Should You Run Disney Wine & Dine? First-Timer Tips, Training & After-Party Survival

Is Disney Wine & Dine Half Marathon Weekend the best runDisney race weekend for first-timers? In this episode of Extraordinary Strides, Christine kicks off a four-part guide to the Walt Disney World runDisney race weekends with a deep dive into Wine & Dine.

By the time this episode airs, most current registration dates have passed, so this conversation is perfect for future race planning, charity bib decisions, and runners trying to decide which runDisney weekend actually fits their goals, training season, travel budget, and personality.

Christine is joined by two runners who love Wine & Dine for very different reasons. Allegra shares why Wine & Dine was a joyful first half marathon experience, what northern runners should know about training for Florida humidity, and why this weekend can feel lower pressure than other runDisney events. Wendy brings the perspective of an experienced runDisney runner who has completed every current Walt Disney World race weekend and still chooses Wine & Dine as her favorite.

In this episode, we cover:

• Why Wine & Dine may be a great first runDisney weekend
• How it compares to Marathon Weekend, Princess Weekend, and Springtime Surprise
• What northern runners should know about heat, humidity, and Florida weather
• Why the after-party is part of the magic, but also requires a plan
• Who Wine & Dine is best for
• Who may want to choose a different runDisney weekend
• Tips for training, costumes, packing, and race weekend strategy

If you are considering a future Wine & Dine registration, looking at charity bibs, or dreaming about your first runDisney race, this episode will help you decide whether this flavorful fall race weekend belongs on your calendar.

Grab Coach Christine’s free runDisney Challenge Training Guide here:
https://extraordinarystrides.com/rundisney/

Transcript

Welcome And Series Roadmap

SPEAKER_01 0:01

Welcome back to Extraordinary Strides, where we celebrate everyday runners doing extraordinary things, and today it'll be one magical mile at a time. Today we're gonna kick off a special four-part guide to the Walt Disney World Run Disney race weekends. And we're starting with one that has a very specific personality, the wine and dine half marathon weekend. Now, a quick note before anyone starts panic refreshing the registration pages. By the time this episode airs, most of this season's upcoming season's general registration dates have already passed, with springtime surprise being the one that may still be ahead depending on when you're listening. So this series is not just about this upcoming year. This is for future planning or charity fib decisions, dream board building, or for anyone trying to figure out which Run Disney weekend actually fits their life, their training, their budget, and their vibe. Because here's the thing all Run Disney weekends have magic. They all have early alarms, costumes, character stops, portable potty strategy, and finish line medals, but they also have a really specific, wonderful vibe. So they don't all feel the same. Marathon Weekend has big goal energy, Princess Weekend has sparkle emotion, and a lot of main character magic. Springtime surprise is the wildcard weekend with nostalgia, shorter distances, and curveballs, but wine and dine. Wine and dine is the flavorful one, the playful one, the come for the miles and stay for Eve COT one. It can be a beautiful first half marathon, like it was for me. It can be a lower pressure weight experience for on Disney, and it can be a great first challenge weekend. And depending on where you live, it may land at a really interesting point in your training year. And we're gonna learn all about that because first you're gonna hear from Allegra Lingo, who brings the perspective of someone who chose Wine and Dine as her first half marathon and trains from Minnesota, which means she knows a thing or two about showing up to Florida prepared for weather whiplash. Then you'll hear from Wendy Castleman, who has experienced every current Walt Disney World Run Disney weekend. She completed a full perfect Run Disney season and still says that if you had to choose just one, wine and dine should be it. Together they're gonna give us two really helpful lenses, the runner who found Wine and Dine as a joyful entry point, and the experienced Run Disney runner who keeps coming back because the weekend still feels special. So whether you're dreaming about your first Run Disney race, debating a charity bib, planning for a future season, and you most definitely need to if you want to get in on one of these races, or just wondering if wine and dine belongs on your running bucket list, this episode is for you. So let's get started with Allegra and talk about Wine and Dine and why it's the most deliciously low pressure gateway into Run Disney Magic. Allegra,

Allegra Finds Run Disney Magic

SPEAKER_01 2:50

I am so excited to have you here because I feel like you bring the exact lens that we need for wine and dine. You have experienced several Run Disney weekends, right? Um yes. And when I asked the question, what would you choose if you only had one? It seemed like it was a no-brainer for you. You were all about the wine and dine life.

SPEAKER_00 3:09

Total, total no-brainer for me. I am indeed. I am like the poster child for wine and dine. So I I love that weekend. Uh this year, 2026 will be my fifth weekend, right, fifth year running it in a row. Um, I just absolutely adore it from bottom to top.

SPEAKER_01 3:27

I want to get into directly into Ren Disney, but I think it's really important that we first talk about you, how you got into the running world and what that running world, how it brought you to Ren Disney.

SPEAKER_00 3:38

Yeah, so so my sister has been a runner, I would say, for the past almost 20 years. And um, so she started getting into it kind of in her early 20s, and I just thought it was so impressive, yeah, you know, and um she signed up uh for Dopey in 2017, and um my wife was also getting into running at the time as well. So my sister was doing Dope. My wife was signed up for her first half. We had, you know, uh us and our daughter, who was two at the time, and then my sister and her now husband, my parents, uh, my aunt came. So we had this like whole group of us down there, and like we'd never done Run Disney. We yeah, we signed Matilda, it's my daughter, uh, up for the kids' races as well. We were just we were all in, right? And if you've been around one dis Run Disney long enough, you know that 2017 was the year that they canceled the half uh because of uh severe thunderstorms and everything. And uh so my wife likes to say that uh she didn't run a half marathon, she ran a half of a marathon. Uh and uh my sister uh qualified for Boston because she was so mad that that was a big thing. Shut the front door. So she ran a BQ time at the next time at Ron Disney during her Dope weekend, just because she had so much pent-up energy from that half being canceled. And and so, like, it was so fun to just be around, you know, the everything from the kids' races to you know cheering for you know the full and everything. But I think my favorite moment was the day of the half, and you know, so many people, especially ones people who had signed up for Dopey, were like, I'm gonna get that race in regardless of the weather that day. And so people were running, you know, the loop around Caribbean Beach or you know, um pop and art of animation, all that stuff. I happened to be up at Contemporary, and there were some people running the loop up there, and there were these two women who had, you know, those like old school plastic fold-out lawn chairs, right? And they were sitting there with these Mickey hand clappers, and every time a runner would go by, they'd be ringing those, going, Yes, you're doing it, you're doing it! And I was like, What's happening here? And they were like, Well, our favorite part of Run Disney is just supporting people. So we figured we would just come out here and support them. And I think I have a video like they're sitting there with their cocktails in one hand, their Mickey clappers in the other, just randomly cheering for people. I was like, Oh, I gotta get in on this. Um, so fast forward a couple years, 2019. Uh, my wife was all, I'm gonna run my first actual marathon, not just half of it. I'm gonna do the whole thing. And my sister was like, Well, I'll do the half. I could I could do the half. And I was like, Well, I might as well do something. Um, so I I have I was I was like, I had never run before in my entire life. Yeah, you know, I'm I'm the one who's you know you know over at the bar cheering, you know, and whatever.

