Is a surprise trip a good idea, or a disaster waiting to happen?

Have you ever dreamed of pulling off the ultimate surprise vacation for your kids or spouse? It sounds picture-perfect in theory, but in reality, it can just as easily turn into a logistical nightmare or an airport meltdown!

In this episode of Talk Travel to Me, host Kristy Ouellette sits down with Mickey Guru Travel Advisor Nicole Fresia to unpack the ultimate question: Is a surprise trip a good idea, or a disaster waiting to happen?

Nicole and Kristy share hilarious personal stories—including a childhood "Texas decoy" trip that required a flight attendant intervention, and a Six Flags bait-and-switch that resulted in some unexpected childhood whining. They also dive into the heavy operational logistics of keeping a secret under your own roof.

What We Unpack in This Episode:

• The Personality Test: How to determine if the person you are surprising actually wants to be surprised (planners vs. go-with-the-flow travelers).
• Logistical Landmines: The secret art of updating passports, securing corporate PTO, and managing packing without getting caught.
• The Decoy Dilemma: Why your "fake" destination needs to be carefully calibrated so your family doesn't end up disappointed when the real plan is revealed.
• Behind-the-Scenes Rescue: A real-world look at how a travel advisor saved a surprise anniversary trip for 25 people in Aruba when mass flight delays struck.

Whether you're looking to surprise your spouse with a romantic cruise or want to plan a magical Disney reveal for your kids, this episode gives you the exact framework to execute it flawlessly.

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🎙️ Hosted by Kristy Ouellette
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Transcript

[00:01] Intro: Ready for your fast pass to the perfect vacation?  This is Talk Travel To Me.  Join host Kristy Ouellette and the Mickey Guru team for one big travel question every episode.  Solo insights or expert round tables all with a sprinkle of magic and the ultimate insider edge.  Fasten your seatbelt, it's time to talk travel.

[00:26] Kristy: Hey traveler, welcome back to Talk Travel To Me.  I'm your host Kristy Ouellette and this week we're answering the question, is a surprise trip a good idea or a disaster waiting to happen?  I'm joined by one of our fabulous Mickey Guru travel advisors, Nicole, for this episode.  Nicole actually pitched the idea and since she's planned more than her fair share of surprise trips, we're going to answer this together.  Welcome, Nicole.

[00:53] Nicole: Hi there, I'm Nicole and I'm from New Hampshire.  I have been on the receiving end and the planning end of some surprise trips and boy, do I have some lessons to share.

[01:05] Kristy: Oh, I can't wait.  So tell us about the one that you received because that feels much more exciting than planning maybe.

[01:14] Nicole: Yes, it was.  I was, I don't know, like sixth grade.  My parents told us.  we were going on a trip to Texas to see one of my mother's many, many cousins.  And I was like, cool, I don't know who this lady is.  Awesome, we're leaving.  And we were in the airport and they said, now boarding Orlando.  And I looked at my parents and I was like, oh, and they're like, shh, because I have two younger sisters.  And so they decided on the plane, let's tell the other two so that they're prepared when we land.  Well, my middle sister, she's going to kill me for telling this, but my middle sister got so mad.  She was furious.  She's like, stop lying to me.  We're not going to Orlando.  We're not going to Disney.  We got the flight attendant involved and she tried to tell her, she's like, my parents paid you to lie to me.  That's not nice.  It wasn't until we actually got to Disney that she believed us and was like, oh, so it's a really great story.  I don't know how my mom hid all of the Disney gear that she was like packing for us.  We had no idea.  We saw her packing.  No idea.  But yeah, it's one of those stories that like we talk about all the time.

[02:30] Kristy: Oh, my gosh, that's so cute.  We did.  I planned on with Allison when she was younger with her best friend and her best friend's mom.  And we told them we were going to go to Six Flags in the morning.  So the girls slept here and Christine, the little girl's mom, came over in the morning and we woke them up together and we were like, hey, guys, we're not going to Six Flags.  And they were like, what?  Like they were like, and I think they were probably like nine or ten, maybe eleven, but that that range.  And they instantly both started whining at us because they really want to go to Six Flags.  And like we were like, we thought we'd go to Disney instead.  And they both like snapped awake.  But I think my favorite part of that whole thing was that whole first day they kept looking at us and going, is this real?  Because they wanted to do Disney together so badly.  They were both only children and they've never done it with like another kid like that before.

