Enjoying Disney World in January with a Five-Year-Old Girl

Oh boy, has an innocent family trip to Disney World become a topic of debate or what?

Camps are divided over whether a Disney trip is the family vacation of choice, to the point of it now almost existing as a subculture. Those outside this subculture often not-so-gently remind parents that for the costs and commitment of Disney, there’s an entire “real” world out there that children can explore through travel.

Personally, this is one where I love the middle ground. Yes, we love (and need!) slow, simple vacations and immersion into new world cultures through travel. But, we also LOVE Disney World and its magic and ability to put us into that child-like creative space where, like Walt believed, anything is truly possible with an imagination, some engineering and a little bit of pixie dust.

With that in mind, I’ve wanted to take my girl to Disney World since she was born. My grandfather and parents loved to take me growing up, and it was a travel tradition from my family of origin that I was excited to pass on. My two cents on Disney travel is there is a time, a place and a way to do it where it is experienced in its fullness before going down the (white) rabbit’s hole and everyone becoming exhausted and jaded. I waited patiently until my daughter’s fifth birthday - that time and place where I hoped a trip of this intensity would be exciting, memorable and magical to her but have her still at an age where I could control the experience and keep us all from being overwhelmed.

Spoiler alert: it worked.

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Since my girl is a Christmas Day birthday, it felt like a good way to (barely) offset costs of the trip and make the announcement a special memory by presenting the trip as a surprise from Santa, Mom and Dad. A new suitcase “all my own” has been the top of the list of desires for our girl, so she awoke on Christmas Birthday morning to a new Disney-approved suitcase filled with some second-hand costumes, Disney surprises and a letter from Santa with the exciting details.

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The timing also worked out perfectly where we could book our trip about 30 days out to let anticipation build and to travel at one of the record low attendance weeks for the parks. I partnered up early with a Disney travel planner, Small World Big Fun, who was a massive help with locking up our hotel and meal reservations. Meals seem to be the hot ticket item and I specifically had my eye on Cinderella’s Royal Table (inside Cinderella’s castle). My agent, Jody, looked for available reservations first and booked our trip around one available table left at the castle in the month of January (!!). From there, Jody was a massive help in working with me on an awesome itinerary based on what we wanted to be sure to do on the trip and our total budget. It was a huge relief to get the bulk of planning done over what felt like just a few emails, down to reservations for some of the best rides in the parks!

Another thing we took care of was getting PhotoPass, which is an package that allows parks employees to take your photograph at the parks with the images going straight to the DisneyParks app on your phone - with full photo rights for all images! Traveling as a little threesome, it was a great relief to know we would have all of the family photos we might desire (which was going to be a LOT based on my financial and time investments, k fam?).

Based on our daughter’s age and the length of the trip, we opted to just focus on Disney parks, side-stepping Universal, etc. and we stayed on the Disney resort at Caribbean Beach. We got a “preferred” room which put us about 60 seconds away from the resort bus stop and about three minutes from the lobby building. This seemed like small beans at the time of booking, but once we got on the property we noticed that some room blocks were a 10 minute walk from the bus! I would rate Caribbean Beach as just right for our needs on this trip - a cozy place to crash at the end of the day. If you’re bringing along smaller babies (that need a break at the hotel or in the rooms during the day) or grandparents, I might suggest going up one hotel tier. Disney hotels are rated as “value”, “moderate”, and “deluxe”, with Caribbean Beach being a moderate hotel. All of the staff at the hotel were excellent and accommodating and our room was spotless every day, which is all any of us required. Tip: The best part about staying at a Disney hotel are the free wake up calls from Disney characters! Just call in your wake up times and your phone will ring with a recording by a surprise character. Having the phone ring “for her” was such a highlight of the trip and she still talks about speaking with Winnie the Pooh on the telephone!