SPEAKER_01 6:46

Very important role as well.

SPEAKER_00 6:47

We're not gonna take that away. Everybody is absolutely integral. Um, and I had meant to sign up for the 5K, missed out on that, signed up for the 10k. I was like, well, here we go. Um we had, you know, our daughter was like four. I didn't train, I had no idea what I was doing. Um, I made it through. Uh, you know, just like what is even what is even happening right now. Um, but there was something in me, I don't know if it was like running out of Epcot. I remember they had like Mary Poppins and the quick carousel horses like just up there on the overpass. I'm like, what is this magic? I'm so tired and I don't care. This is amazing. Um, and it was and I was dressed as Lewis Robinson and who's like my deep cut favorite Disney character. And I'm like, this is just this is so great. I'm gonna be in so much pain. Why are the toilets so low at Disney for like the next week, you know? But um there was something really, really special about it, you know. Um, and then I promptly forgot that I actually enjoyed myself uh until Wina died in 2022. And the theme for the half marathon was the movie Soul. And uh I I am a professional musician as well as all the other stuff that I do. I'm a saxophonist. Um my mom had passed away just a year before. I think that was the last Disney movie she saw before she passed away. She was also a musician, a trumpet player, and I looked at the theme and went, well, I guess I'm running a half marathon. Um, so signed up. Um, I dressed as Yeeha Bob, if you've ever seen him on Port Orleans Riverside at River Roose, uh, because he is my favorite Disney musician. So yeah, you know, I found my old suspenders from like high school jazz band and like, you know, my tie with the music, you know, musical instruments all over it, and and just got out there and did my thing, and I just kind of haven't stopped since then. And I just I just it's just so special. I know you're totally gonna edit so much of this long and meandering. Or not at all. But um, yeah, it's just it's so much fun. And there, you know, I've tried to run a couple local races around here, and I'm just like, no, this ain't worth it, you know. So I train in Minnesota um for running in Florida, uh, at least. Yeah, you know, at least I try to do at least two weekends a year. I'm trying to up that for next season. But um, but yeah, it's it's just it's special. It's special. And the people who do this are, you know, they're they're magical, what do I want to say? Not magical idiots, but that's very close to it, you know.

SPEAKER_01 9:29

Well, there are some folks that might make the statement that we're not the most intelligent crew in the entire world.

SPEAKER_00 9:37

Um, yeah, why is this a good idea to get up at 2.30 in the morning to run for it? And and until you do it, like you cannot understand that just the adrenaline and the satisfaction. And you know, I don't think I have a single photo from Run Disney during the runs that I just don't have the biggest smile on my face, you know, because you're out there, you're just enjoying it, you know?

SPEAKER_01 10:03

There's joy, like there's literal joy. I mean, I know we recently with Springtime Surprise had joy um from Inside Out, but no, there truly is joy in all of these runs, which is we're seeing is why we know they're so popular, why they sell out. But we do know there's also folks that can maybe only spend their time,

Why Wine And Dine Feels Different

SPEAKER_01 10:20

energy, dollars, PTO on one. So, why do you feel like wine and done is the one that people should maybe target if they only had that one race weekend?

SPEAKER_00 10:29

Yeah, I think there's just this really great energy behind it because if you are someone who lives in the south, right, this is kind of your kickoff to your race season every year, right? So that weather is finally cooling down enough that you can devote the time outside to get those trading mile, you know, those miles in for the season and everything. And so for a number of southern runners, you know, this might be their first race in a few months. And so that, you know, there's that energy that comes with that. Um, but for people like me who uh, you know, I'm in Minnesota, um, you know, where I mean it was a it was a balmy 31 degrees when I woke up this morning. And it's what, May 7th? May 7th, yeah. Um you know, this is kind of the end of our outside trading season. And so either way you look at it, I really feel like this weekend is really a celebration of what you have done or what you are about to do, wherever wherever that weekend falls in your, you know, in your personal running season.

SPEAKER_01 11:27

Okay. So it has both kind of like incoming freshman vibes, or it has a little bit of that senior cap off, is what I'm hearing you say, kind of a thing. You got it. I think I think so. Yep. Okay, very cool. Um, would you say that there is things that people let's talk specifically from the northern lens that people should take into consideration? Preparing and training in your summers and coming down here in Florida. It sometimes we get blessed by the weather gods and it can be a little bit cooler. Sometimes it's still very hot and humid for all the race weekends. How how would you suggest that folks maybe prepare?

SPEAKER_00 12:06

Um, well, for wine and dine specifically, it's really just devoting your your mileage during the summer and the fall to being outside. Um, I I think I think that's really just key. You know, get off that treadmill, get outside, get into the into the parks or around your neighborhood or your city or whatever it happens to be. Um, you know, rain or shine, yeah, you know, uh, you know, if you're coming from up north, uh, because getting those outside miles and you know, I mean, we don't get humidity like Florida does, but fairly close, yeah, you know, during those summer months and having that experience of running in high humidity, even though it's nobody's favorite thing, it does get you ready to, you know, to run down in Florida in the fall.

SPEAKER_01 12:54

Yeah, I would say it's probably the easiest I won't say easiest. There's nothing easy about training for any race, right? But it's the one that maybe uh translates the most because I think that there's always that challenge of folks that are training up north for any of the other distances for Marathon Weekend or Princess or Springtime Surprise, where there is a shock to the system coming down here. And it sounds like with Wine and Dine, because of where it's at in that fall, it it likely has a comparable um to what you've been training in.

