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Jessie only had two park days, a family visit planned afterward, and an unexpected early park closure that could have completely changed her plans. But somehow, this ended up being one of those Disney trips that felt relaxed, flexible, and full of the moments that mattered most.
In this Disney trip report, Jessie joins me to break down exactly how she approached a short Walt Disney World vacation, from choosing the right resort and park ticket strategy to navigating Lightning Lanes, park hopping, and a few surprises along the way.
If you’ve ever wondered whether a shorter trip can still feel worthwhile, this episode is proof that you don’t need a full week at Disney to have an amazing experience.
In this episode, we cover:
From Skyliner strategy and park hopping to fireworks, parade viewing, and ride priorities, this Disney trip report is packed with practical takeaways for families trying to make the most of a shorter vacation.
And if you’re debating whether a Disney World park hopper is worth the extra cost, or whether Caribbean beach resort is the right fit for your family, Jessie shares exactly what worked, what surprised her, and why she never felt rushed despite having limited time.Come hang out with us over on Instagram @somewhereworthwhile and let us know: if you only had two park days, how would you spend them?
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Podcast music by Podington Bear, track: ‘Filaments’, licensed under CC BY-NC, courtesy of Free Music Archive.
[00:00:00] Dana: Hi, Jessie. Welcome to the Laid Back Magic Way podcast. I know you just got back from Disney World, I wanna say two days ago? When did you get back?
[00:00:12] Jessie: We got back Tuesday morning this past week. It feels like it’s been longer, but we flew back home out of Fort Lauderdale Tuesday morning and got to Albany around lunchtime. And yeah, we’ve been settling back in since
[00:00:28] Dana: I’m excited to talk about your trip because I know we were talking about it because you’re a Laid Back Magic member, so I had a general sense. I saw your original sketch, and then you were thrown a few curve balls. But you’ve been to Disney World before, so it wasn’t like your first time. I’m sure there’s first times for a lot of things, which we’re gonna talk about.
[00:00:49] Dana: But I wanted to ask you, going into it with like a blank slate, what did you know were like the non-negotiables that you definitely wanted to do?
[00:00:59] Jessie: We knew– I think I just knew realistically that this was a Disney trip tacked on to what would be later in the week a, a visit with family in South Florida. So I knew that, we could spay– spend maybe three nights but we had to limit our time. Time was definitely a constraint. I think I knew that I wanted our trip to be kinda ride-heavy.
[00:01:24] Jessie: We’re definitely fans of rides. We started out taking my son to the Magic Kingdom just for the day in the Genie\+ days, and would just hop from ride to ride and have a ton of fun and make a day of it split up- splitting off from visiting family in South Florida. So last year we finally tried our first overnight and then, we wanted to kinda make it even better this time around.
[00:01:50] Jessie: But I knew that I wanted our stay to be ride-heavy. And I know that my son is crazy about Disney pools and swimming, so I knew that we wanted a good bit of pool time in there. So I kinda planned it that our arrival day and our departure day we had a good bit of pool, good bit of pool time fit in
[00:02:13] Dana: Yeah. A six-year-old boy is definitely the perfect age for a lot of pool time and a lot of rides. So what kind of… Well, I’ll ask you this first. What resort did you stay at, and how did you land on that? ‘Cause I know the first time you went, I believe you stayed at Pop Century
[00:02:32] Jessie: That’s right, yeah. So when we went last year, we stayed at Pop Century, and that was great. We loved the Skyliner and everything. And my son totally loved the hippie-dippie pool. But I found that the line at the Skyliner at Pop, it took quite a while to process the morning we were trying to do early entry at Epcot last year, and I feel like we had a fail going to Remy’s.
[00:02:56] Jessie: Like, ended up in this huge line way back by Morocco,
[00:03:00] Dana: Oh, wow.
[00:03:01] Jessie: but didn’t really know… Yes. But didn’t really know what was more normal or not. So I had that in the back of my mind as I was planning this year, and I actually booked the trip with us staying at Pop again. But later I read an article about how Caribbean Beach can be h- a heads above Pop Century as far as the Skyliner goes, that there’s a, I think, a smaller number of peop- capacity, at Caribbean Beach Resort, plus folks kinda distribute themselves to either the Riviera stop if you’re on the northern end or
[00:03:43] Dana: Right.
[00:03:44] Jessie: the regular stop on the other end.
[00:03:46] Jessie: So
[00:03:46] Dana: Because if anyone’s listening and wondering what she’s talking about, there’s multiple resorts on the Skyliner route that will go to Epcot and Hollywood Studios, but they use Caribbean Beach as the hub. So you have to get off at Caribbean Beach and then go whatever direction.
[00:04:03] Dana: So it would, I would assume, already be dispersed, I think is what you’re saying. Like, by the time you’re at Caribbean Beach, there’s less people. So that being your starting point sounds better. So that’s pretty cool. I know I’ve been to Caribbean Beach because I really like Sebastian’s. Did you have a chance to eat there?
[00:04:23] Jessie: Yeah, we actually like thinking about the rhythm of the trip that I wanted and like trying to set an intention of, a thoughtful, like joyful trip together. I had planned it that we would go to Sebastian’s the night of our arrival. And that was great. My husband fell in love with it, and it was a little harder for my son.
[00:04:44] Jessie: He was, wanting to be on my phone and
[00:04:48] Dana: Oh, I
[00:04:49] Dana: know,
[00:04:50] Jessie: hadn’t transitioned into the magic or something
[00:04:53] Dana: I know. Travel.
[00:04:53] Jessie: had been a long travel day, right? , But no, the whole Sebastian’s Bistro experience was great, and it totally won my husband over. , I feel like he totally loved it, all the food and
[00:05:06] Dana: good to get the husband in a good mood just as much as the kid on the first day. Maybe even more so than the kid. ‘Cause travel days are hard even with the screen time too, because you were flying, so he probably was just, like, a zombie at that point. So I totally get it. But I remember when we ate there it was, you just have kind of the stars align and you have a really good night, so I have a happy memory of it.
[00:05:31] Dana: But my husband loved that it was, like, the cheapest meal of the trip, ’cause it was towards the end, and we got the bill and we were like, “Really? Is this right? This can’t be right.” So it’s very affordable. It’s easy to get a reservation. And it’s, it is, like, a night… And we did the same thing. We did it on the day of arrival, and it was just happy vibes.
[00:05:51] Dana: What did you think about Caribbean Beach overall as far as like, when you had to take the bus to Magic Kingdom? Did that all feel good?
[00:06:02] Jessie: It felt pretty good. So that was our, By that point, it was our second morning and our second bus experience because we had taken the bus home after Happily Ever After from Magic Kingdom the night before. So the bus the next morning felt pretty smooth. We were probably some of the only people waiting for the bus at our bus stop.
[00:06:24] Jessie: We had gotten a Little Mermaid room down in Trinidad, I guess. And
[00:06:29] Dana: a good building to be in
[00:06:32] Jessie: Yeah, we loved it. I had put in a request for it and we ended up getting it and, nice to have the new bathroom and the refresh room and all of that.
[00:06:41] Dana: Awesome
[00:06:42] Jessie: But yeah, the bus was relatively simple that morning. And the night before was our first bus experience.
[00:06:50] Jessie: I was bracing myself for like the bus after Happily Ever After and told my husband all about it and Was prepared to book a minivan if we needed, but it actually worked out fine
[00:07:05] Dana: It’s better to expe- I mean, you wanna have a positive attitude. I was thinking about this the other day. I was like, ’cause I’m a pessimist, I just am, or like Murphy’s Law. , Oh, it’s gonna be this, it’s gonna be that. So it’s like you don’t wanna be like that. You wanna have a positive attitude, but at the same time, like underneath of it, un- underneath of the positive attitude, be prepared that the worst could happen, and then you’ll be pleasantly surprised and happy when that doesn’t happen.