Since we were staying on Disney resort property, we took the Disney Magical Express bus from the Orlando airport to our hotel. This is such a nice cost savings (maybe “cost savings” is a bit of a stretch at Disney, but airport transfers are something I often overlook when budgeting our vacations and they can be SO expensive?! Not the case with the Magical Express.) and it’s extra helpful if you’re checking bags. Checked bags are magically picked up by special baggage handlers and then dropped off in your hotel room - so you can just get going without having to wait at the baggage claim or lug large, heavy bags upstairs with the kids in tow.

A few tips on this: Make sure you are wearing or carrying onto the plane everything you want to have with you for the first day! It can take half a day or so for the checked bags to make it to the rooms. There’s nothing like having to walk around all day in your flight clothes when you’re wanting to get into the spirit of the parks! Also, even if you plan to only carry-on bags and not check any luggage, I recommend still bringing the bag-tags that are mailed to you so you can use this service for transfer of your carry-ons from the airport should they get gate checked. We had a full flight to Orlando and our bags were gate-checked at our departure where I was very happy to realize I had the bag-tags in my purse - which meant we could avoid stopping at baggage claim in Orlando and instead got straight onto the bus to the hotel.

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We kicked off the Disney happenings with what I think is the best thing we did on the entire trip: Alice’s Wonderland Tea Party at the Grand Floridian Hotel (GF). The hotels themselves were such a marvel for our girl, it was fun to savor just that for a moment at the GF before getting overloaded with the parks! I made the tea party reservations in advance and for the cost (about $45) I thought the programming and surprises were above what I would expect if I were paying the same price for a similar experience at home in Dallas. The event is capped at 12 children, but our little girl was just one of two guests for the afternoon! Stories are still told in our home about the things that Alice and the Mad Hatter said, how they decorated cupcakes and drank Apple Juice Tea and designed their own tea set to take home. (Tip: We were headed out to one of the parks from here so the bell hop at GF took our teapot off our hands and sent it over to our hotel for us!)

This is also a children-only event - hallelujah! That left us parents available for a leisurely seated meal at the hotel to catch up and exhale from a long morning of travel which may have involved turbulence-induced child vomit. (There is a high tea at Grand Floridian at that time with champagne that looked Heavenly even though we passed on it, should you be inclined.) Everyone was really in vacation mode and feeling the Disney magic after this!

PhotoPass does the heavy lifting at the tea, since the kids enjoy themselves while a photographer takes care of getting photos that go straight to your phone.

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From here we went over to Epcot for the evening, which was a nice transition into the parks madness. The best part of heading over here from the tea party was traveling by Monorail! Epcot is a great half-day park if you logistically need one, like we did after arriving mid-day. By now we were up for just walking around to see the sights and we weren’t looking for anything so major that we had to do a lot of waiting (especially since we had Fast Pass reservations for the Frozen ride thanks to Jody!). The big show at Epcot for us was meeting Anna and Elsa. It was enchanting to see the generosity and friendship values of Disney Princess Lyfe already impacting our daughter, as she kept her floral bouquet and pinwheel from her tea party to gift to Anna and Elsa when she met them.

This was a day with a -gasp- costume change! Wearing costumes to the parks was not a thing during my upbringing, so I was trying to get on board and understand the ins and outs from a distance. Santa brought some costumes via Facebook yard sale and one Etsy semi-splurge with the news of the trip. I wore a backpack to the parks where I packed the costumes and clothing changes in gallon Ziploc bags. My girl simply changed from Alice to Elsa in the restroom at Epcot with no fuss.

Since we’re on the topic - I originally thought she would wear her Cinderella dress only to breakfast at Magic Kingdom and then change into play clothes, but I did not know at the time that every Disney cast member is required to call a child “Princess” or “Your Highness/Your Majesty” when dressed in costume. My favorite example of this occurred when we were all completely beat and walking out of Magic Kingdom at the end of the night when the park closed. As we were walking, two security guards got down on one knee and bowed to our daughter! It was worth tracking some princess dresses down, finding ones that I was on board with for photos and also packing an outfit change or two so she could get into the spirit. Even the way she carried herself walking through the park was more elevated in her costumes - princess manners!

