[00:00:00] Dana Stanley: Have you ever hit confirm on a Disney trip and then immediately thought, wait, what did I just do? Because that was me this week. We weren’t even sure if we were going to get down to Disney World at all, and then boom, we’re booked for next month and not just at any resort, but one that we’ve never stayed at before.

[00:00:18] Dana Stanley: In this episode, I’m walking you through the exact steps I’m taking to prep for this last minute Disney trip. From what I’m skipping completely to how I’m reworking my list of must dos. To what planning looks like when you still want the trip to feel intentional, but you also only have less than 30 days to plan everything.

[00:00:38] Dana Stanley: We’re gonna be talking about summer crowds, skyliner strategy, and the balancing act of me on vacation with my kids, and also working on content for my business, which includes the podcast that you’re listening to right now. So if you’ve ever wondered how I actually plan my own Disney trips. Or you found yourself tempted by maybe booking a last minute deal and aren’t sure if you can pull it off in time.

[00:01:01] Dana Stanley: This episode is for you. Hello and welcome to the Laid Back Magic Way podcast. I’m your host, Dana Stanley, creator of Laid Back Magic. As a mom of three, I know how tough it can be to find time to plan a Disney World trip. That doesn’t leave you feeling stressed or overwhelmed. That’s why I’m here to help moms like you create Disney vacations that feel even better than they look on paper here.

[00:01:24] Dana Stanley: We’re not chasing perfection, but creating our next favorite memories. So whether you’re brand new to Disney or looking to go deeper into the details, this podcast is your go-to for simple tips, mindset shifts, real life trip recaps, and expert insights to make your trip magical and manageable. New episodes drop every Monday.

[00:01:42] Dana Stanley: So be sure to subscribe so you never miss a moment. Okay, let’s dive in. We are officially booked for Disney World, and after putting off for months, waiting for the perfect resort with the perfect dates, it ended up being a really last minute trip for next month. There were just so many things that we were working around, especially with like a busy summer and finally pulled the trigger when there was a one bedroom available at Riviera for the perfect dates that I wanted.

[00:02:10] Dana Stanley: I really wanted a resort that was new to us for this trip. You guys know I’m a Boardwalk fan, but after our last trip, I was really craving something just different. Even if it wasn’t my favorite or perfect, I was really just craving something different and kind of like something to remember each trip by different things.

[00:02:34] Dana Stanley: I feel like when you stay at the same resort over and over, all the trips can kind of start to run together. Whereas you can like reference like the time that we stayed at the Poly or the boardwalk, things like that. So the Riviera just made sense. Now that we have three kids, we can definitely still do a studio.

[00:02:49] Dana Stanley: But a one bedroom is always really nice. I wish I could say that this was my first, last minute trip that’s like under 60 days, but this has been kind of the normal thing with the exception of when we visit with our extended family that we plan. Many, many months in advance. But when it’s just the five of us, it ends up being just like when the stars align, if we can get like a room or rental between flights and our schedules.

[00:03:17] Dana Stanley: So I wanna chat about what I’m doing for this trip in particular, some things I would do on every trip anyway, but specifically when it comes to last minute trips like this. But first, here’s what I’m not doing. I’m not booking anything right away. Like I’m not rushing to rent a stroller and book dining reservations and like order clothes.

[00:03:38] Dana Stanley: I am not rushing to do anything because I know that there are certain things that have to happen first, and it doesn’t matter if I’m planning a year out or a month out, and I’m not stressing about the fact that I missed my dining day. This is something that used to stress me out and I put a lot of emphasis.

[00:03:58] Dana Stanley: On the day that my dining reservations opened. So if you don’t already know for table service, sit down restaurants and Disney World, you’ll need a reservation. And those open up 60 days at 6:00 AM And normally I would be up ready to go with my dining reservations in order of priorities, you know, very strategic and I’d have backups and all of those things.

[00:04:22] Dana Stanley: And I know the instinct when you’re feeling behind is to like immediately go into the app and hop into dining reservations and start booking for places that maybe are hard to get and you feel behind and you think that there’s gonna be nothing left. But I’ve learned the hard way that booking anything before I really know what parks I’ll be in and when is kind of just like a recipe for disaster getting ahead of yourself.