SPEAKER_00 13:22

Of course, we're just a little bit uh a little bit shorter of an, you know, um what's the word I'm looking for? Uh not yeah, you know, getting used to a time. There's a word that starts with an A that has just left my brain. Um but acclimation. There's a little bit less of an acclimation um, you know, when you're running wine and dine versus, well, I just came down and ran springtime surprise as well. And um yeah, you know, I actually came down six days, I think six days before my first race, um, because I learned my lesson two years ago during Wine and Dine, where I hadn't done that, just kind of showed up, you know, the day before the expo started. And going from, you know, you know, the balming, you know, 35 degrees, uh, you know, where you know, I've been able to get some outside run-ins, but very cold to then running in, you know, 95% humidity and you know, low 70s is such a shock to the system that um that it makes a lot, it makes it a lot harder for, I think, for people coming, coming from up north to you know, switch over to that, to that weather and that environmental mindset of of what happens, you know, and how that feels like to run in those temperatures again.

SPEAKER_01 14:39

Gotcha.

Training For Florida From Up North

SPEAKER_01 14:40

Okay, so these are really really good practical tips and advice for and thoughts as people prepare to potentially hit the registration um or try to secure a bib through a charity, I guess, at this point. But I'm kind of curious in this same vein as to what do you think is the person that this race weekend is really for? Do you because I think you mentioned maybe it's for some folks that are maybe new to Run Disney. Give me some ideas of like if what what personality type or what about the specific runner would this race weekend really be the best curated for?

SPEAKER_00 15:20

Yeah, I think it's I think it's really for a laid-back runner. I mean, you never do Run Disney to PR really anything, you know. Except for your sister who BQ'. Right, except my sister BQing during Dopey. Right, exactly. Um, but, anyways, um, no, I think it is for a laid-back runner. Um, you know, with the emphasis on the food and wine festival, and there's so much else going on, you know, now that the weekend has shifted to uh before Halloween, you obviously have Mickey and Minnie's not so scary Halloween party going on. You have the food and wine festival uh with not just all the food and drink booths, but also the, you know, the bands that are in for eat to the beat and everything. Um, and so it really kind of just becomes this party weekend, you know, then of course capped off by the included uh after party ticket that if you run uh the half marathon or the challenge, uh is included in your race registration. And and so there really is that emphasis of I'm putting in the miles so that I can go have my beer and my cocktails and and all of my delicious food from Epcot afterwards, which is which is a really cool vibe, I think.

SPEAKER_01 16:30

That is a really important portion of this race weekend, I think. And one thing that I will say that I have found in Wine and Tine weekend, time after time, is that we're excited about it when we register for it and maybe even leading up to it, and then we are exhausted come the actual weekend and don't make it to the actual after party. Do you think there are some tips or advice that you would give folks if they do want to go the distance all the way to that celebratory after party? What would you kind of recommend people take into consideration?

SPEAKER_00 17:01

Don't do what, don't do what I did my first year. That uh that is that is really my scoop. So uh uh no, but I think it's important to um, you know, after you finish the half, uh don't go play in the park that day. Save your metal photos for metal Monday, you know. Go back, rest, uh, go to your favorite brunch spot in Disney. I'm personally partial to Olivia's cafe over at Old Key West after my rant runs are done. Um, but you know, you do you, you know, whatever. And um, you know, take it easy, maybe get a little bit of napping, and then get ready to rock out that party when it comes around that evening.

SPEAKER_01 17:40

I think that's the perfect, perfect way of explaining it to folks because yes, I do believe that if you really want to make it to the after party, you're gonna have to plan accordingly. And it may not be a let's keep it rolling. Now, the other race days, I do think there is something to be said about maybe not napping, um, keeping a little bit of movement going so that you're able to go to bed a bit earlier. But that day is the day to go nap and really uh prepare for the festivities. What would you say is the now? I kind of heard you say that like you had your your Epcot where you went to the UK and then decided to go out to the beach club. So are you more team of like I want to do all the different countries with this after party and soak that in? Or do I want to go visit one country, get like a metal photo, get a cocktail, and then kind of skedaddle back? Which which would you say would be the best way that you like to approach it?

SPEAKER_00 18:31

I say, um, you know, I'm one of those really annoying Ron Desi people where I like to be like, oh, I ran by that, I ran by that, I ran by that, you know. So sometimes I'll just like look at like my race photos that I've gotten over the weekend and then during the after party try to go get photos with my medals where, you know, I had photos that photos that came through, you know, during you know, during the races and everything. I think it's kind of fun. It's like, yep, I was here like less than 24 hours ago, and now I'm back with beer and medals. Look at me, I'm so awesome.

SPEAKER_01 19:03

I love that about Ren Disney. I mean, truly, it is amazing. Or, you know, even having that little bit of like you'll go to the just a regular day at Disney and see a character and be like, oh, I've I have my photo with them at three o'clock in the morning. I don't need a photo, I don't need to stay in this line. Okay, let's go back to who this particular race weekend might be ideal for. You mentioned it should be all of Ren Disney essentially has a sense of whimsy and fun. But what if someone is very pace-focused or PR-focused? Do you think that wine and dine still works for them?

SPEAKER_00 19:32

For sorry, I miss that. I missed that lesson.

SPEAKER_01 19:34

If someone is really pace-focused or they really want a PR, do you think that wine and dine could still work for them?

SPEAKER_00 19:39

I think it could. I I do think it could. And I think that really goes back to this is either the beginning or an end of a season for somebody. So so that adrenaline's running and that celebratory

The After Party Without Burning Out

SPEAKER_00 19:50

aspect is there. And I don't know about others, but like when I when I'm feeling on top of the world or excited about you know the beginning of the end or something, my pace is always faster. Um, so I so I think it I think it can be uh be a totally successful uh weekend for somebody. I think it's a great weekend uh if you're gonna try your first um multi-course challenge uh for Run Disney. It doesn't have that um it doesn't, it doesn't have that, I guess I'll say the focus, the pace focus that Marathon weekend brings. Uh it doesn't really bring the faith, trust, and pixie dust as a training plan of Princess, and it doesn't bring the weather of springtime. So I think it's I think it's a really, really great weekend to try out uh you know, you know, try out the challenges for the first time. That would um that's it's a really great time to do that. And the themes, the themes are nearly always impeccable at wine and night, I think.