[00:07:35] Dana: Walk me through your tickets and the way that you structured the park, ’cause I know you didn’t go into the parks the day you got there, and then you had two-day park hoppers. What did that look like? How did you structure that out?
[00:07:49] Jessie: So I ended up realizing we could plan it with just two days of park hoppers just because of our limited time and trying to keep us at just three nights at the resort. I decided we really wanted to hit Magic Kingdom and Epcot and Hollywood Studios, and I felt like having two days of park hoppers was, how we could accomplish that. So I think I had booked those park hoppers from the start, and I think it felt like an indulgence when I booked them from the start. You pay a little more, than… I think there was even– There were all these deals that was at the beginning of 2026, like there might have been a three, three, four-park, four-night, kind of promo and a different like three-park, three-day maybe without Magic Kingdom promo.
[00:08:43] Jessie: So it felt a little like indulgent to book two days of park hoppers. But when I think, it was what worked best for our schedule, but also when I found out that Magic Kingdom was closing early
[00:08:56] Dana: Yes
[00:08:57] Jessie: The, our Magic Kingdom day, then that kind of– it was a relief to know that the park hoppers were really required to do what we had to do.
[00:09:07] Dana: Yeah, like you
[00:09:08] Jessie: What we wanted to do,
[00:09:10] Dana: especially because you wanted to do Phantasmic and Happily Ever After, I think
[00:09:17] Jessie: Yeah, we’d never done Fantasmic! before, and I’ve heard people say it has a few kind of scary or dark moments, but my son is totally into Halloween and scary stuff, so it sounded like it would be up our alley. So I wanted to do that. I knew it would probably be an easy Skyliner ride home. And Happily Ever After is funny.
[00:09:37] Jessie: I felt like we had to like, give it another chance or try it again. Like, I feel like we had seen it previously right before, a two-and-a-half-hour drive to see family. This was probably, our last trip or a long day trip. So I felt like we had to try it again. We definitely wanted to see Starlight, which ended up being awesome.
[00:10:02] Dana: Wait to see that. I’m excited about that
[00:10:04] Jessie: It was great. We had just– We had pretty much come over from Epcot and pretty much posted up between the confectionary and the theater, maybe the Town Square Theater where you meet Mickey. And we met another family there and we’re right by the curb, and my son was sharing like glow bracelets with-
[00:10:28] Dana: Oh, I love that
[00:10:29] Jessie: family. And yeah, that was one of those nice little Disney moments, but it was nice to have, him have some interaction and, some fun while we were waiting for the parade to start.
[00:10:40] Dana: kid problems, right? You’re like… disney’s a great place to be an only child, ’cause when we used to go before we had kids, we would just go with my niece, who’s an only child, and she loved it. She loved getting spoiled, and then you have all the kids that you can play with, but then you don’t have to, , share your food or your toys with, and be like, “See you later.”
[00:11:01] Dana: So I’m sure Jude was having a blast. That was one of the things that when I was looking at questions you posted in the community, was you had your original sketch, then you saw that Magic Kingdom was closing early on the, like the night that you thought to plan for the Starlight Parade and Happily Ever After, it closed at 5:30.
[00:11:23] Dana: And I think this is a great thing to talk about, because this is our future going into the August, September, October, November, December months, is Magic Kingdom closes, , over 60 times it closes early for the rest of the year. So I know everyone’s going to be having this thought of, “Oh, we’re gonna do this,” and then they’re gonna check the times and realizes that it closes early.
[00:11:49] Dana: And like you said, you felt indulgent with the Park Hopper, but it was a requirement to end up doing what you wanted to do anyway. So it was like a happy accident. But you were able to move things around and not get, , pigeonholed into your plans and be flexible. So you did Epcot the first day.
[00:12:12] Dana: So the first morning was Epcot, then hopped to Magic Kingdom. Did you take a break at all, or did you just take the monorail? What did you do?
[00:12:22] Jessie: We had a little bit of a break at Epcot. It was raining on and off, and we I think we went to Connections and got some food and kinda camped out there for a little bit while it was raining. I feel like they have a big, , bench seat where my son could just, , get with his new, , Coke can pillow from Club Cool and,
[00:12:43] Dana: Oh yeah, I know the benches you’re talking about. We end up there a lot too. Everybody does.
[00:12:48] Jessie: It was a good place for him to kinda relax and us to be out of the rain and, , rest up a little before, before moving on. But it helped to know that we could have gone back to the resort if we had to, but I knew we, we probably wouldn’t have to. And I had tried to plan our itinerary for the day geographically, , just kinda making one big figure eight or something around Epcot. And I thought we would have gone all the way back through World Showcase at the end, and I realized, oh, maybe we’ll walk to Beach Club and take the bus to Magic Kingdom. But it actually turned out that we used a lot of our time for rides.
[00:13:32] Dana: Mm-hmm.
[00:13:33] Jessie: I had gotten Test Track as a Lightning Lane, and since it was raining on and off, I lost it twice as a Lightning Lane.
[00:13:43] Jessie: And I feel like the last time that I– the last time that I traveled to Disney that when I had a Multi-Experience Pass, I thought that it showed up where my Lightning Lanes were. But this time around, that was showing up in the My Plans tab. So I hadn’t realized I could just use it right away. So we had been at Connections, it had been rainy, and we were about to get on the monorail to go to Magic Kingdom, and I saw two guest services people, and my husband was like, “Why don’t you just ask?”
[00:14:17] Jessie: I asked them and I found out, , oh, that was actually our Multi-Experience Pass. So at that point, we got to go do Test Track twice, and my son– None of us had ever done it and,
[00:14:29] Dana: Did he love it?
[00:14:31] Jessie: it. Yeah, he really did.
[00:14:33] Dana: That’s like the perfect ride for a three-person family too, ’cause it’s three seats across, which makes it so fun. And
[00:14:39] Jessie: We have some
[00:14:40] Dana: is just a good age for that
[00:14:42] Jessie: Yeah, we have some fun photos from it, and he has kinda long curly hair, and when you go outside, and really pick up speed, he was like, “My hair,” and it was all over his
[00:14:53] Dana: Could you even see his face? ‘Cause my daughter, it just goes right in front of her face. You don’t even see anything. I’m like, “You need like a hair band or something.”
[00:15:00] Jessie: Right. Yeah. Yeah, it was kinda like that. But he loved it, so the fact we got to just ride it twice in a row right then was pretty wonderful.
[00:15:09] Dana: That’s a happy mistake. Worked out. Yeah.
[00:15:12] Jessie: Yes
[00:15:13] Dana: So then I, we were talking about it before and I went on a tangent, but you were talking about how you wanted to give Happily Ever After a second chance it seems like. W- were you able… Did you stay where you were, where you watched the Starlight Parade, or did you move to watch Happily Ever After?
[00:15:33] Jessie: So we, we moved a little bit. We moved to the center of that circle in the middle of Town Square. And in the break between the end of the parade and the beginning of the fireworks, we changed my son into pajamas and, tried to be strategic about leaving the park relatively quickly after the fireworks were done. And I think I just chose that spot back in Town Square as a, easy exit kind of point. And the view
[00:16:04] Dana: far in the front
[00:16:05] Jessie: Right. Yeah. And the view was pretty good. , We could see, some of the fireworks down Main Street. I thought we would see more projections on Main Street. I don’t know if it was because the time of year and it’s so light out in the evening in May, but it seemed like a lot of the projections on Main Street were the, the half closer to the castle rather than back where we were.