[03:29] Nicole: So it was both of their first trips to Disney or they've been multiple times.

[03:34] Kristy: They've been multiple times.  They were like a once a year family.  We were.  But yeah, it was like they never had been with another child before.  So that was like so cool.  And they were old enough that we felt comfortable letting them to go do things on their own, but they didn't want to.  We kept like sending them in the same park.  But I remember specifically we were sitting outside of oh my goodness, what's the name of the restaurant that I don't like?  Brown Derby, Hollywood Brown Derby.  We were sitting outside there and we had a pretzel and a drink and we were like, guys, just go, go.  And they were like terrified to go too far.  So we were like, OK, they did warm up a little bit, but that was one of those things we had in our head that they were going to do on their own.  Some of these things.  And we could kind of relax a little because, you know, you have an only child, too.  You're like they're everything.  And so like the idea, OK, here.  we'll we'll we'll bring a friend with you.  It didn't work out that way, but they were very appreciative and they loved it.

[04:35] Nicole: But that's still special, though, that they wanted to spend all that time with you in Disney, even with like their friend.  They're like, no, my mom's here.  I want to be here, too.

[04:43] Kristy: Yes.  Yes, exactly.  Exactly.  It was great.  So when you have a client reach out to you and say, hey, I want to surprise my kids or my spouse.  What is the first thing that goes through your mind?

[04:58] Nicole: Well, is this really a good idea?  There are so many ways that a surprise trip can go wrong.  And I try and talk to them about, OK, let's talk about who you're trying to surprise.  Do they appreciate surprises?  Because there are people who like to give surprises and they're not liking the receiving end of it.  Yeah.  But not just that.  It's like, who are you going with?  Are they going to keep the surprise or are you going out of the country and you need to update your passports?  How are you going to do that secretively?  I have I. recently planned a trip.  It was really sweet.  It was the husband's birthday.  So she planned a surprise cruise and it was their first time on a cruise.  I'm not really sure how she got an updated passport without him realizing what was going on.  Yeah.  But she did.  And then a surprise him on his birthday.  And then they left four days later.  So there was like zero time to prep and he was like, what?  Where we're leaving out.

[06:08] Kristy: Yeah.

[06:10] Nicole: So that one worked out.  I had another one where some family was trying to surprise a kid and go to Disney.  And they're not like a huge Disney family, but they are like, wow, they've never been on this trip before.  This is going to be so exciting.  And they were all so let down when they gave the secret up and the kid was like, OK, because the kid just didn't understand what was happening.  But all this built up anxiety and like excitement in them.  And they're like, oh, all that hard work with you for nothing.  So I try and talk to them like really what is best for the person you're trying to?  surprise.

[06:54] Kristy: Well, that brings up a really good point, right?  If you don't know, if you're a kid and you don't really know what Disney is or why you would be excited about it, that's going to fall flat almost for sure, because they don't get it.  Whereas if you've had a kid that's aware of Disney asking to go to Disney, like all of that, then they'll be excited.  But Disney is one of those places, especially.  that is overwhelming for sure.  And I think a lot of kids don't really know what to expect or what they're getting into.  And so then they're just kind of like, OK.  Yep.  Yeah.

[07:28] Nicole: But the overwhelming piece is another thing I wanted to bring up, because I had two trips that I planned for kids who had been to Disney previously and their grandparents were surprising them.  The first kid was a little bit younger.  It was only second, third trip, maybe.  And he was just so overwhelmed by all the wonderfulness of Disney that when the grandparents showed up, he was like, oh, hey, and like went on ignoring them because there was other things to see.  And it was.  like a really big deal for them to be there.  So you could see a little bit of hurt in their faces.

[08:08] Kristy: Yeah.