SPEAKER_01 20:52

I mean they're so much fun because they're usually food related. So how can you go wrong with that? Yeah, absolutely. I love how this particular upcoming year for the two course challenge, it's grumpy because who doesn't get a little grumpy when they're training and they're hangry? Um, so it I think that that always makes it quite, quite fun as well, which is gonna be my next natural progression. If you are going to say that you have only one celebratory drink or cocktail of choice or one celebratory food or snack, what are we going for?

SPEAKER_00 21:24

Ooh, I am going, I'm going for a smoked turkey, uh, which you can find on the uh, you know, kind of the standard resort inside lounge menu at Disney. That's 100% my favorite Disney cocktail. Um, and if that's a celebratory snack, let's think about that. Gotta go with the good old Mickey Bar. You know, it just it brings a smile every time. Right? Yeah, absolutely.

SPEAKER_01 21:51

Okay. So smoked turkey for our cocktail. We're having that with a Mickey bar, maybe not at the same time, but those are our two things. Maybe we're quite at the same time.

SPEAKER_00 22:00

Yeah, that might be a little bit overkill, but okay.

SPEAKER_01 22:03

Well, I I think those are really good um pointing people in the right direction of some deliciousness, no doubt about it. All right, my friend, you really nailed it already with telling us that this is probably the best weekend if you're gonna be trying the challenges. Um, tell me what you think might be the differences in these particular distances. Like what tips would you have for the folks that are going to maybe embark on only the 5K, only the 10K, or only the half for this particular race weekend?

SPEAKER_00 22:29

Yeah, you know, take your time. Um, you know, if you're just starting out with a training program, follow those training programs that that Disney gives you. Um, I would not still be running if I wasn't following the Galloway method. Um, it, you know, it's uh it's the best way to kind of get through those things injury free. And um, you know, I remember when I started even trying to get out there for, you know, two miles seemed like a lot, you know. And now I find myself during training, oh, it's just eight miles today. That's fine, you know. And and it's a real, you know, for someone like me who's like never been athletic at all, um, it's it's a really cool sense of accomplishment. And and if you are out there just running, uh only running one of the races, you know, whether that's you know, that's what you want to focus on, or if it's your first race or running experience ever, never let someone take that accomplishment away from you. I think Disney is the only place where you'll hear someone say, Oh, I'm just running the marathon. I'm just running the half, you know. And and it can it that nobody means to do it, but um, but when you are only doing one, some, and especially if it's your first one, you're like, wow, do I get to celebrate it? Yep, you get to celebrate that because this is all about this is all about you. This isn't about anybody else, it's about getting out there and accomplishing something that's hard. And what's hard is different for everybody, you know. Like, I think I'm gonna try to get to the after party this year, you know. That's hard for me, and that's a way that I can measure success during wine and dime this year. But yeah, just go have fun, you know, and that's really what it's all about.

SPEAKER_01 24:20

I and on that vein, uh, to have the most fun possible. What is the one thing that you think that people should not leave home without? I mean, granted, we know we want to bring our running shoes, but what would you say is a little tip or trick that you've picked up over the Run Disney weekends that you've approached of this is something you don't leave home without it? You like to have it for the race weekends as a uh a token, just in case, or you really rely on it for the entire race weekend?

SPEAKER_00 24:42

Oh, it's a really good question, Christine. Um, let's see. Um, let's see, from a from a practical standpoint, uh I have learned the wisdom of bringing binder clips with me. Um so because because you, you know, sometimes it rains in Florida, it rains when you're in the corrals, and so you know, you know, everyone's like, oh yeah, I'll bring my poncho with me that I can then toss before the rain starts race starts. But if you have a binder clip, you can clip the hood to your hat and then your hat, your head doesn't get soaked too, and that you don't have to worry about the hood blowing off. Brilliant. Yes, so that was like that's like my little practical tip, I think. Um gosh, I don't know.

SPEAKER_01 25:29

I mean, but you you you like you nailed it like about you hit it out of the park with that one because I do think that that is such a good extra tip that or tidbit that we wouldn't necessarily think of. Um, that's so good. And I think let's be honest, friends, if you're gonna do any of the race weekends, if you can only do one race weekend, you should here in Florida plan there may be a little bit of some extra precipitation in the air. And it is good to just be prepared just in case. And that's not something you can easily find when you're actually on property at that point. So that's a good one. Right. Okay.

SPEAKER_00 26:01

Yeah, that's my uh yeah, yeah, that's my practical little tip that I never leave for race weekends without anymore.

SPEAKER_01 26:07

Now we are here, we love everyone, we are not

Smart Packing And Common Mistakes

SPEAKER_01 26:10

here to judge, but what is the one mistake that you see people make during Wine and Dine where you just wish that you could pixie dust them and that they never make that mistake again?

SPEAKER_00 26:19

I think it would be going to the Friday night Mickey and Minnie's not so scary party before the 10K on the summer day. Everyone's gonna do that for the record. Oh, they totally are. They absolutely totally are. Yeah. Um no, you you can always tell the people who have been out at the Halloween party because like they didn't go to bed, right? Yeah, no, you should not. I don't think you should for the record.

SPEAKER_01 26:44

Yeah. If you do decide to do that, I think that the worst you could do is to put yourself to sleep for 35 minutes. I mean, it's 100%.

SPEAKER_00 26:52

No, and that's what you're committed. Yeah, you just gotta stay up that whole time and it could just be a fever dream of a day, you know.

SPEAKER_01 27:00

Yes, yeah, absolutely. Okay. So what's ironic though is that I'm gonna I'm gonna ask now ask you is what would you absolutely suggest that a first timer or somebody who's going to wine and dine do? And I almost wonder if it's gonna be the exact same response, but what is something that you think that everyone should definitely um experience?

SPEAKER_00 27:16

Oh, 100% go to the Friday night Mickey, Mickey's not so scary Halloween party.