[00:16:29] Dana: Okay
[00:16:30] Jessie: but yeah, it went pretty well. I just think in the process, I realized that we skew a little more towards rides, and I think if I got to do it again, I would try to have us do, , the Astro Orbiter and the PeopleMover and Dumbo and maybe even Speedway, like some of those outdoor rides the
[00:16:54] Dana: You know what’d be a really fun one that’s like my favorite to ride while the fireworks are going off is Big Thunder Mountain. And again, this is just one of those things that I have a happy memory of it. So it was just like one of those magical nights, so it’s what I always talk about, but someone else could have the opposite story.
[00:17:14] Dana: Of just riding Big Thunder, ’cause it goes like in and out, and in and out. And just getting that sweet spot of like looking up and seeing a firework is so fun. And it is, I haven’t ridden it since it reopened. Did you? Or was it open when you were there?
[00:17:31] Jessie: It was open. It was open. It was awesome. It was really great. It was so smooth. , Even riding the Barnstormer after that, I felt like, ugh, all shaken up.
[00:17:44] Dana: I know. I’m like, “What is up with the Barnstormer?”
[00:17:47] Jessie: Yeah.
[00:17:49] Dana: Wonder if they’ll update, I wonder if they’ll update that eventually. Well, it’s funny because I always, when I was younger, I liked the rickety-ness of Big Thunder, and I’m just too old. I’m just too old now. , I’m, I really wanna ride the new Muppets coaster, and I’m dreading it ’cause I know my neck is gonna be killing me after.
[00:18:10] Dana: But that’s awesome that you got to ride it. I think that would be a fun one. It’s less chill than something like Dumbo or some- or Magic Carpets or something, but I think that would be a fun fireworks one. ‘Cause not every… I mean, I love Happily Ever After, but I totally get there’s some shows that I watch where I don’t necessarily, , feel something, so I understand if there’s something else, ’cause that’s a great time to ride rides, because everyone else is watching the fireworks, if it’s not a priority for you
[00:18:41] Jessie: Yeah, and my son does seem to enjoy to see the fireworks, and I feel like, seeing them from a ride like you’re describing could be, a very fun, special moment
[00:18:52] Dana: I love that. Next
[00:18:53] Jessie: Yeah, right? That’s part of the plan
[00:18:57] Dana: So how did your Lightning Lanes go for this trip? You used Multi Pass and Single Passes, I think both of the days
[00:19:08] Jessie: Yeah, that’s right. Yeah. On the first day, I had gotten a single pass for Guardians, and at that point, my son said he did wanna ride it, so I bought one for each of us. So we had those.
[00:19:20] Dana: Okay
[00:19:21] Jessie: And then the second day, I bought a single pass for Mine Train for the morning, and then I bought a single pass again for all of us for Rise of the Resistance.
[00:19:35] Dana: You said something about Guardians, like at the time he did wanna write it. Does that mean he changed his mind?
[00:19:42] Jessie: He changed his mind, which I think was the right decision in the end after I got to ride it by myself
[00:19:49] Dana: When did he change his mind? , was he in line and change his mind, or like that day?
[00:19:54] Jessie: It was that day and we weren’t in line, but we were, like, close enough to our return window that it was getting to be time to, to ride it and, to start winding down our time at Epcot to be able to hop over to Magic Kingdom. So, I give him a lot of credit. It– We had taken him on it last year and it was just too fast and too dark and,
[00:20:20] Dana: Yeah
[00:20:21] Jessie: I don’t think he knew about like taking off backwards.
[00:20:25] Jessie: Like, I think I told him about that, but it was– My husband and
[00:20:29] Dana: great that he got on it last time. I mean, I have no… Not that I ever have a problem with my kids not wanting to do something, ever, but I do encourage them to try it if I think that they’ll like it. And then once they do it once, if they say they don’t wanna ride it, I’m like, “Fine.” Like, “You did it.
[00:20:47] Dana: You know that you did not like it.” It’s not like you’re, were too scared to try it and chickened out. My husband has been encouraging my 10-year-old to get on Guardians, and I’m looking at him like, “She is not ready for that.” Sometimes you just know, and sometimes you don’t know. It’s really hard. Kids are very interesting little funny people just like us, and they just don’t know until they try it, so I give him credit for trying it
[00:21:18] Jessie: I do too and figuring out that it wasn’t for him , the day of. I had… Because I had been asking him before I was buying the single pass. I was like, “Do you feel like you’re gonna wanna do it or not?” And
[00:21:30] Dana: Did you even try to, like did one of you ride twice with his MagicBand or something, or did you try to get a refund?
[00:21:38] Jessie: My husband rode twice, , and then that gave me and my son a little bit more of a break, and we went to Club Cool, while he was riding. And yeah,
[00:21:47] Dana: And you had that little moment with the stuffed animal. I love
[00:21:51] Jessie: Exactly.
[00:21:52] Dana: Exactly. So looking back, what was your favorite thing that you did that you’re like, “Oh, next time we come back, , we definitely have to do this again”?
[00:22:03] Jessie: I’m looking at my notes here
[00:22:08] Dana: I’m sure those two days, , completely blurred by
[00:22:12] Jessie: It is a blur. I mean, the parade was really wonderful. The Starlight Parade was wonderful. I would definitely do that again. The
[00:22:21] Dana: I like where you watched it too. I think I’m gonna try to watch where you watched it. It seems like that is a good spot with not a ton of people
[00:22:31] Jessie: Yeah. Yeah, it wasn’t packed or anything, and that’s even considering that in theory it was more crowded than usual because there wasn’t Happily Ever After the following night. But
[00:22:44] Dana: Honestly, a lot of people, it’s so terrible to say, but I have a feeling because it wasn’t like a planned party, it was like for some private event, I bet you a lot of people didn’t even know or realize. I think it gets more crowded on the non-party nights because like people are just more aware.
[00:23:05] Dana: But you wouldn’t even think about it in like mid-May of why would Magic Kingdom close at 5:30? Which is probably why it wasn’t like that crowded, and I feel bad for those people. So good on you for checking that and noticing that. And then you were saying the pool too he
[00:23:22] Jessie: Yeah, I think the pool at Caribbean Beach was definitely, a lot of fun times, just the three of us together. My son loved the slides there, and the zero entry was super handy there. And he always loves using the little life jackets they have, like makes him a little more confident in the water.
[00:23:41] Jessie: And,
[00:23:42] Dana: Yeah, they have really good si- like, they’re good quality life jackets too. They’re not the puddle jumpers for the littler kids, but just so people know, if you think you have to pack those things, , it’s hard if you have, , a two-year-old like me, I prefer those little puddle jumpers with the arms.
[00:23:59] Dana: But in a pinch, they have life jackets from, , extra small, which can fit him, to, , extra large, which could probably fit me. Or, , maybe
[00:24:09] Dana: a… Yeah, right? It’s
[00:24:11] Jessie: Yeah, they’re pretty big.
[00:24:13] Dana: Yeah. So don’t pack those
[00:24:18] Jessie: the right size, so we– he had a bigger one. But,
[00:24:22] Dana: Aw.
[00:24:22] Jessie: we finally got the right size, and that
[00:24:24] Dana: Poor Jude
[00:24:26] Jessie: But it gave him like, a little more confidence. On the last day, he was like, actually swimming, like using the swimming skills he had learned in lessons but hadn’t really tried yet.
[00:24:37] Jessie: So
[00:24:38] Dana: that she’ll be turning, she’ll be turning the same age. She’s turning six in July, and she can swim, but she flails a little. So it’s nice to just have that backup and know that they’re there. And they have the lifeguards there, which is really nice. Would you… ‘Cause I only know this from talking in the community, and you were really helpful with answering other members’ questions about this, but I’m curious, would you use weight magic again for your modifying your lightning lanes?
