In which we take a preschooler, two toddlers, and an infant to Disney World

“Brave” was the adjective most utilized when we shared our pictures from the trip. “Crazy” was the adjective used by my husband when I asked him if he thought it would be feasible to take Ruth to Disney World for her fourth birthday. So, I let it lie. But right before our annual trip to Florida to visit Scott’s family near Orlando, I got in touch with our dear friend (who lived next door to us when we were in law school) who works at Disney and asked him whether he thought I was out of my mind to hope to take Ruth to Disney. “Not at all!”, he responded. “Head on over, and we’ll take care of you.”

So, we made it happen. Cody’s (our friend who works at Disney) wife happened to have the day off, and she met us at the gate to help us out with the girls. Scott’s aunt and two cousins (who are much younger than Scott) were also able to come with us and help. Scott’s cousins (two boisterous little boys) patiently went on every baby ride with us without complaint and were so kind and attentive toward the girls. All of our companions for the day were a blessing to us for sure.

The magic carpet ride was about as thrilling as it was going to get ride-wise for these two patient kids.

A few people have asked for tips on doing Disney with babies and toddlers. Welp, I have done it all of one time, and I think we had such a fabulous experience due mostly to luck, but I can share what worked for us this time.

  1. Bring help, and preferably someone who is familiar with the park. We were fortunate in that Scott’s aunt was very familiar with the park, living nearby, and Cody’s wife Rebecca was pretty much an expert on all things Disney World. It made things so much easier having a tour guide who knew the rides, the places to eat, and what wait times were good and bad. (She even knew when to protect the volatile toddlers from sudden water squirts on rides!) We had an adult for every child, which also helped with rides that only seated two or three at a time, or rides that I would have to sit out with the baby.   
  2. Have a plan for transporting the babies and young toddlers. I wore Rhea, which worked really well, even though it was beastly hot. I had a little paci stashed in my Ergo for when she got fussy, and she pretty much just napped the whole time. All of the rides we went on had no problem with me wearing her, with the exception of the carousel. I had to sit with her on my lap in the carriage. Go figure.  We also used a small, lightweight stroller for Wren. You can rent strollers there, but they were large, plastic, and unwieldy. Wren stayed in it without complaint until it got too close to nap time and she wanted to be held. Then we put Rosie in it.  

Stroller shown here. It holds up to 50 lbs and Rosie was pushing that limit.

3. Go in the off-season. The cognoscenti  inform me that November is the best month. The park is empty and the weather is lovely. The park was pretty empty when we went (on a Tuesday in late September) but it was HOT! The wait times for rides were only 10 minutes early in the morning and about 40 minutes in the afternoon. We didn’t use them, but I’ve heard fast passes are worth it for the rides and the characters you really want to see. 


Hot, y’all. And this was in late September! Can you imagine what it is like in the dead of the summer?!! Heat stroke city.

4. Keep your expectations low. You won’t get to do all of the things you want to do (it seems like the options at Disney are ENDLESS)  and the toddlers will start to melt down if you stay too long. We left the second Wren started fussing and managed to avoid any major meltdowns. Because Magic Kingdom is pretty far from parking, and we had to ride the train, then the monorail, and finally do a good bit of walking just to get back to our car.  I’ve heard the other parks are easier. 

5. Get your pins! Once you arrive on Main Street, you can ask a friendly representative for pins commemorating your children’s first visit to Disney. They helpfully write the date on the back. Ruth got another pin for her birthday too!

  Only Rosie could be surly in front of her beloved Cinderella’s castle at Disney World.

6. Miscellaneous. Don’t bring selfie sticks. Apparently those were causing some major problems and are now banned. I don’t know why, but I find that hilarious. Selfie stick duels! Also, if you are an adult, do not dress as one of the characters. It is confusing for all of the children.  We saw a Cinderella imposter getting a citation for that very offense. 

The girls really did have a marvelous time (we even got a few smiles and giggles out of Rose!). Ruth will tell anyone that will listen about Disney. She even remembers every character that just happened to walk by us (“Chip and Dale and an Aristocat!”) It was the trip of a lifetime for us. We are incredibly beholden to our dear friends and family who helped make it happen.

And now for the photo dump: 

 Real men wear babies. 

 Wren is too cool for the rest of us. 

 Instead of the flattering “skinny arm” pose, I opted to let it dangle awkwardly. And this, my friends, is why we can’t have nice blogs. 

I’ll probably bore you with all of the minutia of the rest of our Florida trip in another blog post or five. You have been warned.

Have any of you taken your littles to Disney? What advice would you give? We are definitely going back. Even Scott has been bitten with the Disney bug after our enjoyable trip. 

19 thoughts on “In which we take a preschooler, two toddlers, and an infant to Disney World

  1. sarah isis (@disisd)

    Oh hey! I want to “borrow” this family photo Bec that’s where I breastfed Lucy in front of hundreds. And nobody was there to take a picture for me to remember it. Lol.


      Ha! I breastfed Rhea all over the park too since she was only four months and in the Ergo.