[08:09] Nicole: But then on the other hand, I had this client whose grandparents showed up and it was a bigger hotel than they're used to, like more of the deluxe feel.  So she already felt spoiled.  And then she was like, why are we waiting around, Mom?  Let's go.  And then in walked the grandparents.  And oh, my gosh, when they sent me the video of that, I was like tearing up because it was like that picture.  Perfect surprise moment, like running to their arms.  It was so wonderful.

[08:40] Kristy: I love that.  And I think like we did a surprise trip with my nephews because they had never been.  And my goodness, I'll have to find the video because it exists on YouTube.  And they my sister and her and her husband did it in a couple of different ways.  First, they were playing a lot of videos Disney related at home to like getting them kind of like.  And then on Christmas morning, they created a video that they played on the TV.  So it said.  and the and the older one was reading, but just barely.  And the little one was definitely not.  So on the TV, it said, like, open your present.  And they opened the box and the balloons came out with Mickey and stuff.  And it was so cute.  But it was the older one got it first.  And he was like doing a little shimmy dance and the little one started like to dance.  and like he didn't know why he was dancing.  Like he just saw that the older guy was excited and then his eyes like lit up and he went, wait, are talking cars real?  Because like there was a picture up on the screen of that of lightning.  And so they did all of that in the morning when it was just the four of them at home.  But when we all came over later, we all opened cards that said we were going to Disney with them.  Oh, I love that.  Oh, my God.  I'm still getting goosebumps.  And these guys are.  they're like graduate from high school and, you know, old now.  But like we were like, wait, we get to go with you.  And.  then they realized that Allison, their cousin was going and it was like such a moment.  And I thought that and we left.  that was December.  We went in mid-January.  It gave them time to be excited and in on the surprise versus being thrust at them, which I felt like made a huge difference because they were given time to the surprise.  They were given time to then get excited.

[10:28] Nicole: Yes.

[10:29] Kristy: Along the way.

[10:30] Nicole: Yes.  That that piece of time in between when they find out and when you actually go, I think plays a huge part in the reaction and the enjoyment of the whole thing.  I did plan a trip for 25 people.

[10:50] Kristy: I remember.

[10:51] Nicole: Yeah, it was it was really great experience.  But there were some moments I was like, well, this is was a little dicey.  Basically, the life was turning a certain age and it was also right around their anniversary.  So the husband said, let's go for our anniversary trip.  That's where we went on our honeymoon.  So she's thinking all this romance all the time like they're together.  And then in walk 23 other people, all of whom they love and they.  are great at hosting people.  So it worked out in that sense.  But there was a couple moments I was like, man, if that was me, I'd be a little sad that I wasn't getting that one on one time with my husband.

[11:34] Kristy: Yeah, that's a really good.  I good thought is whatever you are decoy is.  the idea of having a romantic escape with your husband is a great one.  So then it turning into a friend trip could be.  Yeah.  OK, pause.  I need you to think of someone in your life right now, a friend, a sister, a coworker, that one person in your group chat who plans every trip and takes it very seriously.  Got them?  Good.  I need you to send them this episode.  Not later.  Now.  Well, wait, wait until we're done.  When you're not done listening, then you could do it.  But soon.  Word of mouth is how little podcasts like this one grow.  And I would love nothing more than to be the show that your whole travel squad is listening to.  So if talk travels me has ever saved you from a bad hotel, helped you survive a theme park or?  just made your commute a little more fun.  Pass it on.  Your people will thank you.

[12:26] Nicole: Probably.

[12:27] Kristy: I mean, I can't guarantee it, but I feel pretty good about it.  OK, back to the good stuff.

[12:33] Nicole: It definitely works for this group like they are.  They're really great at hosting live parties like they love that.  Yeah, that is definitely their persona.  So it worked out.  But like I remember feeling like, well, I hope she's OK with this.  But like on the flip side, she is trying to do a surprise trip for her husband's birthday because he's not reaching that same age.  And he kind of got wind of it like not super.  But he's like, if this is what you're doing, stop.  I do not want a surprise trip.  Oh, because he is like he's the planner.  He's the one who needs to be in control of everything.  And he did not want that surprise.

[13:14] Kristy: Gotcha.

[13:15] Nicole: So it was interesting.

[13:17] Kristy: Would you like a surprise trip?  Like if you're hoping?  No, really.

