family events, and … duh duh duh … crowd levels. I took a unique approach to comparing crowd levels across the October-December timeframe. I compiled KtP’s predicted CLs (converted to a 1-10 scale) and TP’s reported “actual” CLs from the last 3 years. For each, I matched up the 3 datasets by weekend (e.g.,the 1st weekend of October in 2016, 2017, and 2018 was matched up) and then took the average crowd level for each day. If anyone wants to see how I did this, I can share that info in a different post. You can see some of the result in the chart below. This method worked well for me, at least to quickly see that Halloween week was significantly less crowded (historically) than the following week, “Jersey Week”. This solidified my opinion that it would be better to tour WDW first (during Halloween week), and then run the W&D races at the end of the trip.

Next, how long should we go? This is our first trip to WDW, and I don’t envision us going back for at least 2-3 years, considering the craziness that is going to be SWGE and WDW 50th. With that in mind, I want to scope out a large majority of the World, and get a good feel for what we would want to do on future trips. Here is my wish list:

  • explore all 4 parks, monorail resorts, WL, FW, and the Boardwalk area
  • at least 1 TS in each park, plus 2-3 resort TS, with emphasis on character dining
  • Hoop-Dee-Doo
  • Disney Springs: PhotoPass Studio (in Halloween costumes), Raglan Road, Aerophile
  • Pirates and Pals Fireworks Cruise
  • Fantasyland Early Morning Magic (EMM)
  • Toy Story Land EMM
  • W&D Expo and races

That’s a lot to do in one trip, and we’ll have 4, 3, and 1-year olds with us, so we can’t be doing RD-to-close kind of days. Naps will be necessary, so we will have long afternoon breaks out of the parks (except for possibly one day when we switch hotels). We’ll just have a double stroller, so either DS4 or DS3 will be walking, meaning our walking pace will be slow.

In order to figure out how we could do everything on the list, I spent quite a lot of time playing around with my itinerary (see simplified version below) and custom TPs. In my next big post, I will go into a lot of detail on the itinerary and TPs, including the process of developing them. The point for now is that after a few weeks of fine-tuning, we’ve finally got a plan that packs almost everything on our list into about 8 days: 4 in MK, 1 each in the other parks, and 1 for other stuff.

Now to the final question: where should we stay? You’ll notice in the itinerary above that we are staying at the Contemporary (CR) for the first 4 nights, and then the Boardwalk (BW) for the last 4 nights. The primary reason we chose these hotels is that we will be able to walk to the parks during most of our trip: CR to MK, and BW to HS/Epcot. These hotels also have other transportation methods available besides the buses (and Lyft): monorail and boat for CR, and Skyliner (if it’s ready) and boat for BW. I know my sons will enjoy the diversity of vehicles we’ll ride on this trip:

  • Airplane
  • Bus
  • Monorail
  • Gondola
  • Boat
  • “Minnie Van”
  • Hot Air Balloon (Aerophile @DS)

I know that last one is a stretch, because it doesn’t really transport you anywhere. I’m leaving it anyways. It’s unique.

Getting back to hotel choice. Since the beginning, the plan was to stay at CR. Since our biggest focus will be on MK, the convenience of walking there was the deciding factor. It also provides boat service to WL (on my list of must-see resorts) and FW (for Hoop-Dee-Doo). The Pirates and Pals Fireworks Cruise departs from the CR. To save money, we are booked in a garden view room in the garden wing.

Originally, we were going to spend all 8 nights at CR, but while doing some more research I really started to like the Boardwalk. Walking to/from Epcot and HS is possible, with boat service to these as well, and the Epcot Skyliner station will be very close by. Lots of options. It’s also on the Wine and Dine course, so my family can cheer me on without having to go anywhere. Once I found out these key points, I was sold on the BW for the last 4 nights of the trip.

Well, I’ve run out of gas, so that’s it for now. We’ve decided when to go to WDW, how long we’ll stay, and which hotel(s) will be our home away from home. The next big post will focus on our itinerary and daily touring plans.

Thanks for reading!


Love this…so excited for your family…you deserve it!


One of the things that’s fascinating to me is how complex planning a WDW trip is. In maths terms, you’re solving many simultaneous equations in many unknowns.

It occurs to me as I write this that part of the reason not everyone plans in the way that I do is because they can’t. They literally don’t know how. Even assuming they’d want to.


So what is the equation? Come on…blind us with science! :blush:


As the WDW proposer/planner in my family, I love all of this. I might even make a few changes to my standard planning spreadsheet based on some ideas I’ve gotten from yours.

I’m really happy your family will this time together at WDW after all that you’ve been through.


This was deeply satisfying to read. I can’t wait to read more!


I loved reading this! We went to WDW December 2018 and I am already trying to talk my husband into going back. I told him that I could wait until 2020, but I think your post and information has me thinking we should go 2019 as well. I might need you to convince my husband for me!! He complains about my Disney addiction to his coworkers.


Another important factor is time. It takes a lot of time to plan a trip like we do. Most people don’t have that time or are unwilling to sacrifice sleep.

More to your point - one of the reasons I’m sharing my process here so openly is to give people some tools for planning. How to make decisions. How to organize your thoughts. I’m not as good a teacher as I once was, been out of practice for a while now. But hopefully everyone learns a thing or two from this series.


Can you rent a second single stroller? I think this will really slow you down and negatively impact the trip (and cause you to miss many attractions). My 3.5 y/o daughter rarely uses the stroller when we are in our hometown, but she spent a substantial amount of time in the stroller at WDW. There is a ton of walking between attractions. Also, you or your wife may want take the 1 year old back to the resort for a midday nap while the others are at the park (or may be napping while everyone else is ready to get back to the park). It would be nice if both groups had a stroller. We rented 2 single strollers and it wasn’t that expensive (and the stroller rental company delivered it to and picked it up from CR).


Impressive planning…

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This is definitely being considered. It kind of depends how DS4 is doing closer to trip time. Now, some days I think he’d be fine but others I’m not sure. Thanks for your input!

Looks like DH and I will be there most of the same days as your family; I don’t run anymore, but will look for you and cheer you on!

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I love seeing everyone’s planning, thought processes, and especially the spreadsheets. My plans and proposals are no where near as detailed as yours. I read these planning posts and I feel like I have found my people.


Hear Hear!


Terrific report! Love that heatmap sheet.

Also, don’t want to burst your bubble if you didn’t notice already, but they put the letters on your Mickey Mouse PJs backwards. :wink:




NOOOOOOOOOOOOO! :slight_smile:

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This is great! I love the way you’re breaking everything down!

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I’m thrilled that you and your family will be getting to make this trip this year! Hooray for son’s remission and congrats on your new baby girl! This new plan does seem superior to last year’s trip plan.

I look forward to reading all your posts!

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Me too!

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