SPEAKER_01 27:21

I knew it. I knew it. Bad decisions make for wonderful memories and stories, my friends. I absolutely do. I mean, let's be honest. Okay, decision-making time. I'm gonna just have you finish this sentence. So you've already touched on it, but wine and dine weekend is the right weekend for you if you are new to Run Disney. Okay, perfect. Now wine and dine may not be the right weekend for you if you are chasing your PRs.

SPEAKER_00 27:53

Oh, okay.

SPEAKER_01 27:54

I love how these are like, you know, Allegra's got it down. Allegra's like, I have my responses. I am not gonna even waffle on these. I know exactly what it is. Okay, if someone is choosing between wine and dine princess for their first run Disney weekend, I feel for you it's definitely wine and dine, but maybe why would you say that they should choose one versus the other specifically?

SPEAKER_00 28:13

I think wine and dine is for people who want it for people who really want to get into running as a sport or have maybe had something, you know, something in their brain kind of triggering and be like, oh, this sounds cool, but I'm new, so I just want to try it to see if I like it. Whereas I feel like the focus on princess is more about the characters or the princess aspect of the castle, you know, you know, getting out there because because it is a Disney event as opposed to you, you you know you are running because you're at Disney, you're not at Disney and also gonna run.

SPEAKER_01 28:56

I'm picking up what you're putting down. I think yes, yeah, yeah. There's nothing nothing wrong with what you're saying. Okay, we have to describe white and dine in one word, in only one word. What is the one word? Epic. Oh, that's a good one. Now, now we're we're never gonna be able to get into the Run Disney registration now. Everybody's gonna lock it. Okay, my friend. I can't tell you how much I appreciate your insight, your wisdom, all of the really great um little snapshots. I think I love specifically about what you're saying too is that you gave us a little bit of that Northern Lens perspective because let's be honest, that does influence a lot of people's race day experiences when they come down to any Florida race weekend. So I think that there is a lot of value in that. Any other big takeaways with the most important question of all when we go to Epcot? Where do we start? Canada or Mexico?

SPEAKER_00 29:51

Mexico, Mexico, hands down. If you're doing it the other way, you're just doing it wrong, my friend.

SPEAKER_01 29:57

There, you heard it here from Allegra, my friends. I have my own judgment about that specifically, but that's okay for another time. It's here for Allegra's energy right now. And uh, you did definitely bring the energy. Thank you so much for joining us.

SPEAKER_00 30:10

Absolutely. Thank you so much.

SPEAKER_01 30:13

All right, friends. Allegra gave us such a great look at wine and dine as a first half marathon, a lower pressure Run Disney weekend, and a race that can work really beautifully for runners who are newer to the distance or looking for more fun than finished time stress. But I also wanted to bring in another voice for this episode because wine and dine is not just loved by first timers, it is also beloved by people who have experienced a whole lot of Run Disney magic and still choose this weekend as their favorite. So we're gonna bring on in Wendy Castlevan, who you can find on Instagram at Wendy underscore fun run. Wendy has participated in Marathon Weekend, Princess Weekend, Springtime Surprise, and Wine and Dine because she completed what's called a perfect Run Disney season from Disneyland to Walt Disney World in the 2025 to 2026 season. So when Wendy talks about the different vibes of each weekend, she's not guessing at all. She has lived the early alarms, even with a bit of maybe jet lag included, a lot of heat training, after party energy, and yes, the surprising number of people running in April's. All right, my friends. Well, without further ado,

Wendy’s Perfect Season Planning

SPEAKER_01 31:20

let me bring on in Wendy. Welcome, Wendy. How are you doing today?

SPEAKER_02 31:24

Hi, I'm doing great. It's a beautiful day here.

SPEAKER_01 31:29

So I'm so excited. And I kind of already alluded to a maybe a bit of jet lag that you have experienced because let's be honest, for I feel like you're like a go-to authority. Because if there's anybody who can really speak to all the race weekends after your perfect run Disney season, including Disneyland and a lot of travel, including international, you've done it all.

SPEAKER_02 31:49

Yeah, yeah. I wish that there were more uh like Disneyland Paris. You know, they used to do that. And I missed that whole era, but I have done all the rest of them, yeah.

SPEAKER_01 32:01

Me too. I so wanted that castle to chateau, but I don't know that we'll see that. It's just that's a quick little reminder. We're gonna just interrupt here. A quick little reminder that if something is calling to you, friends in the running world, make it happen because you never know like what the future may hold. But that is actually kind of will lead perfectly into what your current future holds. And that basically you really wanted to approach the Run Disney weekend with a lot of joy. But tell us what made you decide to tackle a perfect run Disney season.

SPEAKER_02 32:30

Yeah, so I actually decided to do that a couple of years ago, that this would be the year. My daughter, it was her first year in college, and so I knew that you know I would be home and no kid in the house, and uh thinking about what I wanted to do, and um and just the opportunity to go ahead and just commit to the entire year. Um, I didn't know at the time that that was gonna be the last year for Disneyland again for a while, but uh but I went ahead and like leaned in and signed up for all the races and had my perfect season, and it was amazing.

SPEAKER_01 33:18

Would you say that it was really important for you to start planning early for it because you had to kind of coordinate for the registrations that we know are can be vastly difficult?

SPEAKER_02 33:29

Yeah, so I had been doing occasional runs, Run Disney runs, and I had always gotten in from the registration. I was fortunate, but I was watching more and more people struggle to get in. And um and so I went ahead and I signed up for Club Run Disney so that I could get the early registration on all of the races. And so by spending that much money, I decided that I'm going to do all of the races then. And so that was my okay.

SPEAKER_01 34:08

So what I'm hearing is that investing in your future self and your goals and your bucket list um was also kind of part of what helped in terms of the accountability portion is kind of what I'm hearing a little bit. You're like, hey, I've already invested enough in Club Run Disney. I'm definitely gonna maximize it by doing all the race weekends.

SPEAKER_02 34:25

Right, exactly. Yeah, I'm not gonna spend a bunch of money and not really follow through. Um, so it was a commitment to time, not just the races, but all the training um to really get myself ready. And for me, the biggest fear was around dopey, as you know. And so uh, you know, thinking like, okay, this will be the year that I commit to running the marathon again and, you know, actually, actually doing that whole crazy thing. Um, so all year, although I did all of the things as a perfect season, that was the one that scared me the most going in. And so I felt like I really needed to commit to all the trainings so that I would have a great season.