[13:22] Nicole: I'm not a surprise person at all.  OK.  I am a travel advisor for a reason.  I like the planning aspect.  Yeah.  The in the.  moment was easier.  before I was a mom.  Sure.  Now it's like there's way too many things that need to be taken care of.  And I love my husband.  He is fantastic.  And he is pretty spot on with things.  But oftentimes that's with like a little bit of coaching from you.  Like, hey, do I think about this yet?

[13:52] Kristy: Yeah.

[13:53] Nicole: So that would stress me out.  Would you want a surprise trip?

[13:57] Kristy: I would actually.  And I have told my husband for years and I literally am like, you know, a few travel advisors, like, yes, I am one.  But I, you know, a lot of really great ones.  Somebody can help you because I am the one that carries all of that mental load.  I think you touched on an important difference, though.  My child is an adult now.  If I was worried about a preschooler or young elementary schooler, I don't know if I would have wanted it then because of I am very particular or was very particular about what I wanted for her and the idea of me just disappearing.  Now, she's going with us.  Bring it on.  But the idea of him now doing.  something like that would make me so happy, like over the moon.  And I don't even care where it is.  Like, I don't I would go on a cruise.  I would go to Disney World and anywhere.  The only thing I don't want to go to an air because he is our editor of this podcast.  I do not want to go to Machu Picchu.  I know lots of people do, but that is not a place I'm interested in visiting.  So nothing no shade to it, but I'm just not that adventurous.  I'm like, bring me on a cruise.

[15:06] Nicole: You like to relax.

[15:07] Kristy: Yeah, exactly.  But I would love for him to take the reins like that and go do it.

[15:14] Nicole: Eric, this is your notice.  We're going to plan this trip for Christie.

[15:18] Kristy: Exactly.  And I will say that in his defense, when we talk about this, he says to me, OK, but you'd have to stop planning your own trips in order for me to do that.  And I'm like, oh, well, I don't know, because I do surprise him time to time.  Like, oh, I'm doing a California Coast cruise with my sister.  What if he?  planned something that exact same time?  So it would be a challenge, but he's up for it.

[15:41] Nicole: Would you want other people on the trip with you or would you want it to just be you and Eric?

[15:47] Kristy: Oh, that's a good question.  I like both.  I'd be perfectly fine if it was just the two of us.  But we've also done with especially other travel agents from our company or from my colleagues that own other travel agencies.  We've traveled with them before.  I love going with couples.  And just because to me, it's like you have your own time and time together.  Yeah.  So like that, the mix is fine.  But yeah, I'm open to that.

[16:16] Nicole: Anyway, I have some ideas.  Eric will definitely talk.

[16:21] Kristy: Have you ever seen other than the person you were talking about now a few minutes ago that said like, nope, stop, I don't I don't want that.  Anybody that has actually gone on the trip and thought, no, I don't want to ever do that again.  Have you gotten that kind of feedback?

[16:38] Nicole: No.  But that's because when I was talking to the person who approached me and they're talking about surprising.  this person and I was like, oh, I'm going to do this.  And I was like, okay, tell me a little bit more about them.  What do you guys like to do?  And I started getting the sense a surprise might not be the best bet.  So we had a real honest conversation.  And this lady was like, you're probably right.  But I want to give him a surprise.  And I was like, okay, let's talk about all the ways that this could go sideways.  You don't want to start your trip off fighting.

[17:11] Kristy: Sure.

[17:13] Nicole: What happens if he has something planned that he didn't tell you about?  You know, it's one thing if I have a relationship with both people and I know them and I can kind of like suss out the situation like, oh, what are you up to this week or whatever?  Yeah.  But when it's a client that I don't really know, I can't do that.  So I can't help them facilitate, make sure that time frame is open.  So ultimately, after talking, she's like, okay, I will talk to him and make sure he's on board.  And he was.  But she she kind of.  said, like, you're probably right.  The surprise was more for me than it was for him.  Yeah.

