Family Travel: Visiting DisneyWorld (with a toddler)


Curious what it’s like to visit DisneyWorld with two under three? We just spent a week exploring the resort parks in Orlando over the course of a five-day-hopper pass with Skyler (3 months), Hudson (almost 3 years), and my parents; Aron joined us most days after wrapping up at a conference. Here are some photos from our family vacation—along with some notes and tips I gleaned during our stay.

We arrived in Orlando after a relatively peaceful cross-country flight. And then, after what felt like 10 minutes of sleep, we started to sprint. Or at least that’s what we later agreed we were doing: it felt a bit like we sprinted… for five days straight. In other words, a lot of fun… a lot of sweat. And a sense of triumph.


My parents met us in Florida. We all stayed at a Wyndham timeshare property off-site, and they would come with the kids and I to the parks while Aron was in meetings. Sometimes, between the heat and the pace of the kids, I was worried we were going to kill them—but they were champs! I think (I hope) they really enjoyed it overall.

Each night, before heading off to the park, we’d call over to their room and make a vague plan for the day. My general feeling, with kids this young, is that you’re best off when you’ve planned just enough to keep everyone from standing around staring at a map when they’re hungry or tired, but not so much that you’re not willing to let it all go and just follow their lead.

Still, I learned that some planning is essential—especially in the era of the FastPass. First off, there’s a relatively new system called FastPass+. I won’t go into detail, becuase others will do much better. But read all about it before you go and get the app on your phone once you get your park tickets.

But here’s the thing: I actually think the FastPass program can be a plus/minus at the toddler age. Obviously, you don’t want to spend time waiting in line with a two-year-old (HUGE plus); but they also add the element of schedule to your day (potential minus). We found that Hudson was super excited about everything he saw right when we got into the Magic Kingdom—the characters around Walt’s statue, the double-decker bus making its way up Main Street, the figurines dancing in the shop window… and of course the beautiful steam train. What’s so nice about visiting with a two-year-old is that this is all enough for them. It’s sweet and wonderfully freeing. And you can just say “Sure! We’ll watch her make that cotton candy for five minutes!” “Sure! Let’s start off with the steam train ride around the park!”

After all, it’s good to remember, there’s a reason why kids under 3 are free!

So the only downside about a FastPass is that it’s likely to have you instead saying “No—we have to get all the way to Fantasyland (or wherever it may be) before our time slot expires. We’ll look later.” Also, if you haven’t figured it all out ahead of time, it will have you stopping at kiosks or looking at your phone a lot during the day. Personally, I was also little sad to have another reason to be looking at my phone in front of the kids. They already see us all staring down at them so much!

All this is just to say to plan accordingly. Decide ahead of time what kind of day you want to have and don’t let the time pressure of the FastPasses prevent you from slowing down. If you miss your slot, try to have an attitude of “oh well”: the really little kids won’t know. Once we figured this out, we learned to either keep postponing our times or just make them for a bit later in the day.


One other note on being flexible: I thought it was surprisingly hard to find good stopping places for nursing comfortably. Using a bottle was easiest, but then I worried about not pumping to compensate. And the baby center is great—but only if you happen to be nearby. So if you have a really little babe like we did, you’ll want to factor this in.

Most people aren’t crazy, though, and aren’t dragging a three-month-old along. So, just saying.

Hudson’s favorite things at the Magic Kingdom were probably the monorail and this Festival of Fantasy parade that featured a fire-breathing dragon. We watched it from the same spot on two separate days—before trying to distract him on a third rather than stand still in the scorching midday sun again.

It’s actually super sweet to watch him waving to characters and bouncing to the music. And it was wild seeing the crowd’s reaction to the Frozen princesses. They’ve achieved rock-star status! Parents were rushing toward the parade with cameras lifted in the air!

But here’s a tip: Don’t bother too much about getting spots before a parade. Unless it’s essential to you to sit down or have front-row views, you can usually stroll up just before one begins and find somewhere from which to stand and give little ones a lift. We at least found this to be true (on multiple occasions).


Another highlight for Hudson was Tom Sawyer’s Island. The crowds were thin and he could be in charge. He wanted to show us everything! Not so much the super-long, super-dark cave (geez! scary!), but everything else.