SPEAKER_01 35:14

Which I feel like we can officially say that you did, right? I mean, you're here, you completed the season, had a great time. Then, friends, if you um check out her Instagram or if you check out anything that she's posted about these race weekends, you will see there's nothing but absolute joy from weekend to weekend on her face and all of the photos. Um let's take it back a little bit. I do want to get into wine and dine because clearly that's why we're here and why people should choose wine and dine, if that's kind of like what the kind of vibe is for that weekend. But what when did you start getting into running? Give us a little bit about that and why did this kind of naturally kind of add to your bucket list?

SPEAKER_02 35:52

Right. Um, so I started running in 2016. And uh so 10 years ago, I was very out of shape. I had a big corporate job, I had a young child, um, life was very busy, I was not moving ever. And um it was summertime in 2016, so I decided to commit to something that would get me moving. And um, I'd had friends who had done Disneyland races before, and so I um heard that there was a Star Wars race, and I was like, oh, I love Star Wars. Maybe I'll like sign up for a 10K. And I went on the site and the 10K was sold out, but the half marathon was open. And at this time I could run about 10 feet. Um, but I went ahead and signed up for the half marathon, it was six months in advance, knowing that this isn't something I could just show up to. I needed to actually like you know, run regularly in order to be able to finish a half marathon, which I did in January 2017 at Disneyland. So Disney has been a part of my run journey the entire time. Okay, and um, and so it's what got me started. And then uh I had other friends that ran and they kept inviting me to stuff, and so I kept running, and pretty soon I realized I was running all the time. And then during COVID, um, actually a little bit before then, I found Charge running app, which was a a really cool app that um crashed and burned, but it was live coaching, and uh and you'd be running at the same time as people who ran all kinds of different speeds, but um but everybody would be running together, and it was it was great. So I ran with charge all during COVID and uh and kept myself very busy, and I just I never stopped. I've never stopped running. It's part of who I am now, I think.

SPEAKER_01 38:10

I would absolutely say that it's part of your identity at this point. Yeah. Okay, so what I'm hearing, I want to kind of call to this within a span of a decade. You went from somebody who wouldn't have associated themselves as an athlete or a runner, or I actually, in your words, you didn't feel like maybe even really at a higher fitness level to someone who a decade later has done an entire perfect season, including challenge weekends, dopey, marathon, and now 100% this is who you are. Yes. That's incredible. That's incredible. What do you feel? Okay, well, what would you say for somebody who is saying to themselves, I I hear this run Disney World, or I like, I've seen some of the races, I want to do it, but I'm afraid because I'm not a runner. I'm not, I'm just not athletic. I'm not quote unquote fit. What what would you say to them? Like, and what did you say to yourself, maybe if you could go back and and think through as to what what words of encouragement you gave yourself?

SPEAKER_02 39:09

Part of it was about the challenge, you know, just like it was something that I I had not only never done, but like it seemed so ridiculous, you know? So there was this big challenge, and that was exciting. But it was also um Disney, you know, and so it was gonna be about play. And I know from going to Disneyland and doing some events at Disney um uh for work that you know they do things really well, so I knew I would be well supported, and so really it was on me to show up able to actually complete the race, right? Like I I knew it would be slow, I I didn't really

Why Wendy Picks Wine And Dine

SPEAKER_02 40:00

process that I had to hit a time limit. Um, so there's like a 16-minute time limit that you need to make. And going into that half, I mean, I had run nine or 10 miles. I think I'd run 10 miles. Um, so I hadn't run the whole half marathon distance, and my paces were like 1620 or something at the time. And so uh I wasn't certain that I would be able to finish it. You know, I was very insecure about that. I talked my best friend into doing it with me, and she similarly was running about the same speed and was like, yeah, I don't know, we'll see. And we were anxious, and we sat down for dinner the night before the race at a table that had a couple of people who had run the 10k that day, and we were talking to them, and they said, Well, you know, watch out for the balloon ladies, but just stay ahead of them. And if you get swept, like you'll still get your medal, right?

SPEAKER_01 41:09

Things that I didn't know at the time because I just yes, because again, yeah, it wasn't quite as I mean when I first started, I had no clue that there was a balloon lady thing I at all. I just didn't even comprehend it.

SPEAKER_02 41:23

Yeah, so I didn't know about the balloon ladies, right? But um I also didn't know about the time frame, and I didn't know that I would get a medal if I got swept. And actually that was all reassuring. So the night before the race, it was like, okay, well, we'll just do our best. And if we get swept, we get swept. Like, but we'll just do our best. And we did, and we finished, and we never saw the balloon ladies, and it was like a 1440 pace. So it all worked out beautifully.

SPEAKER_01 41:56

I I love that. I love that it kind of reassured you versus creating more anxiety for you, and that you were able to really kind of just be in the moment to enjoy it, which of course now brings us to being in the moment and enjoying more of wine and dine. Of all the race weekends, why is this it? Because I have to be honest, I was surprised. I thought for sure you'd pick Marathon Weekend.

SPEAKER_02 42:17

I know. Well, because Marathon Weekend was the whole season was joyful. I had so much fun at all of the races. And and so, but uh but wine and dine, I love wine and dine. I've done it twice now. I did it last year and then I did it this year. And um and there's a number of things that I really like about it. One of the things is that since it's the first run weekend for Disney World, um it like everyone comes all excited, you know, and like ooh, because there are people who run in all of their, and I'm not the only perfect Disney, and there are lots of people who are live in the area or whatever, and so they do as many of them as they can. Um but this is the first one of the season, so it means nobody's done anything since April at the Disney races, and so the the excitement level is just higher than at any of the other weekends. Um although it doesn't seem quite as crowded.

SPEAKER_01 43:23

Yes, a hundred percent.

SPEAKER_02 43:26

So excitement, but not really overly crowded.

SPEAKER_01 43:30

Yeah, I would say that it's a smaller field than what we see in Marathon weekend and what we see at Princess. Um, it does have, I always describe it as like incoming freshman vibes, like you're excited to see your friends, you are away for summer, you can't like wait to catch up with them. So there's a lot of that kind of energy. Um, so I do feel like it is a really high octane in terms of the energy level and the just like community. Um but you said that was kind of one of the reasons. What are the other reasons?

