Start With WHY
If you are coming from the Start Here Series, welcome. This is the long version of Question #1
Before you look at a single resort photo, answer this one.
The question I get most is "which resort should we book?"
It is the wrong place to start. Not because it does not matter, but because it is an answer, not a question. Same with how many days you go, whether you park hop, and what you are willing to spend. Those are all downstream of one thing you might not stop and think about.
Why are you going?
What I actually mean by WHY
I do not mean "because it's Disney." That does not count.
I mean the purpose of this specific trip, the one you have in mind right now. What are you and everybody coming with you hoping to get out of it?
Maybe it is:
your kid's face the first time they see the castle
celebrating something big
riding everything, twice
actually resting. Yes, at Disney. It is possible.
I know this sounds obvious. But you are putting real time and real money into this trip. Taking twenty minutes to figure out what everyone going actually wants from it is what makes every other piece fall into place.
Same parks. Four different WHYs.
Four completely different trips.
Here is what I mean in practice. These are four real trip types, and they should not look alike or cost alike.
The bucket list trip
WHY: One big trip while the kids are still little.
You are treating this as a do-it-all-the-way trip. So stay on the Monorail. Go for a full week. Hit every park, some of them twice. This is the one where you spend the money, because the whole point is that you are not planning to repeat it for a while.
If this is your WHY, this is the time to stretch the budget when picking a resort. Proximity is the thing that saves you when a 4 year old melts down at 5pm and you need to be back in a hotel room in fifteen minutes.
The birthday trip
WHY: It is about one kid.
Pick the resort that matches whatever they are currently obsessed with. Build every day around them. Spend on their big moments and skip the rest, because nobody else's preferences are driving this one.
Everyone else is a plus-one this time, and that is allowed.
The girls trip
WHY: Adults, snacks, zero nap schedules.
Off-site or something in the Epcot area, long weekend, done. Less money on the room, more on the fun. Though make sure you think carefully about the how many beds you need!
You do not need a week. You need three days and good shoes.
The multi-gen trip
WHY: Grandparents, cousins, the whole crew.
Look into a DVC rental. Kitchens, room to spread out, and doors that close. Usually more space for less money than booking three hotel rooms.
I will say this louder for the people planning a big family trip: everyone needs a door that closes. Every single one of those relationships survives the week better because of it.
My recent WHY, for an example
My last trip was my 10th wedding anniversary celebration with my husband. No kids. My husband had wanted to stay at Animal Kingdom Lodge for over a decade. We went in July to get a deal for Club Level.
So the WHY picked everything: four nights, club level, savanna view, and dinner at Victoria & Albert's.
Was that how I would book a normal family trip? Absolutely not. It was the right call for that WHY, and it would have been the wrong call for almost any other one.We hit our favorite rides, ate our favorite food, then otherwise focused on resting and the silence of an adults only trip.
See the pattern?
In every one of those, the WHY picked the resort, the length of the trip, and where the money went. Not a ranking. Not a Facebook group. Not a stranger named Deb who is VERY sure.
Which is why this is a conversation, not a solo journaling exercise. Have it with your spouse, your older kids, whoever is in your travel crew before you do anything else. Seriously, before anything else.
Ask everyone who is coming:
Who is this trip really for?
Is this once in a lifetime, or the first of many?
What does a great day look like? Rope drop to fireworks, or pool by 2pm?
What is the one thing that would make the whole trip worth it?
You will find out fast whether you are all planning the same vacation. Better to learn that now than when you are trying to convince someone to wake up for rope drop when they want to sleep in.
And to be clear, this works for any trip. Not just Disney.