[00:04:48] Dana Stanley: So the first thing I did after I hit book was actually print out two things from my own planning course, laid back Magic, my intention journal and my checklist. And the checklist actually felt good because it’s something that’s normally maybe over six months, and I was just able to like check, check, check.

[00:05:05] Dana Stanley: Like I did all of these things, but I just wanna make sure that I’m not missing anything because the planning timeline is so condensed now. The journal is wonderful for any trip, and you can actually grab that for free at lead back magic way.com/journal. I’ll leave a link for you in the show notes, but I really wanted to fill this out right away because even though I’ve made it my job around Disney World, we don’t go often enough that I could just skip this step.

[00:05:32] Dana Stanley: We’re not going every week. We’re not local. We’re not even going every month. So it’s still very special when we get to go. And I feel like, I dunno if it’s my age or because I’m done having more kids, I’m like more nostalgic than ever about actually getting to be in Disney with my kids while they’re little.

[00:05:50] Dana Stanley: And I love Disney World obviously, so I want to do everything and all the new things that we haven’t seen and there’s a lot of new stuff. This trip I’ve been keeping, like a general Google doc of things I want to hit on our next trip. And when I looked at it recently, it was like 16 things and that is not gonna happen.

[00:06:08] Dana Stanley: This is a five day trip. 16 new things I know are not gonna work. So filling out this journal reminded me that yes, I do need to bring back some content for work, but I can also prioritize what we want to do first, and then I’ll work backwards from there and making content around things that I already know we want to do, not the other way around.

[00:06:31] Dana Stanley: I started eliminating that list pretty quickly. Once I talk to the kids, and this is the next thing that I did right away, because one of the downsides of being so last minute, or having less time to plan is that there isn’t as long of like a hype period for the kids. Sometimes you book something, you know, a year, maybe a little less away, and the kids are pumped that entire time.

[00:06:53] Dana Stanley: I could also see this having its downsides too, depending on how you look at it. But in our case, I told the girls immediately, like within 10 minutes of the room being booked, I. This isn’t always on the list. I’m not usually like in a rush to tell them, but it’s actually making a huge difference on this trip in particular because it’s surprising, like what your kids will say, what they don’t care about specifically, and that’s making it really easy for me to just cross things off the list.

[00:07:23] Dana Stanley: I feel like sometimes you get a lot of information from them by like the questions that they ask you too. When I told them that we were going to Disney and I said we were staying at a new resort. My daughter immediately said, oh, is it the one with the Moana pool? And I know she saw that from watching videos of the Poly Tower when it opened.

[00:07:43] Dana Stanley: So that was like a good thing to kind of just get ahead of, of like, Hey, no, we are not going there. There is no, you know, Moana pool. But, and then I could tell her of like all the exciting things about the Riviera that I think she will like, if you haven’t been to Disney World yet and your kids. Don’t know what to expect.

[00:08:02] Dana Stanley: That actually makes it a lot easier because they don’t really have. Expectations or know what to expect at all. But I would watch some YouTube videos with them ahead of time and see what kind of pops up. Maybe do like a walkthrough and then see what they say or what they ask about, and then you could show them like very specific character meals or pools and see what kind of makes them glaze over or what makes them excited.

[00:08:27] Dana Stanley: On our last trip to the Boardwalk, it was during the media previews of the new Cake Bake Shop. So the girl saw the outside with all the lights and the menus, and it’s very pretty. So they happened to be very interested in eating there, but they had never seen the inside. So I went on YouTube and I put in cake bake shop reviews and things like that so that the girls could see the insides.

[00:08:51] Dana Stanley: Because I don’t know how my girls feel sometimes about things that are like very girly. They can go either way. It’s a very like feminine, little bit more fancy upscale place feeling like everything has glitter on it. And I was surprised they were both completely into it. They’re pumped about the cake and I’m pumped about the peanut butter mousse pie that’s on my list.

[00:09:13] Dana Stanley: So that was like a good thing to just. Bring up because otherwise I don’t know if I would’ve known that they were into that or cared about that, and I might’ve taken it off the list. I feel like watching any videos and like resort walkthroughs are very low effort ways to help your kids feel excited and also set the expectations ahead of time so they’re not like surprised by anything.