SPEAKER_02 43:59

So many. Reasons. Um, the themes are all food related.

SPEAKER_01 44:03

Yeah, okay, you can't go wrong with that. Yeah.

SPEAKER_02 44:06

I mean, it goes with wine and dine, but uh but it makes the characters more fun, or they'll choose characters like Ratatouille, or this last year it was um uh Lady in the tramp, you know, so kind of a little bit food-oriented, I don't know, cute. Um, I mean it's the only race that I wore an apron.

unknown 44:31

Okay.

SPEAKER_02 44:31

And I didn't wear an apron this year, I wore it last year, but like you see other people like wearing chefs' hats and you know, um just really leaning into the theme in a in a strange way, you know, like it's it's a little quirkier.

SPEAKER_01 44:49

Maybe it's not like the most common characters, so you get to get a little bit into like the like those deep cuts, those kind of a bit more of that. I agree. I mean, there's like the weather's usually not horrible.

SPEAKER_02 45:01

The weather's not horrible. Um, the race, if you if you sign up for the half, um two things I like about it, three things I like about it, three things I like about the the half. Um, one is that you get the after party tickets, which it's the only race that you get into the parks. And so that's like a perk for me because I'm not a um, you know, like a season pass holder or anything. And so with all of these weekends, I pretty much don't go to the parks. Um because you know, I'm focused on the runs. And so it's kind of it makes it special. Like I get to go to the park and then I get to hang out with all of my runner friends, and um, this last year was it was just so much fun. Um, so the after party is part of the perks, right? But also then the route itself for um wine and dying for the half, it runs through um uh Hollywood Studios as well as Epcot, and and it's just I really liked it. Um it felt like just the right distance, you know, it didn't feel too exhausting. Where even though it's the same distance for, for example, the princess, it's a different route. Like you're running all the way up to um Magic Kingdom and run through the castle, and that's cute and fun and everything, but there's so much time just like running out in the middle of nowhere, you know? And um, and I just I like that you're you're running on the boardwalk, you're running on the uh through the through the both the parks that you know it just it's a better route, I think.

SPEAKER_01 46:54

Okay, so you you've already highlighted two main differences specifically that Wine and Dine has over the other race weekends that people should take into consideration. So if they want the after-party experience, this is pretty much the well, it is the only one that has an official after-party experience at this point. Um, unless if Run Disney brings something else. And then as far as the route, it definitely has a bit more engagement. While a lot of people may feel like they want to hit the castle or Main Street for the other race weekends, there is something special about this one. Um so let's then go point by point. What would you say is the other standout specifically from Wine and Dine that somebody should consider if they can only do one of why this race weekend stands out to you over marathon weekend?

SPEAKER_02 47:40

Um, the weather. Okay. And so this seems strange, but I'm I'm coming from California where the weather is fairly cool but not cold in the winter. And so when I came out to do marathon weekend, it was a lot hotter than it was where I was training, versus the wine and dine weekend, where the hottest part of the year for where I live is September, which means I'm training in the hottest part of the year. And then when I come and it's hot during wine and dine, but not brutal, I'm actually trained appropriately for that weather. Um, not for the humidity, but for for the heat. Gotcha. And so uh so for me that was that was important. Like the weather is actually great. Um, or at least it was for the two years that I came.

SPEAKER_01 48:37

So hopefully that that trend continues. Okay, so the weather stands out in terms of it being um generally a bit milder than the experiences we have during marathon weekend, where it seems to like if you're gonna do all four of those days, you're gonna definitely encounter four very different uh weather days, I feel like every marathon weekend. So that stands out to you. What would you say about wine and dine

Comparing Weekends And Best Distances

SPEAKER_01 49:00

over Princess Weekend?

SPEAKER_02 49:03

Princess is a little bit chaotic. Um there's there's I mean, I love princesses, obviously. Um, I love being able to dress up like a princess. That's super fun. I'm an old lady, so super fun to dress up like a princess. But um, you know, like from from the expo to the races, there's just there's a lot of pushiness, I guess. Yeah, you know, people just very impeach they really want to suck the marrow out of the princess experience or something. And so it makes it less fun. Like if it was the only run that I did, I would think it was a blast. It was amazing, right? Right? It's just that I have the comparison point of wine and dine, which was just laid back and yet still amazing, right?

SPEAKER_01 49:56

Yes, 100%. There is a higher intensity for Princess Weekend, no doubt about it. Okay, and then of course, for the final of the Walt Disney World races, what are the biggest differences that you would say of why wine and dine over springtime surprise? Because those both actually have kind of laid back vibes, right?

SPEAKER_02 50:13

They they're similar in some ways, um, actually in a lot of ways. But springtime is only a 10-miler. Uh, so it it's the challenge is the same because it goes over three days. But um, but the 10 miler is just not as fun as the half marathon. Okay, you're like nearly it's nearly the same route, so it sounds sounds really ridiculous. But the thing is that it's nearly the same route. You put in just as much effort, but you've only gone 10 miles and you haven't gone 13.

SPEAKER_01 50:48

Gotcha. Okay, so you're like, I want my extra 5k worth of character stops, is what I'm hearing you say.

SPEAKER_02 50:53

Right, pretty much. Yeah, I mean, I just I since my first run that I did way back when was a half marathon. There's something different to me about a half marathon versus a shorter distance. Shorter distances, it's not that they don't count, but um, but like I don't know, you know, it's like okay, I did half. Okay, I did a half, okay, I did a half. And then, oh, I only did 10 miles.

SPEAKER_01 51:22

Yeah, I there is that part of like, oh, this is usually a training run for me kind of a thing. But I can't see where that would play into it. Okay. Well, it's also interesting because, friends, for um, as we talk about Wendy, a little deviation again from the Run Disney and Wine and Dine specifically, is that actually talks about like training run distances. Wine and Dun essentially was a training run because two weeks afterwards she did the Every Woman's Marathon, which was also training for Dopey. So, again, you put in a lot of miles where your distances may be a little bit different in terms of like what the perfect difference is, which is why I love having this perspective. So, I'm gonna ask the little rapid fire questions. Like, I want you to finish this sentence.