[00:25:09] Jessie: Yeah, absolutely. I would totally use WaitMagic again. I had gotten a seven-day subscription to WaitMagic because I had heard that it could modify my pre-bookings ahead of time. And I also got Standby Skipper while we were at the park. So I was using both for a while. WaitMagic I found, I don’t know if it’s something technical with- within the Disney feeds or whatever, but it wasn’t really until about, like, midnight or 1:00 AM of each of our park days when Ma- WaitMagic was able to really grab and modify our times.
[00:25:50] Dana: It didn’t modify anything like before you were in Disney? It wasn’t able to change anything?
[00:25:57] Jessie: It wasn’t, but my theory is that no one was giving anything up maybe. , People weren’t… I have no idea. But it consistently, it was only, , midnight or 1:00 AM on both of the nights before that we really started getting kinda, , the perfect time slots. I had kinda mapped things out to work geographically and, kinda make, , little perfect bite combinations in different, geographical areas
[00:26:28] Dana: you weren’t like crisscrossing a ton
[00:26:30] Jessie: Right.
[00:26:31] Jessie: That was something I considered as part of like, we’re gonna have these really long days hopping. Let’s minimize our walking if we can.
[00:26:40] Dana: Can you give like just a general, just in case no one knows what we’re talking about, which I think is gonna be most people. I’ll just really quickly, these are both third-party apps separate to Disney that you can pay for in addition to using Lightning Lane Multi Pass that essentially help you book your Lightning Lanes.
[00:27:00] Dana: But can you explain the difference between the two? Like how did you use Wait Magic versus Standby Skipper?
[00:27:09] Jessie: So, Standby Skipper is an app of its own. And I had used that in the past too and had good results with that. But Standby Skipper is good for grabbing rides when you have a lightning lane open. So, it’s relatively easy to like schedule in the rides that you wanna request and then set it and let Standby Skipper do its thing and grab for you what you want.
[00:27:36] Dana: Like, “Hey, get me, o- once I scan into Dumbo, get me a small world for as soon as possible,” so you don’t have to be on your phone doing it
[00:27:48] Jessie: Exactly. Yeah, especially if you’re near Small World, right? Or like, later tonight get me this other ride because I know we’re gonna be in the other area. Wait Magic was a little different that it’s browser-based. And it’s
[00:28:02] Dana: Did that bother you? ‘Cause I think that’s gonna bother me. Like, the fact that it’s a website and not an app
[00:28:10] Jessie: It didn’t in the end. Like, I think it’s pretty thoughtfully designed that, like, the buttons are big enough that you’re– you know, it’s not impossible just from your phone. Like, it’s actually pretty simple from your phone to set it up. It was a little confusing signing up for it. Like, it seemed more confusing than signing up for Standby Skipper and friending Stand- making Standby Skipper part of your party. It seemed more confusing with that setup, but then the actual, like, booking of your requests or your modifications, that seemed a little more straightforward or more intuitive, really. But before our park days, I had set our pre-bookings to improve, like get even better to where we wanted them to be, like from a geographical and timepoint point of view.
[00:28:59] Jessie: And it was able to grab that stuff for us, and I found that I could– as we’re waiting in line or something, I could still, like ask it to modify something further. You can ask Wait Magic to to book something, like just book any time slot and then keep modifying it earlier and earlier for you.
[00:29:20] Jessie: There are a lot of different options to either like book something new through Wait Magic, modify something existing.
[00:29:29] Dana: Right, like you
[00:29:30] Jessie: can take it a lot of ways
[00:29:32] Dana: Right, like you could have a ride already booked and you want the ride but not that time. Or you could have, maybe you like the time but not the ride. Or you, “Hey, I actually…” Or especially with kids, like, oh, maybe they actually might be scared of Pirates of the Caribbean because, or Haunted Mansion because they didn’t like X, Y, Z.
[00:29:53] Dana: You could just modify it to like Winnie the Pooh or something without having to fiddle on your phone so much. I definitely wanna try both which I think they both have their pluses and minuses it sounds like. Because you were able to get… Like, did you ride very much without a Lightning Lane?
[00:30:11] Dana: It sounded like you got, ’cause you rode Test Track, Big Thunder Soarin’. Were you able to get on Soarin’ with a Lightning Lane?
[00:30:20] Jessie: Oh, yeah. Soren, Spaceship Earth,
[00:30:24] Dana: you do Frozen or Remy on your Epcot day?
[00:30:27] Jessie: We did Remy’s early entry,
[00:30:30] Dana: So did, how was that? Because I know that you didn’t like it, the last experience that you had. Did it go better this time?
[00:30:38] Jessie: It was much better, yes. , The line at the Skyliner at Caribbean Beach was pretty short, so I knew we were, we were kinda… We were closer in the front of the pack when we were waiting to go through security and the turnstiles at Epcot. And I think we w- we went right into the actual queue of Remy’s.
[00:31:02] Jessie: What I had experienced the previous year was being way back in Morocco, so to be right in the queue at the beginning, yeah. And I was kinda pushing for us to do that because I really wanted to see Impressions de France. And it– You can only see it at 9:00 AM or, , the last show of the evening.
[00:31:22] Jessie: And I knew we would’ve hopped, we were going to hop to Magic Kingdom. So that was almost like a mid-morning break for us. We got a mimosa and a few crepes,
[00:31:32] Dana: Oh, nice
[00:31:33] Jessie: Crepes beforehand, and I got to take my mimosa in. And my son was very into the movie. Like, it’s such a nice little movie.
[00:31:42] Jessie: I’d
[00:31:42] Dana: I just love that whole
[00:31:43] Jessie: I was a kid
[00:31:45] Dana: of France in there. It’s just … It’s, it gets a little busy sometimes, but I still like it. It’s worth it. I guess in the morning, like mid-morning, it doesn’t sound like it’s too bad, but I love getting my champagne and it’s just like a nice little break there. What was Jude’s favorite thing of the trip, if you asked him?
[00:32:06] Jessie: He definitely loved Test Track. That was nice that we got to try a new ride, and he loved it so much. I think he liked the swimming a lot. I think he liked the parade. But yeah, he would probably say Test Track
[00:32:20] Dana: I can’t wait to take my kids on that. And I’m gonna have my curly-haired kid too with the picture just covering their face. Good that you reminded me about that, ’cause I have to put her hair back so we can actually see her. This was awesome. I think this is gonna be very helpful for a lot of different reasons.
[00:32:39] Dana: I know there’s a ton of people that debate Caribbean Beach and how the Skyliner will be, early entry, what to do when parks close, or, like, Magic Kingdom closes early, which is coming up really quickly. And just having, , a shorter trip, because a lot of people can’t do… Not that they can’t do a full week, but a lot of people are doing shorter trips where they tack things on like you did with either other family vacations, or maybe they have a conference and they just wanna, , bring the kids for a couple days, or they’re doing a cruise.
[00:33:14] Dana: So I think that’s really helpful. I have yet to do a two-day trip. I would be– I would have no idea what to do. So this was awesome. Thank you very much
[00:33:25] Jessie: Yeah, I’m happy to help. I’m happy to help, and it felt like four days with that nice arrival day and departure day. So
[00:33:32] Dana: Oh, that’s true. That’s
[00:33:33] Jessie: yeah. Yeah.
[00:33:35] Dana: kept it laid back just the way I like it
[00:33:38] Jessie: Yeah, I think I’m a recovering over planner, so yeah
[00:33:43] Dana: the
[00:33:43] Jessie: did our best.
[00:33:46] Dana: I’m gonna hit stop, but you and I will still be here, if that makes sense. I’m just gonna let it upload
My life doesn't revolve around Disney like you may think. I live for my family: my husband and our three kids. In my spare time I like to make my home the best it can be, read on our porch and watch (you guessed it) Disney+.