There are two Dumbos at DisneyWorld, and there’s an awesome playground inside the line where you can sit down, cool off, nurse the baby, and whatnot while they climb inside a mock circus tent. They give you these little restaurant-style buzzers to let you know when to rejoin the line. We had used a FastPass to skip the line, so we actually got in line again, just for this. We took the buzzer, and then returned it when we were done without finishing the wait for a second elephant ride.


I was pretty excited about Epcot—I’d looked forward to returning as an adult and sampling specialty foods and drinks around the World Showcase. But I have to admit I thought it was fairly boring for the toddler set. Lots of wide-open swaths of concrete and high-minded games.

The best attraction was Soarin’—something I’d been on once before at DisneyLand’s California Adventure park and loved then, too. You have to be 40″ and Hudson just made the cut. I was worried the sense of flying could scare him, but he was pretty fearless when it came to rides. (I understand that fears don’t always work linearly, however, and could still change.)

But here’s a perfect example of why managed expectations are key with kids this age at DisneyWorld: Hudson was growing tired and a little whiny and said “I want to ride THAT ride!” We thought he meant Soarin’, which was where we were headed and hoping he’d be tall enough to ride. (And which he loved.) But nope. He meant the escalator.


So we grabbed some sushi in Japan, a beer in Germany, and Hudson fell asleep around France.

Which brings me to: bring a comfortable stroller. You can rent strollers, but the double options at DisneyWorld looked pretty hard to nap in. We were lucky that Bumbleride sent us this awesome double stroller (the Indie Twin) for the trip. Though we rarely use a stroller with Hudson at home, we found he grew tired of walking within minutes of arriving. We were so glad we had a comfortable spot for both kids—especially when they both slept in it!

There’s stroller parking everywhere (check this out) and we never felt worried about someone stealing ours. (That said, it was helpful to have valuables in a single bag we could grab when parking it.) The only place where the double felt too tight was the tram—where you have to fold it up to ride in a narrow bench. Most days, one person (often my dad) would walk to the gates with the stroller while I rode the tram with the kids. On a couple of occasions, at the Magic Kingdom, he actually dropped us at the monorail stop and then parked—meeting us later.


There are many (many) character meals that take place in the parks and in the surrounding hotels. Some of them book up months in advance, especially (I’m told) those with princesses. Aron called the day before the trip to see if there were any dinners available at reasonable times and we got a table at Garden Grove, in the Swan Hotel. The prices weren’t too bad for a dinner out, and the characters were ones Hudson would know (Pluto and Goofy). Apparently, this one was not very popular—we were practically the only ones there! It made it a little too quiet, but Hudson had lots of chances to hug, observe, and have awkwardly one-sided conversations with the miming characters. (It’s so strange how they don’t talk!)

But it was still quite sweet: Hudson kept introducing his doggy to them, and talking about his real doggy—a black one—back home.


Only my parents visited the Hollywood Park, so I can’t say how it compares, but I really loved the Animal Park. We started a day there with a safari in their version of Kilimanjaro—it was a little like the Jungle Book Ride comes to life—and I thought the vistas across the large animal enclosures were pretty awesome. (By the way, if you’re planning on going without a FastPass, this is a good one to get to early.)

Other highlights included the new Expedition Everest and the Kali River Rapids. Hudson couldn’t go on Everest (it was like a scarier version of the Matterhorn at Disneyland), so my parents stayed off with him and Skyler while Aron and I took a turn. It was such a fun ride—with all kinds of thrilling surprises! Everyone actually clapped at the end.



Part of what made the Animal Park so great was the novelty (we’d never been there). But I also appreciated how many non-ride attractions it held.

My dad and I took the kids one morning and we spent nearly the entire time simply walking through shaded animal enclosures.


It grew hotter each day of the week. We always intended to go back to the resort for midday swims and naps, but found that getting to and from the parks could actually take a good deal of time. And with wanting to keep the kids’ bedtimes reasonable, it was often easier to brave the afternoon sun and have naps at the park. (Even if it was painful to leave just as the setting sun made it so comfortable!)

We learned that ample snacks, partially frozen water bottles, and frequent visits to the Casey Jr. splash zone made all the difference.