SPEAKER_02 52:02

Wine and dine is the right weekend for you if wine and dine is the right weekend for you if you just want to go play and have fun the entire weekend. Okay, wine and dine may not be the right weekend for you if wine and dine may not be the right weekend for you if you don't train for it. Uh, because the weather it might be really hot where you are and you might not be training, and it's just not fun to run a half marathon if you haven't trained.

SPEAKER_01 52:36

Oh my gosh, I love that. Can we can we say that the case for all of these, though, friends? Like I know there's a lot of um faith, trust, and pixie dust, and definitely we want you to always bring pixie dust to and you run Disney weekend, but that faith and trust is a whole lot easier to have when you know that you have had the ability to train.

SPEAKER_02 52:55

So yeah, um I just think summertime is like it it kills a lot of people's motivation because it's it can be so hot. And I get that. And so, like, if that's the reality of your life and you're not able to actually do it, like, don't sign up for line in time because your training needs to be during those hot months.

SPEAKER_01 53:16

Right. That's actually one of the first conversations I have with folks when we talk about goal races for the record, is like, what does your life really look like realistically? A lot of other reasons too. Let's say that they don't like they may have perfect weather, but realistically, maybe summer is a difficult time to navigate um vacations or kids being home. So that's a that's a beautiful, really wonderful little tidbit uh takeaway for friends when they're thinking about which run Disney weekend might be the perfect one for them. Okay, if someone can only do one distance, not including the challenge during one and dine, which one would you suggest? I think I know this one for you.

SPEAKER_02 53:52

Well, I mean, I love hats. But the 10K probably. Um and and because it's a perfectly good 10K, yeah. Uh it's the distance is it's enough that you feel like you really ran something, you know, but it's it's not um it's not so hard that it it takes hours, you know.

SPEAKER_01 54:17

It just it's just I agree, neither in training nor in the actual day. Um, so yes, that's a good one. I will caveat that though, that if they want the full wine and dine after party experience that you'd have to purchase. Yeah. Cause it comes with like the after-party ticket is included in your half or your challenge where the 10k you might have to add it on, which again might be worth it.

SPEAKER_02 54:39

You can add it on, you can buy it. But honestly, like the reason it's special is because you just worked your ass off.

SPEAKER_01 54:46

Yes, and you get to go play and enjoy the evening. No doubt about it. Okay, so now what is one thing that you suggest that nobody leave home without um for the wine and dine weekend? Something that they should have packed. They should really consider it as a necessity for the weekend.

SPEAKER_02 55:05

Okay, I'm assuming this is not really obvious things like running shoes and bra.

SPEAKER_01 55:12

Yeah, and even those like running shoes are important. But yes, I'm thinking about maybe like a little tidbit that maybe people wouldn't have thought of.

SPEAKER_02 55:19

Um, okay, well, they definitely would have thought of a costume. And I did not wear a costume in my first couple of Run Disney races, and then I started wearing costumes and I realized I just had more fun. So um maybe aligned to that is something that I started doing uh this season, which is the sparkle tattoos. Oh yes, yeah. Um, and so I put on these like freckles that were sparkles across my my cheeks and um and then later across my um uh from shoulder to shoulder.

SPEAKER_01 55:58

Yeah, like your collarbone area.

SPEAKER_02 56:00

My collarbone, yeah. And um, and it just like it it made me feel so much more playful, you know, and magical. And I only obviously I don't wear sparkles the rest of my life. And so I only wear them for the weeks and races. And it's just like it, it's it's playful. And you want whatever you do, you want your Run Disney weekend to be playful. You want to lean into that, you know, attached to the to the joy of being, you know, alive. And uh, and so whatever it takes for you. For me, it's the stupid wrinkles on my face.

SPEAKER_01 56:43

Okay, you know why I love that one specifically? Because as of this past season, again, knowing that every expo can change, while there is a glitter bar for Princess, you may not be able to easily find glitter on site. Maybe. I mean, there's a couple booths that you may find them, but the little, the little tattoo, the sparkle tattoos are so great because I think that once you put them on, they're pretty much on there. You don't have to worry about them kind of potentially um smearing into your eyes or getting it like any kind of smear, getting it somewhere where you don't want it. So I love that advice. And I love that it's like essentially find your version of this that creates that whimsy and that joy for you, is what I'm hearing you say. Yes. Thank you so much for giving us insight as to wine and dine is such a special weekend. Absolutely. It was super fun.

Final Takeaways And What’s Next

SPEAKER_01 57:34

Friends, I loved hearing these two perspectives together because Allegra and Wendy really show why Wine and Dine has such a loyal fan club. It is not necessarily the weekend I would choose if your only goal is to chase a personal record. It is not the weekend I would choose if you know summer training is going to be the most impossible for your life. And it is definitely not the weekend I would approach with I'll just swing it with faith, trust, and a snack food strategy training plan. But if you're looking for a Run Disney weekend that feels fun, playful, lower pressure, food focused, friend-friendly, and full of the Epcot after dark energy, wine and dine may be your weekend. I also think this episode gives us a really important reminder. The best Run Disney weekend is not universal. It depends on your season of life, your training environment, your travel budget, your tolerance for humidity, your love of costumes, and whether or not you realistically want to be awake early enough to run and then awake late enough to party. I think you have to do that though if you're going to do it. That is a very specific form of endurance, my friends, and one that we can talk about because it really does include some training. So as we continue this four-part guide, I want you to keep asking yourself a better question than which weekend is the most popular. Ask instead, which weekend actually fits me, which one fits my goals, which one fits my schedule, my energy, and which one gives me the kind of experience I really want to have. Because yes, Run Disney is magical, but it is still real running, real training, real travel, and real money. The more honest you are about what you want from the weekend, the more likely you are to choose the race that gives you a finish line, a feeling you came for. Next up in this guide, we're gonna continue breaking down the Walt Disney World race weekend so you can decide which one belongs on your calendar, your future wish list, or maybe your charity bib search. And if Wine and Dine is already calling your name, take that as your sign to start thinking ahead. Future you may want a costume, a training plan, hydration strategy, and possibly a binder clip. Allegra would be proud. Until next time, keep chasing the miles that bring you joy, keep making room for a little magic, and keep taking those extraordinary strides.