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Jessie only had two park days, a family visit planned afterward, and an unexpected early park closure that could have completely changed her plans. But somehow, this ended up being one of those Disney trips that felt relaxed, flexible, and full of the moments that mattered most.
In this Disney trip report, Jessie joins me to break down exactly how she approached a short Walt Disney World vacation, from choosing the right resort and park ticket strategy to navigating Lightning Lanes, park hopping, and a few surprises along the way.
If you’ve ever wondered whether a shorter trip can still feel worthwhile, this episode is proof that you don’t need a full week at Disney to have an amazing experience.
In this episode, we cover:
From Skyliner strategy and park hopping to fireworks, parade viewing, and ride priorities, this Disney trip report is packed with practical takeaways for families trying to make the most of a shorter vacation.
And if you’re debating whether a Disney World park hopper is worth the extra cost, or whether Caribbean beach resort is the right fit for your family, Jessie shares exactly what worked, what surprised her, and why she never felt rushed despite having limited time.Come hang out with us over on Instagram @somewhereworthwhile and let us know: if you only had two park days, how would you spend them?
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Podcast music by Podington Bear, track: ‘Filaments’, licensed under CC BY-NC, courtesy of Free Music Archive.
[00:00:00] Dana: Hi, Jessie. Welcome to the Laid Back Magic Way podcast. I know you just got back from Disney World, I wanna say two days ago? When did you get back?
[00:00:12] Jessie: We got back Tuesday morning this past week. It feels like it’s been longer, but we flew back home out of Fort Lauderdale Tuesday morning and got to Albany around lunchtime. And yeah, we’ve been settling back in since
[00:00:28] Dana: I’m excited to talk about your trip because I know we were talking about it because you’re a Laid Back Magic member, so I had a general sense. I saw your original sketch, and then you were thrown a few curve balls. But you’ve been to Disney World before, so it wasn’t like your first time. I’m sure there’s first times for a lot of things, which we’re gonna talk about.
[00:00:49] Dana: But I wanted to ask you, going into it with like a blank slate, what did you know were like the non-negotiables that you definitely wanted to do?
[00:00:59] Jessie: We knew– I think I just knew realistically that this was a Disney trip tacked on to what would be later in the week a, a visit with family in South Florida. So I knew that, we could spay– spend maybe three nights but we had to limit our time. Time was definitely a constraint. I think I knew that I wanted our trip to be kinda ride-heavy.
[00:01:24] Jessie: We’re definitely fans of rides. We started out taking my son to the Magic Kingdom just for the day in the Genie\+ days, and would just hop from ride to ride and have a ton of fun and make a day of it split up- splitting off from visiting family in South Florida. So last year we finally tried our first overnight and then, we wanted to kinda make it even better this time around.
[00:01:50] Jessie: But I knew that I wanted our stay to be ride-heavy. And I know that my son is crazy about Disney pools and swimming, so I knew that we wanted a good bit of pool time in there. So I kinda planned it that our arrival day and our departure day we had a good bit of pool, good bit of pool time fit in
[00:02:13] Dana: Yeah. A six-year-old boy is definitely the perfect age for a lot of pool time and a lot of rides. So what kind of… Well, I’ll ask you this first. What resort did you stay at, and how did you land on that? ‘Cause I know the first time you went, I believe you stayed at Pop Century
[00:02:32] Jessie: That’s right, yeah. So when we went last year, we stayed at Pop Century, and that was great. We loved the Skyliner and everything. And my son totally loved the hippie-dippie pool. But I found that the line at the Skyliner at Pop, it took quite a while to process the morning we were trying to do early entry at Epcot last year, and I feel like we had a fail going to Remy’s.
[00:02:56] Jessie: Like, ended up in this huge line way back by Morocco,
[00:03:00] Dana: Oh, wow.
[00:03:01] Jessie: but didn’t really know… Yes. But didn’t really know what was more normal or not. So I had that in the back of my mind as I was planning this year, and I actually booked the trip with us staying at Pop again. But later I read an article about how Caribbean Beach can be h- a heads above Pop Century as far as the Skyliner goes, that there’s a, I think, a smaller number of peop- capacity, at Caribbean Beach Resort, plus folks kinda distribute themselves to either the Riviera stop if you’re on the northern end or
[00:03:43] Dana: Right.
[00:03:44] Jessie: the regular stop on the other end.
[00:03:46] Jessie: So
[00:03:46] Dana: Because if anyone’s listening and wondering what she’s talking about, there’s multiple resorts on the Skyliner route that will go to Epcot and Hollywood Studios, but they use Caribbean Beach as the hub. So you have to get off at Caribbean Beach and then go whatever direction.
[00:04:03] Dana: So it would, I would assume, already be dispersed, I think is what you’re saying. Like, by the time you’re at Caribbean Beach, there’s less people. So that being your starting point sounds better. So that’s pretty cool. I know I’ve been to Caribbean Beach because I really like Sebastian’s. Did you have a chance to eat there?
[00:04:23] Jessie: Yeah, we actually like thinking about the rhythm of the trip that I wanted and like trying to set an intention of, a thoughtful, like joyful trip together. I had planned it that we would go to Sebastian’s the night of our arrival. And that was great. My husband fell in love with it, and it was a little harder for my son.
[00:04:44] Jessie: He was, wanting to be on my phone and
[00:04:48] Dana: Oh, I
[00:04:49] Dana: know,
[00:04:50] Jessie: hadn’t transitioned into the magic or something
[00:04:53] Dana: I know. Travel.
[00:04:53] Jessie: had been a long travel day, right? , But no, the whole Sebastian’s Bistro experience was great, and it totally won my husband over. , I feel like he totally loved it, all the food and
[00:05:06] Dana: good to get the husband in a good mood just as much as the kid on the first day. Maybe even more so than the kid. ‘Cause travel days are hard even with the screen time too, because you were flying, so he probably was just, like, a zombie at that point. So I totally get it. But I remember when we ate there it was, you just have kind of the stars align and you have a really good night, so I have a happy memory of it.
[00:05:31] Dana: But my husband loved that it was, like, the cheapest meal of the trip, ’cause it was towards the end, and we got the bill and we were like, “Really? Is this right? This can’t be right.” So it’s very affordable. It’s easy to get a reservation. And it’s, it is, like, a night… And we did the same thing. We did it on the day of arrival, and it was just happy vibes.
[00:05:51] Dana: What did you think about Caribbean Beach overall as far as like, when you had to take the bus to Magic Kingdom? Did that all feel good?
[00:06:02] Jessie: It felt pretty good. So that was our, By that point, it was our second morning and our second bus experience because we had taken the bus home after Happily Ever After from Magic Kingdom the night before. So the bus the next morning felt pretty smooth. We were probably some of the only people waiting for the bus at our bus stop.
[00:06:24] Jessie: We had gotten a Little Mermaid room down in Trinidad, I guess. And
[00:06:29] Dana: a good building to be in
[00:06:32] Jessie: Yeah, we loved it. I had put in a request for it and we ended up getting it and, nice to have the new bathroom and the refresh room and all of that.
[00:06:41] Dana: Awesome
[00:06:42] Jessie: But yeah, the bus was relatively simple that morning. And the night before was our first bus experience.
[00:06:50] Jessie: I was bracing myself for like the bus after Happily Ever After and told my husband all about it and Was prepared to book a minivan if we needed, but it actually worked out fine
[00:07:05] Dana: It’s better to expe- I mean, you wanna have a positive attitude. I was thinking about this the other day. I was like, ’cause I’m a pessimist, I just am, or like Murphy’s Law. , Oh, it’s gonna be this, it’s gonna be that. So it’s like you don’t wanna be like that. You wanna have a positive attitude, but at the same time, like underneath of it, un- underneath of the positive attitude, be prepared that the worst could happen, and then you’ll be pleasantly surprised and happy when that doesn’t happen.