  2. Marilyn

    We try to go every year. We started doing that when our daughter was 2. We have usually gone in the heat of the summer because our son is older and it’s much harder to take him out of school without it affecting his grades. I highly suggest staying in a Disney resort because then you just hop on a bus and go back to your resort to rest for a few hours during the middle of the day before the kids get worn out. Then, just hop back on a bus to go back later. I have stayed off site twice (the one time we went way before my daughter was born and then one January for her 5th birthday). It’s just not the same. We like being immersed in it. I definitely recommend bringing a stroller for kids under 5 if you’re going in the summer (probably 4 and under any other time). And you’re so right… we did one very long vacation once (thinking it would probably be our ONLY WDW trip), I think it was 13 days, and we still did not get to do everything. We’ve been 10 times, I think (once to Disneyland) and we STILL have not done everything. There is just no way to do it all AND enjoy your trip. My husband is a Disney travel agent on the side. I suggest using a good one because if they’re like him, he actually does a lot of research and tells you what parks should be least crowded for each days, helps you make fast pass reservations, etc. We’ve never had an issue with the kids acting up on our trips. The kids we see acting up are acting up because they’ve gotten too hot and tired but the adults insist on staying in the park. Let them rest. They are kids.


      Wow, thank you! It is so helpful to hear from a Disney expert. Yeah, when the girls get older we are going to stay on site for sure. Which resort is your favorite?

  3. Rachel A. Hanson

    How fun!! We went to Disney World in May 2013 (pre-kid) and had a blast. The thing that I’d say made the heat bearable were the mid-day rain showers nearly every day, haha. And fast-passes are absolutely worth it!

  4. Pingback: In which I fish Wren out of a pool and other notable events from our vacation | Tales from the Mommy Trenches

  5. morgan

    WOW. I already saw the pictures on instagram and thought that you were pretty crazy πŸ˜‰ But yes, our experience also is that 1 adult per kid is a pretty good ratio. So happy you enjoyed your trip!
    Did you visit only one day?

    We’ve been to LEGOland this summer (blog post will follow, I still need to sift through the 277 pictures I took that day…) and we took a “bollerwagen” (a small handwagon. as far as my research went your most famous manufacturer is Radio Flyer) with us. This helped us a great deal in transporting all that stuff you carry around with kids in tow (food, drinks, diapers….) and you can throw a couple of toddlers inside if needed πŸ˜‰ Ours magically fit all three kids (ages 5, 4 and 2), even though its a very small one (its really old and we inherited it) compared to the ones you can buy nowadays. I’d prefer a handwagon to a stroller anytime πŸ™‚ Around here you can see lots of families dragging these through Zoos and parks and at our local zoo you can even borrow them πŸ™‚

    Getting to know the park beforehand is always a great idea, so you can steer around all the rides that definitely are not for the age group your kids are.

    as far as that selfiestick “problem”: in German parks they got forbidden on the rides (as well as taking any camera with you) because many people lost hold of their devices or hit poles outside the rides and people got hurt by these flying objects.

    1. sylcell Post author

      Yes, it was just for the day. We were sad, we could have happily been there all week! Aha, I didn’t think about the sticks being a nuisance on the rides! I’m sure that was the problem. A wagon is a great idea! Is it collapsible? Because the only thing at Disney is that you occasionally have to ride trains and trolleys with no room and we had to collapse the stroller and carry it on.

      1. morgan

        ours is made of wood, so definitely not collapsible (at least not in a reversible way πŸ˜€ ) I didn’t think of trains, d’oh. They didn’t have any trains or rides on LEGOland that didn’t kick you out at the same place where you entered it, so we just dumped it between all those strollers on the entry and hoped that no one would be interested in a handwagon that looked like it was about 100 years old πŸ˜‰
        I just looked up collapsible bollerwagen on amazon germany, seems like you can fold them to a size similar to a carry-on baggage.

      2. erica

        unfortunately wagons are not allowed in the disney parks. ive been many times growing up and ive taken both my kids. my son was 3 months his first trip, 2 yrs his second and 5 yrs this past trip which was my daughter’s first at 6 months old. i wore my daughter and brought a full size stroller so we could recline the seat when she fell asleep (did the same for my son’s first trip). staying on property is better because you can take a bus to any of the parks and go back around noon to the room for naps. ive only stayed in the value resorts (all stars movie, sports, music and pop century) pop century is my personal favorite but ive seen better reviews for art of animation with a family size such as yours (they have family suites) dining plan is good if you want to do a lot of sit down character meals. memory maker is also awesome. you can have any of the photographer cast members take family photos (in front of the castle or with characters) also you get ride photos and some photos called magic shots (in one my son was holding pascual from tangled and in another he was holding tinkerbell) theres a page on facebook that people share tips and ask questions on its called walt disney world tip, news and fun facts. also birnbaums unofficial guide to walt disney world is really helpful when youre planning. theres a new one each year so its up to date and theres even one for kids.


        Oh wow, you are a gold mine of Disney information! Thank you! I’ll check that stuff out!

  6. Amanda

    Sounds like it was a sucessful trip and that is what matters. Glad you didn’t have any breakdowns and looks like you had tons of helpers, which I am sure was great : )

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