On Becoming a Disney Person

And the itinerary that made it possible

Cinderella’s Castle, on film

A week ago to the minute we stood outside of the Four Seasons in Orlando, Florida waiting for the magic to begin. Our kids had been up for hours at this point, their eager minds knowing something special was about to happen. We got dressed in our well thought-out outfits (mickey baseball hats, prada ears, tweeny two piece set that still reads sweet), got through breakfast and convened in the lobby. Aaron, our VIP guide, walked up to the hotel at 8:25, pins in hand, excited to meet our family and share that he would be with us for the next three days. We buckled up (carseats provided) and got a backstage entry, straight into the Magic Kingdom, skipping Main Street and popping out next to the Castle.

For the next three days, I felt like a kid again. Perhaps what I most underestimated about this trip is that the magic that I assumed would be reserved for Elle, Jennings and George, was actually more special to me.

The things that made our trip were two-fold. Precise planning and knowing what we like. Because we had a VIP guide the planning step was less park logistics and what lightning passes to use when and more outlining outfits and accessories (diaper bags, pouches of snacks, etc.) ahead of time to maximize every moment and ensure we were prepared. The knowing what we like involved upfront intel: we would do Disney but not for dinner. We ate at the hotel every evening, returning once for fireworks (more on that below). For us, this provided a great outline of the day, and we could go hard (and skip nap) knowing what to expect (of our kids and for ourselves).

Here’s our outline (which was very fluid, but recapping so I can remember for next time). Read on for notes on what topped the list experientially.

Disney 2025, on film

Sunday Arrival at the Four Seasons

• Lunch at PB&G

• Pool Day

• Dinner at Ravello

Monday

• Breakfast at Ravello

• VIP Guide Pick Up at 8:30

• Magic Kingdom Park Day (Ride Plan Below)

• Dinner at Capa

• Fireworks from the Room

Tuesday

• Breakfast at Ravello

• VIP Guide Pick Up at 8:15

• Animal Kingdom & Hollywood Studios Park Day (Ride Plan Below)

• Early Dinner at PB&G at 5:15

• Minnie Van Back to Magic Kingdom Park Gate

• Dessert Party at 6:30 (Arrived Late, Which Was Fine); Get “Private” Fireworks Viewing Area Access

• Fireworks at 8; Left a Minute Early to Get Minnie Van Before the Crowds

• Minnie Van Back to Hotel

Wednesday

• Early Morning Snack in Hotel Room

• 7:20 Car to Disney Transportation Station (Tried for Minnie Van But Used Planned Car Service)

• 7:35 Ferry to Magic Kingdom Before Rope Drop

• Park Entry at 8:00, Went Straight to the Castle for Photos

• PARK TO OURSELVES! If It’s Photos You’re After Keep Walking Towards the Castle; Everyone Else Goes for the Ride Rope Drops

• Breakfast with the Princesses at Cinderella’s Castle at 8:35 (A Truer Park to Yourself Moment as You Get Access No One Else Does and It’s Magical)

• 9:45 VIP Guide Meet at Cinderella’s Castle

• Magic Kingdom Day (Ride Plan Below)

• 5:45 Dinner at Ravello

Thursday

• 8:00 Character Breakfast with Goofy, Mickey and Minnie at Ravello

• 9:30 Airport Pick Up

• 12:00 Wheels Up

Magic Kingdom Ride Plan Day 1, Made Possible by VIP Guide. I highly recommend!