[00:07:35] Dana: Walk me through your tickets and the way that you structured the park, ’cause I know you didn’t go into the parks the day you got there, and then you had two-day park hoppers. What did that look like? How did you structure that out?
[00:07:49] Jessie: So I ended up realizing we could plan it with just two days of park hoppers just because of our limited time and trying to keep us at just three nights at the resort. I decided we really wanted to hit Magic Kingdom and Epcot and Hollywood Studios, and I felt like having two days of park hoppers was, how we could accomplish that. So I think I had booked those park hoppers from the start, and I think it felt like an indulgence when I booked them from the start. You pay a little more, than… I think there was even– There were all these deals that was at the beginning of 2026, like there might have been a three, three, four-park, four-night, kind of promo and a different like three-park, three-day maybe without Magic Kingdom promo.
[00:08:43] Jessie: So it felt a little like indulgent to book two days of park hoppers. But when I think, it was what worked best for our schedule, but also when I found out that Magic Kingdom was closing early
[00:08:56] Dana: Yes
[00:08:57] Jessie: The, our Magic Kingdom day, then that kind of– it was a relief to know that the park hoppers were really required to do what we had to do.
[00:09:07] Dana: Yeah, like you
[00:09:08] Jessie: What we wanted to do,
[00:09:10] Dana: especially because you wanted to do Phantasmic and Happily Ever After, I think
[00:09:17] Jessie: Yeah, we’d never done Fantasmic! before, and I’ve heard people say it has a few kind of scary or dark moments, but my son is totally into Halloween and scary stuff, so it sounded like it would be up our alley. So I wanted to do that. I knew it would probably be an easy Skyliner ride home. And Happily Ever After is funny.
[00:09:37] Jessie: I felt like we had to like, give it another chance or try it again. Like, I feel like we had seen it previously right before, a two-and-a-half-hour drive to see family. This was probably, our last trip or a long day trip. So I felt like we had to try it again. We definitely wanted to see Starlight, which ended up being awesome.
[00:10:02] Dana: Wait to see that. I’m excited about that
[00:10:04] Jessie: It was great. We had just– We had pretty much come over from Epcot and pretty much posted up between the confectionary and the theater, maybe the Town Square Theater where you meet Mickey. And we met another family there and we’re right by the curb, and my son was sharing like glow bracelets with-
[00:10:28] Dana: Oh, I love that
[00:10:29] Jessie: family. And yeah, that was one of those nice little Disney moments, but it was nice to have, him have some interaction and, some fun while we were waiting for the parade to start.
[00:10:40] Dana: kid problems, right? You’re like… disney’s a great place to be an only child, ’cause when we used to go before we had kids, we would just go with my niece, who’s an only child, and she loved it. She loved getting spoiled, and then you have all the kids that you can play with, but then you don’t have to, , share your food or your toys with, and be like, “See you later.”
[00:11:01] Dana: So I’m sure Jude was having a blast. That was one of the things that when I was looking at questions you posted in the community, was you had your original sketch, then you saw that Magic Kingdom was closing early on the, like the night that you thought to plan for the Starlight Parade and Happily Ever After, it closed at 5:30.
[00:11:23] Dana: And I think this is a great thing to talk about, because this is our future going into the August, September, October, November, December months, is Magic Kingdom closes, , over 60 times it closes early for the rest of the year. So I know everyone’s going to be having this thought of, “Oh, we’re gonna do this,” and then they’re gonna check the times and realizes that it closes early.
[00:11:49] Dana: And like you said, you felt indulgent with the Park Hopper, but it was a requirement to end up doing what you wanted to do anyway. So it was like a happy accident. But you were able to move things around and not get, , pigeonholed into your plans and be flexible. So you did Epcot the first day.
[00:12:12] Dana: So the first morning was Epcot, then hopped to Magic Kingdom. Did you take a break at all, or did you just take the monorail? What did you do?
[00:12:22] Jessie: We had a little bit of a break at Epcot. It was raining on and off, and we I think we went to Connections and got some food and kinda camped out there for a little bit while it was raining. I feel like they have a big, , bench seat where my son could just, , get with his new, , Coke can pillow from Club Cool and,
[00:12:43] Dana: Oh yeah, I know the benches you’re talking about. We end up there a lot too. Everybody does.
[00:12:48] Jessie: It was a good place for him to kinda relax and us to be out of the rain and, , rest up a little before, before moving on. But it helped to know that we could have gone back to the resort if we had to, but I knew we, we probably wouldn’t have to. And I had tried to plan our itinerary for the day geographically, , just kinda making one big figure eight or something around Epcot. And I thought we would have gone all the way back through World Showcase at the end, and I realized, oh, maybe we’ll walk to Beach Club and take the bus to Magic Kingdom. But it actually turned out that we used a lot of our time for rides.
[00:13:32] Dana: Mm-hmm.
[00:13:33] Jessie: I had gotten Test Track as a Lightning Lane, and since it was raining on and off, I lost it twice as a Lightning Lane.
[00:13:43] Jessie: And I feel like the last time that I– the last time that I traveled to Disney that when I had a Multi-Experience Pass, I thought that it showed up where my Lightning Lanes were. But this time around, that was showing up in the My Plans tab. So I hadn’t realized I could just use it right away. So we had been at Connections, it had been rainy, and we were about to get on the monorail to go to Magic Kingdom, and I saw two guest services people, and my husband was like, “Why don’t you just ask?”
[00:14:17] Jessie: I asked them and I found out, , oh, that was actually our Multi-Experience Pass. So at that point, we got to go do Test Track twice, and my son– None of us had ever done it and,
[00:14:29] Dana: Did he love it?
[00:14:31] Jessie: it. Yeah, he really did.
[00:14:33] Dana: That’s like the perfect ride for a three-person family too, ’cause it’s three seats across, which makes it so fun. And
[00:14:39] Jessie: We have some
[00:14:40] Dana: is just a good age for that
[00:14:42] Jessie: Yeah, we have some fun photos from it, and he has kinda long curly hair, and when you go outside, and really pick up speed, he was like, “My hair,” and it was all over his
[00:14:53] Dana: Could you even see his face? ‘Cause my daughter, it just goes right in front of her face. You don’t even see anything. I’m like, “You need like a hair band or something.”
[00:15:00] Jessie: Right. Yeah. Yeah, it was kinda like that. But he loved it, so the fact we got to just ride it twice in a row right then was pretty wonderful.
[00:15:09] Dana: That’s a happy mistake. Worked out. Yeah.
[00:15:12] Jessie: Yes
[00:15:13] Dana: So then I, we were talking about it before and I went on a tangent, but you were talking about how you wanted to give Happily Ever After a second chance it seems like. W- were you able… Did you stay where you were, where you watched the Starlight Parade, or did you move to watch Happily Ever After?
[00:15:33] Jessie: So we, we moved a little bit. We moved to the center of that circle in the middle of Town Square. And in the break between the end of the parade and the beginning of the fireworks, we changed my son into pajamas and, tried to be strategic about leaving the park relatively quickly after the fireworks were done. And I think I just chose that spot back in Town Square as a, easy exit kind of point. And the view
[00:16:04] Dana: far in the front
[00:16:05] Jessie: Right. Yeah. And the view was pretty good. , We could see, some of the fireworks down Main Street. I thought we would see more projections on Main Street. I don’t know if it was because the time of year and it’s so light out in the evening in May, but it seemed like a lot of the projections on Main Street were the, the half closer to the castle rather than back where we were.