Much of those hot, packed days is already a blur. But one of my favorite parts of the trip was meeting Mickey Mouse. On a whim, we decided to get an afternoon FastPass for meeting Mickey at the Main Street Theatre. It reminded me of meeting Santa at Macy’s: you are ushered “backstage” and through a stage door for a private meeting with Mr. Mouse, and I’m guessing that there are a few doors being used at any one time. Still, the illusion is terrific—especially because the new Mickey Mouse talks! Aron said there are a few phrases pre-recorded, but you wouldn’t know it. He asked Hudson if he wanted to do the “Hot Dog dance” from the clubhouse cartoon with him, and we’re still talking about it!

There are plenty of reasons to wait until your kids are older—and asking—to go to DisneyWorld. And I think we were probably a bit overly ambitious to use the five-day-pass with these two (three days would have been ample). But there was an innocence to Hudson’s reactions that I’ve really enjoyed. It can indeed feel a bit magical—with the right expectations.

Quick note on the flights: It was Skyler’s first, and she was such a dreamy little lap infant on the way over (a bit less so on the way back, when we flew at night). Hudson had his own seat and we used the Cares Safety Restraint (an FAA-approved seatbelt for kids who could otherwise sit in a carseat). We love it: it keeps him seated and gives us peace of mind.

We do miss the carseat, however, because he fell asleep in it more easily! But it pushes him so far forward that it’s almost impossible for him not to kick the seatback ahead of him when he’s in it. It was our first taste of having two stretched across our laps. Has anyone had luck with a certain brand of neck-pillow for kids?

Finally: You may have also seen my venting on Twitter about United seating Hudson by himself twice (both times booting me and Skyler from my Economy Plus seat, switching Aron’s, and leaving Hudson stranded), but can’t help but mention it here, too. We had to rely on the kindness of strangers to switch, which luckily wasn’t a problem, but I hear about this happening all the time and it really shouldn’t be a passenger’s duty to ensure a two-year-old isn’t seated alone. We joked that—if wouldn’t have traumatized him—we could show him the call button!

For everyone’s sake, we resisted.

And despite that hiccup, we were left with happy memories of a busy week.

P.S. Disneyland with an 18-month-old; tips for flying with a baby or toddler, and packing for travel with kids.

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Let’s Discuss

  1. Oh Ashley, thanks for such a thorough and honest post. Your comments about Hudson’s excitement at meeting Mickey and riding the escalators made me laugh. My son is a bit younger than yours and we constantly take him to kid’s events hoping he’ll enjoy them and instead he gets a thrill out of mundane things like ice in his cup.

  2. Jessie

    I always enjoy your travel posts, I’m an anxious traveler & I am inspired by (& have admiration for) the way your family travels. We had the same experience with United when we flew to Maui last month. Thank goodness for the kindness of strangers! We talked to the agent at the gate before boarding & she said that there was nothing she could do, that we had to rely on the kindness of other passengers to switch with us! Economy Plus was a blessing on the red-eye flight home; we had the entire middle row to ourselves so my toddler son could stretch out & actually slept for a few hours.
    Sorry for such a long comment! Looking forward to more of your travelogues!

    • Ashley

      That’s so nice to hear! Thank you! I think it was good to have Aron’s work conference give us the nudge to do a big trip with Skyler right away.

  3. Motylek 82

    Thanks for sharing Ashley. Around same time you guys were in Florida, we took our girl to Paris and Disneyland. Plenty of people said she is too small, what a mistake. She just took it all in, reactions were pure, hardly any scares and hesitation. We truly believe, she really, really enjoyed 2days we spent there. And of course she is on and on about meeting Mickey and Minnie. Not to mention that she already knows all her Princesses names! Since our Princess turned 3 already, soon it’s Hudsons turn. Any ideas for the party?
    Greetings from Dublin

    • Ashley

      It’s of course a lot of money to visit these parks, so I understand holding off, but we really did have a nice time even as most will only be remembered by him via the pictures. As for a birthday: Not yet–it’s coming up so soon! Did you celebrate with a princess party?

      • Motylek82

        Exactly pictures are a key! But I bet he will never forget hugging Pluto or Goofy. Memories last forever.
        We went for Ben and Holly theme (British cartoon about Elves and Fairies), ahead of us are many years years of celebrating with Princesses, so we decided to hold off for one more year. But they were main theme if it comes to gifts. It was a challenge to undress her from her Ariel Mermaid dress in the middle of the night. Joys of parenthood I guess! lol
        As long as she had a wonderful day that’s all that matters!