[00:09:39] Dana Stanley: This was the type of trip where I had the perfect chance to make it a surprise. Like the girls didn’t know. It was kind of just like out of the blue. And I had done that in the past with my oldest, where we woke her up. And put her in the car for school and we drove to the airport instead and it was very fun, but I realized that it like wasn’t for me.

[00:10:00] Dana Stanley: I feel like it’s more fun for them to like know that we’re going. That’s just how I felt. It was almost like when you build something up of like, this is gonna be this epic surprise and then they just have so many questions and they need time to like process it. And I remember coming home and saying to my husband, I don’t think I wanna do a surprise to Disney again.

[00:10:21] Dana Stanley: Like, I’m glad we did it and it was really fun, but it feels more fun to me. Not surprising them. Maybe I could like tell them in a fun way, but not the waking up and going to Disney type surprise, if that makes sense. I thought about it though I did. I mentioned that this resort is new to me, and again, that’s the Riviera.

[00:10:42] Dana Stanley: I think of this as like boardwalk’s neighbor, but the downside for me is that there’s nowhere walkable outside of Caribbean beach next door because of this. Once I had my resort reservation linked to my account and everything was ready to go, I started looking at the map of this resort to get familiar.

[00:11:02] Dana Stanley: I had already looked and seen the floor plan before we booked, obviously, but there were a lot of variables, especially because it’s somewhere I haven’t been. And the biggest thing is the Skyliner station. I have never stayed at a resort that is on the Skyliner route, which means for Hollywood Studios and Epcot, I will not be able to walk, which is going to be kind of a shocker to me ’cause I’m just used to being able to walk.

[00:11:26] Dana Stanley: And there’s also no buses to those parks. You have to take the skyliner. I visited the Riviera before and used the Skyliner to get there, but I have not depended on it so much for getting to and from Epcot in Hollywood studios. And that story takes a little bit of a turn when I tell you that I am terrified of heights and the first and last time I took a ride on the Skyliner.

[00:11:51] Dana Stanley: I cried like a little girl. So it’s definitely something that’s been on my mind. I keep telling myself that I’m gonna be okay and I can suck it up, but I do want the whole experience of the Skyliner to be as stress free as possible. So the biggest thing I have to think about is that our double stroller is the Zoey twin, and it’s a side by side double, which means it’s going to have to get folded up for the skyliner.

[00:12:18] Dana Stanley: Single strollers and other doubles that are front and back can just be wheeled right on. So this is something I’m kind of going back and forth and thinking about it more than any other trip is considering if I actually maybe want to try to rent a different kind of stroller so we don’t have to collapse it, will I be taking the skyliner that much that it will be annoying having take the two kids out and collapse my double versus renting something else and we can just push it on?

[00:12:47] Dana Stanley: I. That’s why I know sketching out my trip is so, so important before I do anything and like really slow down because maybe we end up Ubering to different places more, or we’re going to Magic Kingdom more than we think. Maybe we’re not even going to Hollywood Studios, which I doubt, but there’s so many variables of making these big decisions.

[00:13:10] Dana Stanley: Jumping ahead and renting a stroller before thinking about it. That I really don’t wanna do anything until I have a bird’s eye view and know exactly what my tentative plans are, and that was the next immediate thing that I did was start sketching. I printed out my little sketch planner and started plugging in which parks were going to be more crowded on which days, and using crowd calendars that I trust, which is thrill data.

[00:13:33] Dana Stanley: An undercover tourist, you can literally see spikes and dips per park, not just across even Disney World as a whole. For example, Mondays at Magic Kingdom, I know to avoid the data says it, the ticket data says it. My own experience says it. So that’s something that I’m going to sketch so that I know that we’re not going to be a Magic Kingdom on Monday.

[00:13:54] Dana Stanley: Same thing. I know that Epcot. On like Friday, Saturday nights around the world, showcase feel really cramped and the lines for everything get really long. So I’m going to be avoiding that. There are better and worse times to go to Disney World throughout the year, and they’re all gonna have their pluses and minuses.