[00:16:29] Dana: Okay
[00:16:30] Jessie: but yeah, it went pretty well. I just think in the process, I realized that we skew a little more towards rides, and I think if I got to do it again, I would try to have us do, , the Astro Orbiter and the PeopleMover and Dumbo and maybe even Speedway, like some of those outdoor rides the
[00:16:54] Dana: You know what’d be a really fun one that’s like my favorite to ride while the fireworks are going off is Big Thunder Mountain. And again, this is just one of those things that I have a happy memory of it. So it was just like one of those magical nights, so it’s what I always talk about, but someone else could have the opposite story.
[00:17:14] Dana: Of just riding Big Thunder, ’cause it goes like in and out, and in and out. And just getting that sweet spot of like looking up and seeing a firework is so fun. And it is, I haven’t ridden it since it reopened. Did you? Or was it open when you were there?
[00:17:31] Jessie: It was open. It was open. It was awesome. It was really great. It was so smooth. , Even riding the Barnstormer after that, I felt like, ugh, all shaken up.
[00:17:44] Dana: I know. I’m like, “What is up with the Barnstormer?”
[00:17:47] Jessie: Yeah.
[00:17:49] Dana: Wonder if they’ll update, I wonder if they’ll update that eventually. Well, it’s funny because I always, when I was younger, I liked the rickety-ness of Big Thunder, and I’m just too old. I’m just too old now. , I’m, I really wanna ride the new Muppets coaster, and I’m dreading it ’cause I know my neck is gonna be killing me after.
[00:18:10] Dana: But that’s awesome that you got to ride it. I think that would be a fun one. It’s less chill than something like Dumbo or some- or Magic Carpets or something, but I think that would be a fun fireworks one. ‘Cause not every… I mean, I love Happily Ever After, but I totally get there’s some shows that I watch where I don’t necessarily, , feel something, so I understand if there’s something else, ’cause that’s a great time to ride rides, because everyone else is watching the fireworks, if it’s not a priority for you
[00:18:41] Jessie: Yeah, and my son does seem to enjoy to see the fireworks, and I feel like, seeing them from a ride like you’re describing could be, a very fun, special moment
[00:18:52] Dana: I love that. Next
[00:18:53] Jessie: Yeah, right? That’s part of the plan
[00:18:57] Dana: So how did your Lightning Lanes go for this trip? You used Multi Pass and Single Passes, I think both of the days
[00:19:08] Jessie: Yeah, that’s right. Yeah. On the first day, I had gotten a single pass for Guardians, and at that point, my son said he did wanna ride it, so I bought one for each of us. So we had those.
[00:19:20] Dana: Okay
[00:19:21] Jessie: And then the second day, I bought a single pass for Mine Train for the morning, and then I bought a single pass again for all of us for Rise of the Resistance.
[00:19:35] Dana: You said something about Guardians, like at the time he did wanna write it. Does that mean he changed his mind?
[00:19:42] Jessie: He changed his mind, which I think was the right decision in the end after I got to ride it by myself
[00:19:49] Dana: When did he change his mind? , was he in line and change his mind, or like that day?
[00:19:54] Jessie: It was that day and we weren’t in line, but we were, like, close enough to our return window that it was getting to be time to, to ride it and, to start winding down our time at Epcot to be able to hop over to Magic Kingdom. So, I give him a lot of credit. It– We had taken him on it last year and it was just too fast and too dark and,
[00:20:20] Dana: Yeah
[00:20:21] Jessie: I don’t think he knew about like taking off backwards.
[00:20:25] Jessie: Like, I think I told him about that, but it was– My husband and
[00:20:29] Dana: great that he got on it last time. I mean, I have no… Not that I ever have a problem with my kids not wanting to do something, ever, but I do encourage them to try it if I think that they’ll like it. And then once they do it once, if they say they don’t wanna ride it, I’m like, “Fine.” Like, “You did it.
[00:20:47] Dana: You know that you did not like it.” It’s not like you’re, were too scared to try it and chickened out. My husband has been encouraging my 10-year-old to get on Guardians, and I’m looking at him like, “She is not ready for that.” Sometimes you just know, and sometimes you don’t know. It’s really hard. Kids are very interesting little funny people just like us, and they just don’t know until they try it, so I give him credit for trying it
[00:21:18] Jessie: I do too and figuring out that it wasn’t for him , the day of. I had… Because I had been asking him before I was buying the single pass. I was like, “Do you feel like you’re gonna wanna do it or not?” And
[00:21:30] Dana: Did you even try to, like did one of you ride twice with his MagicBand or something, or did you try to get a refund?
[00:21:38] Jessie: My husband rode twice, , and then that gave me and my son a little bit more of a break, and we went to Club Cool, while he was riding. And yeah,
[00:21:47] Dana: And you had that little moment with the stuffed animal. I love
[00:21:51] Jessie: Exactly.
[00:21:52] Dana: Exactly. So looking back, what was your favorite thing that you did that you’re like, “Oh, next time we come back, , we definitely have to do this again”?
[00:22:03] Jessie: I’m looking at my notes here
[00:22:08] Dana: I’m sure those two days, , completely blurred by
[00:22:12] Jessie: It is a blur. I mean, the parade was really wonderful. The Starlight Parade was wonderful. I would definitely do that again. The
[00:22:21] Dana: I like where you watched it too. I think I’m gonna try to watch where you watched it. It seems like that is a good spot with not a ton of people
[00:22:31] Jessie: Yeah. Yeah, it wasn’t packed or anything, and that’s even considering that in theory it was more crowded than usual because there wasn’t Happily Ever After the following night. But
[00:22:44] Dana: Honestly, a lot of people, it’s so terrible to say, but I have a feeling because it wasn’t like a planned party, it was like for some private event, I bet you a lot of people didn’t even know or realize. I think it gets more crowded on the non-party nights because like people are just more aware.
[00:23:05] Dana: But you wouldn’t even think about it in like mid-May of why would Magic Kingdom close at 5:30? Which is probably why it wasn’t like that crowded, and I feel bad for those people. So good on you for checking that and noticing that. And then you were saying the pool too he
[00:23:22] Jessie: Yeah, I think the pool at Caribbean Beach was definitely, a lot of fun times, just the three of us together. My son loved the slides there, and the zero entry was super handy there. And he always loves using the little life jackets they have, like makes him a little more confident in the water.
[00:23:41] Jessie: And,
[00:23:42] Dana: Yeah, they have really good si- like, they’re good quality life jackets too. They’re not the puddle jumpers for the littler kids, but just so people know, if you think you have to pack those things, , it’s hard if you have, , a two-year-old like me, I prefer those little puddle jumpers with the arms.
[00:23:59] Dana: But in a pinch, they have life jackets from, , extra small, which can fit him, to, , extra large, which could probably fit me. Or, , maybe
[00:24:09] Dana: a… Yeah, right? It’s
[00:24:11] Jessie: Yeah, they’re pretty big.
[00:24:13] Dana: Yeah. So don’t pack those
[00:24:18] Jessie: the right size, so we– he had a bigger one. But,
[00:24:22] Dana: Aw.
[00:24:22] Jessie: we finally got the right size, and that
[00:24:24] Dana: Poor Jude
[00:24:26] Jessie: But it gave him like, a little more confidence. On the last day, he was like, actually swimming, like using the swimming skills he had learned in lessons but hadn’t really tried yet.
[00:24:37] Jessie: So
[00:24:38] Dana: that she’ll be turning, she’ll be turning the same age. She’s turning six in July, and she can swim, but she flails a little. So it’s nice to just have that backup and know that they’re there. And they have the lifeguards there, which is really nice. Would you… ‘Cause I only know this from talking in the community, and you were really helpful with answering other members’ questions about this, but I’m curious, would you use weight magic again for your modifying your lightning lanes?
