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WALT DISNEY WORLD DREAM VACATION PLANNING TIPS Mamahood | Disney Trips

We returned a few days ago from a week in Disney with our 2 older kids.  I had spent the better part of the last year planning for this trip and suddenly it’s over!!  Where do I even begin? Honestly, it is SO hard to put anything about this trip into words for me.  I AM a cheesy and emotional person, so that my kid’s first experience in Disney World makes me emotional isn’t really a surprise.  But I AM surprised that regardless of how exhausted I was there, and how much my feet hurt, I STILL end up in tears whenever I look at any of the thousands of pictures I have from our trip… but I think it’s because honestly?  I have been dreaming about bringing my kids to Disney World for over half my life.  I went as a child (and don’t have a lot of memories from that trip), and then again at 15…and 18…and 22.  It was during those 3 trips that my  adoration of Disney World, the pageantry, and the magic was completely solidified.  But seeing it though my kids eyes was a WHOLE other level, even with the complaining of tired and heat and feet hurt and hungry, over and over again (and then repeat).  They won’t remember any of that…but I do truly believe they will remember the magic they experienced there.

Planning a Disney trip is a HUGE job if you plan it fully (which I think is how you get the most out of it these days…it isn’t at all what it was when I was 6 or 15 or 18 or 22, I’ll tell you that!), and no one can pretend to know much about it after 1 trip with kids– I certainly do not.  But our first full day wasn’t very pleasant, and the rest were– so I feel like I can definitely share what worked really well for us vs what didn’t, and if you are planning a trip with your kids (or without!) in the future, maybe this can help you plan!  We definitely went over board and made this a total dream trip for our kids, both because it was their “YES!” trip celebrating a year of more “Not right nows” with a new baby, and party because we figured if we were going to spend 3 times what we typically do for a family vacation we might as well go all out!  I cannot wait to do it again with our 3rd baby in a few more years!

1). In my personal opinion and experience, you do want to do all the planning.  I went so far as to honestly plan our path through the parks each day based on our fast passes (will explain those soon!) and I’m not sure that much planning was needed- we definitely deviated a LOT which we expected… because…kids!  But I have friends who have tried to “wing it” with last minute plans and honestly, Disney just does not function like that well anymore unless you are good with standing in LOTS of long lines and honestly have no particular wants or wishes for the trip.  Knowing that we wanted our kids to experience a lot of the magic of BOTH meeting characters and experiencing rides (because they are HUGE for their ages and could ride almost everything), we made a lot of plans.  Disney Resorts and tickets book 6 months out, dining books 180 days out, and fast passes book 60 days out for those staying on property– and I recommend doing all of those as close to that time as possible if you have specific things you want!  I HIGHLY recommend along with this that you hire a planner! Disney travel agents are free for you and get their payment from Disney, and can make it all so easy.  We used Tressa from Me and the Mouse Travel at the recommendation of many friends, and adored her!

2). I DEFINITELY recommend staying on property if you have young kids, at least for your first trip. I totally understand that it’s more expensive than staying off and the benefits might not sound like they are worth the money. Your off site hotel might have food, or transportation, or even early or late magic hours included.  I just think staying on property is a part of the magic!  EVERYTHING is thought of and considered in terms of comfort for you and your kids, and that is so wroth it to me.  We stayed at Port Orleans Riverside in their Royal Rooms (themed like Princess Tiana’s bedroom)– and it was magnificent.  The children loved the room (there are headboards with nightlight fireworks) and it was just great. Clean, well kept, comfortable…it was wonderful and perfect for our kids ages. There are much more “kid-y” resorts (like Art of Animation) and much less also.  I just highly recommend staying on property!

3). You need a stroller. Unless your kids are maybe all 8 and above, or you are all about baby carriers in the heat (which I am not!), you just do.  It is so much walking.   Unfortunately you of course cannot take them into liens and that was where my kids struggled the first day- their feet were still super tired. But pretty much every time they could ride, they did, even at 4 and almost 7.  You can rent them there (we rented the City Mini Double from Kingdom Strollers and it was so easy).  Yes, they are a pain on the busses to and back from the resort, and a pain to navigate around…but 50% of the other people have them there too, and it just is a must have if you have kids unless you have another way to carry them.  Have a bag, or something on the handle that will help you find it at the rides- there are a LOT of strollers, many that look the same, and they get moved around while you are in rides by Disney cast members!  We used a big bag on the back because when you collapse for the bus or clear it out for security, it is a pain if you just have a ton of stuff in the bottom!