[00:14:10] Dana Stanley: I don’t think that anytime is a good time, and to be honest, when we’re going is like kind of my least favorite time because it’s a little bit more crowded and it’s very hot. But if you listen to my summer episode, and I’ll link that in the show notes for you if you haven’t. I do have some things that I won’t normally do during other trips that I’ll absolutely do during the summer to make it more manageable and like not the worst time of year when I know it’s gonna be on the busier side.

[00:14:38] Dana Stanley: I get very serious about the actual parks on which days a lot of people ask me, when’s the least crowded time to go to Disney? Or they avoid holidays altogether. Which I get and totally recommend, but don’t forget that the crowds can go up and down within the parks. Your trip can feel wildly different depending on what day you’re going where.

[00:15:00] Dana Stanley: That’s how I’ve been spending the last two or three mornings since this was booked, was sketch, sketch, sketch. Next I took inventory of just kind of like the things that I have on hand and like our gear, luggage, stroller, stroller, fans, things like that. This will be our eighth flight this year with the kids.

[00:15:18] Dana Stanley: So thankfully I have everything freshly unpacked from our last vacation, if that makes sense. I kinda like mentally know where everything is at the moment. I just did like a big closet clean out, which by the way, like a real summer closet clean out feels so good. I actually like cleaned my closet, like vacuumed it and sprayed it down.

[00:15:39] Dana Stanley: It felt so good. I made sure we were all good to go there. I don’t need to bring a ton of extras. I don’t need to order a bunch of mini toiletries and go hog wild with like ordering things because I’m pretty set there and I’m glad I took inventory right away because I think our like default is to just like go on Amazon and order a bunch of things and then when you start packing you’re like, oh, I have like two of these sunscreens, or, oh, I have two of these deodorants.

[00:16:06] Dana Stanley: So I always recommend like slowing down and actually. Compiling things that you have so you’re not double ordering things. The thing that I really need to decide in the next few days is if I’m renting a stroller or not. I wanna do this sooner than later. So definitely in my mind, we worst case have a stroller, but if I wanna rent one, I.

[00:16:25] Dana Stanley: I wanna get that done asap. And the last thing I did slash am doing, ’cause I haven’t actually done it yet, is to do any dining or set any dining alerts. This is going to be last and not first because you cannot make dining reservations. Or set alerts for dining reservations until you know where you’re going to be and when.

[00:16:48] Dana Stanley: I think sometimes we just assume, okay, I’m just gonna book these places. I know I wanna go, and then kind of work around that or grab whatever time you can. And then you’re like trying to put a square peg in a round hole. You’re like working backwards and trying to make something fit that maybe isn’t going to work around other things like the park day crowds.

[00:17:09] Dana Stanley: Or events or park hours, or you’re like working backwards and trying to make it work. And when your dining doesn’t match your park plans, it like throws everything off. And I’ve just learned that. So I’m waiting to do this last and I have pretty good confidence that I’m gonna get what I want anyway, so that’s where we are right now.

[00:17:29] Dana Stanley: The last minute trip is booked, the room, my plans are kind of sketched out. I’ve taken inventory of my gear. And I’ve set my intentions from the get go. And there’s still a lot I have to figure out here, like which park days are locked in, what I’ll prioritize for my content, obviously where we’re going to eat, but I’m doing this the way that I teach one step at a time, and especially in the right order.

[00:17:54] Dana Stanley: If you wanna steal my checklist or the journal I mentioned, I’ll link it in the show notes for you. And if you’re planning a last minute trip yourself, I hope this episode was useful. Let me know how it goes. I am right in the planning boat with you. You can always DM me on Instagram I’m at @somewhereworthwhile and I can’t wait to chat with you there.

[00:18:12] Dana Stanley: Thank you so much for joining me on this episode of the Laid Back Magic Way podcast. If you enjoyed today’s episode and it was helpful for you, it would mean the world to me if you’d write a quick review, your reviews, help more moms like you find the show, and I read every single one of them seriously.

[00:18:28] Dana Stanley: Thank you in advance. You can find me on Instagram. At somewhere worthwhile and I’d love to hear from you there. DM me if you have any questions about this episode or what you’d like to see in future ones. Until then, keep planning for your next favorite memory and I’ll see you next time.