[00:25:09] Jessie: Yeah, absolutely. I would totally use WaitMagic again. I had gotten a seven-day subscription to WaitMagic because I had heard that it could modify my pre-bookings ahead of time. And I also got Standby Skipper while we were at the park. So I was using both for a while. WaitMagic I found, I don’t know if it’s something technical with- within the Disney feeds or whatever, but it wasn’t really until about, like, midnight or 1:00 AM of each of our park days when Ma- WaitMagic was able to really grab and modify our times.
[00:25:50] Dana: It didn’t modify anything like before you were in Disney? It wasn’t able to change anything?
[00:25:57] Jessie: It wasn’t, but my theory is that no one was giving anything up maybe. , People weren’t… I have no idea. But it consistently, it was only, , midnight or 1:00 AM on both of the nights before that we really started getting kinda, , the perfect time slots. I had kinda mapped things out to work geographically and, kinda make, , little perfect bite combinations in different, geographical areas
[00:26:28] Dana: you weren’t like crisscrossing a ton
[00:26:30] Jessie: Right.
[00:26:31] Jessie: That was something I considered as part of like, we’re gonna have these really long days hopping. Let’s minimize our walking if we can.
[00:26:40] Dana: Can you give like just a general, just in case no one knows what we’re talking about, which I think is gonna be most people. I’ll just really quickly, these are both third-party apps separate to Disney that you can pay for in addition to using Lightning Lane Multi Pass that essentially help you book your Lightning Lanes.
[00:27:00] Dana: But can you explain the difference between the two? Like how did you use Wait Magic versus Standby Skipper?
[00:27:09] Jessie: So, Standby Skipper is an app of its own. And I had used that in the past too and had good results with that. But Standby Skipper is good for grabbing rides when you have a lightning lane open. So, it’s relatively easy to like schedule in the rides that you wanna request and then set it and let Standby Skipper do its thing and grab for you what you want.
[00:27:36] Dana: Like, “Hey, get me, o- once I scan into Dumbo, get me a small world for as soon as possible,” so you don’t have to be on your phone doing it
[00:27:48] Jessie: Exactly. Yeah, especially if you’re near Small World, right? Or like, later tonight get me this other ride because I know we’re gonna be in the other area. Wait Magic was a little different that it’s browser-based. And it’s
[00:28:02] Dana: Did that bother you? ‘Cause I think that’s gonna bother me. Like, the fact that it’s a website and not an app
[00:28:10] Jessie: It didn’t in the end. Like, I think it’s pretty thoughtfully designed that, like, the buttons are big enough that you’re– you know, it’s not impossible just from your phone. Like, it’s actually pretty simple from your phone to set it up. It was a little confusing signing up for it. Like, it seemed more confusing than signing up for Standby Skipper and friending Stand- making Standby Skipper part of your party. It seemed more confusing with that setup, but then the actual, like, booking of your requests or your modifications, that seemed a little more straightforward or more intuitive, really. But before our park days, I had set our pre-bookings to improve, like get even better to where we wanted them to be, like from a geographical and timepoint point of view.
[00:28:59] Jessie: And it was able to grab that stuff for us, and I found that I could– as we’re waiting in line or something, I could still, like ask it to modify something further. You can ask Wait Magic to to book something, like just book any time slot and then keep modifying it earlier and earlier for you.
[00:29:20] Jessie: There are a lot of different options to either like book something new through Wait Magic, modify something existing.
[00:29:29] Dana: Right, like you
[00:29:30] Jessie: can take it a lot of ways
[00:29:32] Dana: Right, like you could have a ride already booked and you want the ride but not that time. Or you could have, maybe you like the time but not the ride. Or you, “Hey, I actually…” Or especially with kids, like, oh, maybe they actually might be scared of Pirates of the Caribbean because, or Haunted Mansion because they didn’t like X, Y, Z.
[00:29:53] Dana: You could just modify it to like Winnie the Pooh or something without having to fiddle on your phone so much. I definitely wanna try both which I think they both have their pluses and minuses it sounds like. Because you were able to get… Like, did you ride very much without a Lightning Lane?
[00:30:11] Dana: It sounded like you got, ’cause you rode Test Track, Big Thunder Soarin’. Were you able to get on Soarin’ with a Lightning Lane?
[00:30:20] Jessie: Oh, yeah. Soren, Spaceship Earth,
[00:30:24] Dana: you do Frozen or Remy on your Epcot day?
[00:30:27] Jessie: We did Remy’s early entry,
[00:30:30] Dana: So did, how was that? Because I know that you didn’t like it, the last experience that you had. Did it go better this time?
[00:30:38] Jessie: It was much better, yes. , The line at the Skyliner at Caribbean Beach was pretty short, so I knew we were, we were kinda… We were closer in the front of the pack when we were waiting to go through security and the turnstiles at Epcot. And I think we w- we went right into the actual queue of Remy’s.
[00:31:02] Jessie: What I had experienced the previous year was being way back in Morocco, so to be right in the queue at the beginning, yeah. And I was kinda pushing for us to do that because I really wanted to see Impressions de France. And it– You can only see it at 9:00 AM or, , the last show of the evening.
[00:31:22] Jessie: And I knew we would’ve hopped, we were going to hop to Magic Kingdom. So that was almost like a mid-morning break for us. We got a mimosa and a few crepes,
[00:31:32] Dana: Oh, nice
[00:31:33] Jessie: Crepes beforehand, and I got to take my mimosa in. And my son was very into the movie. Like, it’s such a nice little movie.
[00:31:42] Jessie: I’d
[00:31:42] Dana: I just love that whole
[00:31:43] Jessie: I was a kid
[00:31:45] Dana: of France in there. It’s just … It’s, it gets a little busy sometimes, but I still like it. It’s worth it. I guess in the morning, like mid-morning, it doesn’t sound like it’s too bad, but I love getting my champagne and it’s just like a nice little break there. What was Jude’s favorite thing of the trip, if you asked him?
[00:32:06] Jessie: He definitely loved Test Track. That was nice that we got to try a new ride, and he loved it so much. I think he liked the swimming a lot. I think he liked the parade. But yeah, he would probably say Test Track
[00:32:20] Dana: I can’t wait to take my kids on that. And I’m gonna have my curly-haired kid too with the picture just covering their face. Good that you reminded me about that, ’cause I have to put her hair back so we can actually see her. This was awesome. I think this is gonna be very helpful for a lot of different reasons.
[00:32:39] Dana: I know there’s a ton of people that debate Caribbean Beach and how the Skyliner will be, early entry, what to do when parks close, or, like, Magic Kingdom closes early, which is coming up really quickly. And just having, , a shorter trip, because a lot of people can’t do… Not that they can’t do a full week, but a lot of people are doing shorter trips where they tack things on like you did with either other family vacations, or maybe they have a conference and they just wanna, , bring the kids for a couple days, or they’re doing a cruise.
[00:33:14] Dana: So I think that’s really helpful. I have yet to do a two-day trip. I would be– I would have no idea what to do. So this was awesome. Thank you very much
[00:33:25] Jessie: Yeah, I’m happy to help. I’m happy to help, and it felt like four days with that nice arrival day and departure day. So
[00:33:32] Dana: Oh, that’s true. That’s
[00:33:33] Jessie: yeah. Yeah.
[00:33:35] Dana: kept it laid back just the way I like it
[00:33:38] Jessie: Yeah, I think I’m a recovering over planner, so yeah
[00:33:43] Dana: the
[00:33:43] Jessie: did our best.
[00:33:46] Dana: I’m gonna hit stop, but you and I will still be here, if that makes sense. I’m just gonna let it upload
I've planned our family vacations to Walt Disney World, ranging in ages, sizes, and circumstances; without kids, with one kid, and now with two! From these trips, I've learned what not to do and want to share them with you.
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