• Peter Pan

• It’s a Small World

• Carousel

• Winnie the Pooh

• Little Mermaid

• Meeting Little Mermaid

• Dumbo

• Lunch

• Shopping

• Parade from Private Viewing Area

• Meet Mickey

• Train

• Buzz

• Cars

• Safari Boat

• Ice Cream

• Aladdin

Animal Kingdom & Hollywood Studios Ride Plan Day 2

• Animal Kingdom Safari

• Hollywood Studios

• Toy Story Mania

• Slinky

• Aliens Swirling Saucer

• Lunch

• Mickey’s Runaway Railway

• Planned Beauty and the Beast Show

• Snacks & Shopping

• Muppets Show

• Star Wars Rise of the Resistance

• Fireworks in Minnie Van

Magic Kingdom Ride Plan Day 3

• Breakfast with Cinderella 8:35

• Meet Cinderella

• Rope Drop Technically at 9

• Peter Pan

• Carousel

• Dumbo

• Barnstormer Rollercoaster

• Seven Dwarfs Mine Train

• Haunted Mansion

• It’s a Small World

• Lunch

• Bear Show

• Aladdin

• Tiana’s Bayou Adventure

• Parade

• Winnie the Poo

• Snacks & Shopping

What Topped The List

1. Our VIP Guide. The kids all said he was their favorite part of the trip. We got to ride everything we wanted (and more) and it was beyond helpful to have an expert leading the way so we could be present and ENJOY.

2. The Minnie Van / Fireworks / Dessert Party. Would definitely recommend doing this at least once.

3. Using a Disney Planner (recommended by our go-to travel agent). Our planner secured the guide, the dessert party and the Cinderella’s Table reservation. She was able to get additional dining but we opted out since we knew we’d want to eat dinner at the hotel. Not having lunch reservations kept our days more flexible which worked for us.

4. Our strollers. This sounds crazy perhaps, but having strollers that move and park easily was a game changer. Our cute stroller tags were also a win, and having a bag that easily clipped made stashing hats and cameras a breeze.

5. Disposable cameras for the kids. So special to capture this experience through their eyes. Not all the photos turned out (some dark) but that’s to be expected I suppose.

6. Pre-planned outfits and very specific packing. I am a notorious overpacking but for this trip I spent a lot of time on this (trying on every outfit beforehand and having Elle do the same) and it made getting dressed each morning a breeze. I got all matching outfits for the boys which also saved time and fuss and packed in our favorite Bitty Green Bags. Here’s everything we brought and wore.

7. Going in March. Not too crowded (perhaps because our spring break is early) and nearly perfect weather (a spritz of rain one morning, but we had ponchos which I ordered last minute, along with fans in case it was hot). Here’s our whole checklist of what to pack for the park.

8. Having the park to ourselves. If you want the photos with no one else at the castle and the right lighting, you have to get there when the gates open (which is different than posted park entry, since the rides aren’t going yet). For us, since we had an 8:35 breakfast reservation, we got in at 8 — we were on the way by 7:20, be sure to allot extra time for security and transport. There were also moments in the late afternoon that you could get close to the castle with no one else in the photos (around 3pm when everyone is lined up for the parade), but the sun was bright. We also had additional “park to ourselves” access because of that breakfast reservation - seeing the merry go round and behind the castle completely empty was a highlight for me.

9. Bringing our amazing nanny. It was a joy to have the person who is with the kids most (besides us) see their joy and experience the magic alongside them. It also worked well to have a 1:1 ratio for ride partnering given everyones ages/preferences.

10. Not overstaying - and leaving excited to return for more magic. Though we could have used one more day at the hotel (or in the parks, to see Epcot), there is something about leaving while you’re still on the high.

A week later as I sit and reflect…

I can’t wait to go back, which is *not* something I expected before our trip. Perhaps it’s my PTSD that made me think I didn’t like Disney (I had a miscarriage right after our trip six years ago), but I’m glad to have this experience as my most recent Disney World memory. The more I think about it, we did take Elle to Disney Paris (giving up a day in my favorite city) and I would like to get to Disneyland in California…so perhaps I have become a Disney person after all.

And, as for the shoes…the Substack is called Well Heeled after all…and I am, always, well, in heels (if I can help it). Day one was a flatform, day two was a comfortable sneaker-like elevated sandal and day three was a tried and true platform heel, similar here. Look good, feel good you know?