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After the World Showcase, we had dinner at Seasons and loved Soarin’ and a few other rides before sitting down with some French macarons to watch Illuminations. A perfect first day!

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Magic Kingdom was the big show and our destination for our first full day at Disney. Planning this for the second day was great for us as we still had lots of energy and were feeling transported into a magical world where everything registered high on the WOW factor. We got in right as the park opened and headed to the castle so we would have plenty of time before our 10:00 a.m. breakfast reservation. We did not do the Bippity Boppity Boutique, but I had heard a rumor that the Castle Couture shop right by the back side of the castle would pixie dust your hair on the house. Our daughter loved this! We also had time to ride the carousel which was a really nice way to take in the park and get jiving. Right in front is the Sword in the Stone which I love for photos. We even saw a boy pull the sword out!

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Choosing to experience the magical and special feeling of dining inside Cinderella’s castle was a no-brainer for me - especially for a little girl’s trip where the alternative way to have the same experience was to wait in line to meet a bunch of lovely 20-year-old college interns dressed as princesses. Instead of dealing with butterflies and trying our collective patience waiting in line, I’ll take checking celebrity meet-and-greets off the list while seated and eating.

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From there it was all of the best park stuff, from Pineapple Dole Whip to Dumbo and fireworks. The creature of habit that I am was quite pleased.

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On the morning of our second full day at Disney, we were completely beat - our daughter had fallen asleep standing up on the bus the night before! We were also relieved that after two days of early mornings and late nights, I hadn’t made a reservation for this day until noon, so we were in no rush. We still woke up early and got to Hollywood Studios, rushing straight to the back corner for Toy Story Land.

Slinky Dog Dash was the only ride I was not able to get on FastPass before the trip so we headed there first and had our only hour-long wait of the trip. I’m still surprised to say, we enjoyed it. It’s so easy to shortcut and plan out every minute of a day here - but we enjoyed actually needing to stand around a little and pass the time, making conversation and letting anticipation build. The details in Toy Story Land are bananas and this was our daughter’s favorite ride by far. We even lined up later that evening to ride again and almost did it three times! So with that said, I wouldn’t write off an attraction just because it’s not available for you to FastPass!

Hollywood Studios was a great third day park for us. Our five-year-old is too short to ride a few of the rides at Animal Kingdom, but she could ride Tower of Terror (which impressed me!) and the Toy Story rides, so Hollywood Studios seemed like a more age-appropriate choice of park for this trip. This was also my favorite park when I was little and I am selfish. Logistically, with this park being smaller and featuring more show-based attractions, it made sense for our tired feet! It was a leisurely day that helped us wind down our trip. I also can’t believe that it will have the Star Wars land there soon, so I wanted to soak up the kind of old school vibe of the park before it gets too crazy with the addition. Our daughter did not know what to make of the Star Wars attractions or shows that were there at all, and she was switching back and forth between reactions of curiosity and being freaked out. Now all she asks us to play at home is the Star Wars musical score and she is obsessed with Chewy!

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The last day we had an evening flight, so we had a leisurely wake up at the hotel and went to Disney Springs for lunch and poking around before our flight. This area has changed so much for the better! The shopping is great and we loved Raglan Road Irish Pub. It was lively, even at Sunday lunch, so it didn’t feel like a downer way end to vacation. The Irish performers are great and even invite the kids on stage! The gluten-free fish and chips were the best I’ve ever had.

Our energy as a family on the flight home and over the next weeks was so vibrant and connected! This was just the perfect amount of time for us to peek up from our New Years routines and winter to do something fun and commemorate such a special milestone - going from toddler to little girl. We are so proud of our daughter and this trip and all of the sacrifices, planning, and even figuring out a new app (if you’re at Disney your life is run by the Disney app) was completely worth it to us. It was also a great conversation starter for our family on the magic of making joy for others, saying thank you and practicing gratitude, using our table manners and patience - all things that I’m focusing on as we get ready for Kindergarten!

Share your favorite Disney memory below or let us know what we need to do next time!

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