  4. Vickie

    Looks like a great time was had by all, young and more mature!
    Can’t wait to see your itinerary for Italy, we are planning to revisit
    the Amalfi Coast and Umbria region next year.

    • Ashley

      I can’t believe how behind I still am on planning! But of course planning is half the fun, right? Will definitely share once we have it!

  5. This was so fun to read! Wonderful pictures. I have fond memories of visiting Disney World with my parents 3 times as a kid (ages 5, 6, and 11), and if I have kids of my own someday, I can’t wait to take them too. All the little details really are magical- like those mouse ears in Hudson’s ice cream cone. I remember loving the monorail and all the water rides, and I guess because I was a little older, Epcot.

  6. Ashley, I know you mostly kept to the theme parks, but next time you’re in Orlando you must spend at least part of a day in Winter Park. It’s about 20 minutes north of the parks and it’s the most charming little town (I grew up there)–great restaurants and shops and parks full of leafy oaks, plus it’s where the lovely Rifle Paper Co. is headquartered! xox

    • Ashley

      I would have loved to! A friend who’s from Orlando said the same thing and emailed us with a bunch of suggestions for restaurants in Winter Park. I thought we might make it over there some day, but I couldn’t believe how much I just wanted to get back to the hotel after a day at the parks. Next time, for sure!

  7. Kelly T.

    Great post!!! We have a 5 & 8 yo who are traveling pros. I believe it’s never too early to start! My son was 14 months when he did a 13 hour day at Disneykand & we had a great day!
    FYI: after making your flight reservations, call the airline and have the attendant “link” all of your reservations together. No one’s seats will change individually then. We learned this in April after having a JFK to Detroit leg get cancelled & us all get automatically rescheduled in different flights. Ugh.

    • Ashley

      Different flights?! Ugh indeed! See Aron’s reply below regarding linking. I swear we did everything by the book! So frustrating.

  8. Aron

    Good tip, Kelly! And your experience sounds awful!

    Sadly, I had done that, and that has worked in the past. Our seats were all together when I checked in the night before–it was only when we reprinted the boarding passes at the airport that the seat assignments were changed. And from economy plus to economy. The gate agent informed me that, “You must have done something wrong.” The customer service agent on the phone referred me to their contract of carriage which states that United reserves the right to re-asign any seat, at any time, for any reason. I was hoping for something like, “I see that we have split your family apart, that must be frustrating — let me see what I can do…”
    Sorry to rant, but United would do well to invest in some basic customer service communications skills.

    • Motylek82

      About two years ago when we flew to Maldives, Etihad upgraded our one year old Daughter to First Class to accommodate some other family. God only knows how they did it, since she wasn’t suppose to have her own seat! But there we are on the airport getting boarding passes for her, access to VIP lounge. So funny! Of course they let us tag along, pretty sweet deal!. Two seats in economy and 1 in first class worked out great. Still it’s a big mystery how they managed to do that and look on First Class passengers face when I walked in with toddler – priceless. Hope you guys will get more of this sort of surprises!

          • Motylek 82

            Indeed one of the most amazing holidays we had so far. We were fortunate to honeymoon over there and decided to take advantage of free flights for up to 2 year old’s and we flew once more. Many people were shocked how dare we to take small kiddo to such a romantic destination! lol We had the most amazing time ever! Pure bliss is the word that describes it. Take care guys and I wish you some amazing upgrade for flight to Italy! Have fun planning x

  9. Josephine

    Hi Ashley, I really enjoy reading your travel post. I have a 5 months old and planning to take our first flying trip next month. Just wondering if you would have any tips and travel essentials for baby in your future post? Thank you.

  10. Isn’t Expediton Everest so fun!?!? :-) Best Disney ride, in my opinion.
    The pic of Hudson with Goofy, and the last one where he looks like he is skipping… They just embody Disney Magic for me. Love this post so much and can’t wait to take my little guy on his first Disney trip. He’s just turned 13 months and we are in San Diego so I suspect it will be later this year sometime. I just can’t resist much longer! :-)


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