4). Know your kids personalities, and plan for them.  Our first full day, that was long and hot and lots of waiting we didn’t prepare for, didn’t totally take our specific kids into account because you just can’t always know ahead of time how they will do.  It was so important to us not to rush them around from place to place and to let them do what they wanted when they saw something as a part of their “yes” trip and we tried that the first day, but it just got out of hand with long waits (much longer than the app said!) very quickly.  But I think our enormous success the rest of the trip was because we planned well for their personalities.  We knew they would need little wait times- so even if there was a ride we knew they would love, if we didn’t have a fast pass for it and it said longer than 20 minutes, we didn’t do it.  We knew they would love characters but only in quieter settings vs meeting at parades or dance parties because they are shy- so we planned lots of meals and meet and greets.  We knew they would need a long, cool afternoon break (but didn’t want to take 3 hours our of our days to go back to the resort) so we had a long shady ice cream break every afternoon and planned some down time with “open play” at each place vs just lines and rides.  And don’t ever underestimate the magic of everything in a setting like that to kids– truly, our (very sweet and innocent) kid’s favorite rides were the ones you might assume are totally boring…It’s a Small World, Living with the Land, etc…our slightly shy and hesitant kids needed quiet rides with no suspense every few rides to calm down and relax.  Once we figured out the sort of mix of activities they needed, it was smooth sailing!

5). You don’t need many “extras”. This was our kids first flights (well, E1 went on one at 3 months but that hardly counts) and first big trip in that way– and we went all Disney out!  I’m always a little “extra” so I couldn’t help it…but we had little dollar store gifts for each morning outside the door from the characters, and Disney themed EVERYTHING on the trip and on and on…anything I could dream of to make it extra magical, I did.  And they loved it all– but they would have loved it all anyways!!!   So pick a few things that are important to you, and don’t worry about the rest!

What if you can’t afford a Disney trip? My friend….our kids PROBABLY loved splashing in the colorful resort fountain and swimming in the resort pool as much as anything else.  So while it’s amazing and I DO think they will remember it– it is our job as parents to make anything fun, and your kids don’t need a Disney trip to be happy! 🙂 No worries!  But if you can? I highly recommend it!  I am also going to share about how we decided to go now and what I recommend about ages, about the Bibbidi Bobbidi Boutique experience, about fast pass planning, about what we did for food, and about our Character Meals in the future.  Is there anything else specific you want to know about?? Let me know in the comments!

Here is just a SMALL smattering of some favorite pictures (mostly by me but a few by photo pass photographers)– there are so many more!

PS speaking of photo pass, here’s a bonus tip: Get the Memory Maker (this is a package where you pay a set amount and get access and downloads to EVERY picture you stop for on your trip!)! Even as a photographer, I felt it was SO worth it! And if you don’t mind a stranger having access to your pictures, you can split it with other people traveling when you are (find some Disney facebook groups and ask about this)!  We happened to have 3 friends all going within a few weeks and split with them but you can find others on facebook and split the cost many ways!  The Disney photographers can use your camera to take a family shot but it’s just so much easier to get the pass, stop for all the photos you want, and enjoy!

Click here to read all about our character meals and eating at Disney World!

Click here to read thoughts on the best time to bring your kids to Disney World!

Click here to read all about my top tips for bringing your DSLR camera to Disney World!

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  1. Absolutely wonderful! I’m so happy your family had a blast! I would love to hear about what Character meals you did! We are going in May and trying to figure that out! And what little “Extras” you did each day? You mentioned little gifts! I was thinking about doing something similar but would love to hear your ideas! Thanks!

    • Jill says:

      Hey Lauren!! I will share the food/character meals blog post next then!!
      In terms of extras: so we had little gifts every day (3 days were little things they could play with in line- sticker book type things, 1 was a pressed pennies book and we did lots of pressed pennies there, and 1 was glow wands for a late night– I wrote them notes from the different characters and signed them with their “signatures” from pictures online! I put them outside the door in the AM, and let them find them. It WAS super fun– but they were so happy anyways they probably didn’t need it haha. I think you can have Mickey do a wake up call for them there (ask your resort about that if you are staying on site but I don’t think you are right?). And then in terms of all the other extra…we just had so many themed things for them…mickey ears/hat, mickey and minnie blankets for cold late nights at the park (but it was 10 degrees warmer than usual when we were there), shirts, fun lights for the stroller at night, etc. It was all SO fun– but kids will love WHATEVER it is and looks like!

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I'm Jill, a wedding and portrait photographer based out of Chicago and Central Illinois, and available world wide! I'm also a photography educator, wife to my favorite person on the planet, mama to 3 amazing kids and an energetic Aussie, and obsessed with statement jewelry and all desserts (especially fruit pies!). 

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