[17:52] Kristy: Yeah.  And that I think it's important to have those conversations because I think our our clients especially can get really excited about their own idea.  But that's another way that we help them.  It's not that saying like we're not going to do the trip.  Right.  You want to book the trip?  We'll book the trip.  But you gave them that crucial advice of like, do you want to start fighting?  Like if you're like, hey, wake up, we're going to the airport and they don't want to go to the airport.  Is that how you want to start this experience?  I actually have a consultation with somebody coming up this coming Friday.  So I will have already had it by the time this airs.  But the person is has a big milestone birthday and they want to do a trip.  And in the notes that she sent me, she talked about a river cruise, an Alaskan cruise or a Mississippi River cruise.  And I thought to myself as I read it, oh, my God, like we really are all over the place.  We know we want a ship involved.  So much right.  Right.  Part of my questioning is going to be like, where are these ideas coming from and figure out like what that looks like?  And I can already tell based on the little bit of notes that I had that we might have that same need to like, what if you said I'm planning something for your birthday?  And this is the time frame.  I'm thinking, are you cool with that?  You don't have to tell them the specifics, right?  You could.  just I'm planning something and asking, would you like to bring friends and family on or bring because that might give it away.  But would you like it to be just us or would you like to include other people?  And who might those people be?  Like having those questions might be good for them to kind of have that initial conversation.

[19:34] Nicole: But it also gives them the time to check and make sure they can get the PTO off.

[19:40] Kristy: Yeah.

[19:42] Nicole: Before I started being a travel advisor, I actually helped plan my husband's bachelor party a little bit.  Our friends were really great.  They knew what.  they wanted to do.  They're like, how do we make this happen?  It's like, OK, I got you guys.  So I reached out to my husband's boss and was like, Hi, I know you have some family things going on this weekend, but can my husband take this extended time off for his bachelor party?  We were really lucky because one of the groomsmen was my husband's boss's son.  So like there was a connection there.  And she's like, Yeah, I had a feeling it was coming.  Totally fine.  Make it work.  But if I didn't know her or the other guys didn't know her, like that could have been really awkward.  to be like, they literally scared him outside and threw him in the trunk of a car to take him away.  Oh, my God.  Or for a different time.  But like, can you imagine him be like, I'm in the trunk of a car.  I'm not coming to work today.

[20:42] Kristy: Yeah.  And the worry that you'd have.  Right.  Like, and I feel like that's that might be why you might want to.  if you don't have a connection like that, you might want to give them advance notice, not necessarily what you're doing.  But like, hey, I need you to get these four days off of work coming up soon and seeing if that helps.  Because that's a big thing.  And I know that not everybody is going to want someone else talking to their bosses.  And you have to know your people.  Right.  So like that, that's a consideration for sure.  Interesting.  I think there's a lot of like those ways that it can be done.  I do think and I'm sure you agree with this, but having a travel agent to help you facilitate so that you can keep as much of it out of your house as possible makes a whole lot of sense.

[21:36] Nicole: That Aruba.  Oh, go ahead.

[21:37] Kristy: Oh, no, go ahead.

[21:38] Nicole: I think I'm going to go with the Aruba trip because the couple was already down there and they were flying when all the flights were getting delayed and canceled.  Well, there's people from three other states coming to see them.  And there was a trance like a big bus that we rented to get them all there.  Well, all of a sudden, everyone's flights were all over the place.  Oh, yeah.  Can you imagine if I wasn't involved?  Yeah.  I was able to get on the phone, redirect all the transfers, reach out to some people who weren't flying, be like, OK, this is what's going to happen.  You need to go here.  You need to get these people because their phones are off and I can't get a hold of them.  So there was a lot of that behind the scenes going on.  But otherwise, he would have been on the phone all morning ruining the surprise for his wife.  And that's not a fun way to start your vacation.

[22:28] Kristy: Yeah, no.  And I love that because that is a lot of what we do in the background when things go awry.  Right.  Like people say all the time, like, I can book my own trip.  Yeah, sure, you can.  But are you ready and prepared to deal with all of those things that can happen?  And certainly not.  They want to be enjoying each other in Aruba before everybody shows up and surprises them.  So for sure.  All right.  So we think it is a good idea then or a disaster.  What do we could be both?

[22:57] Nicole: I'm going.  to say I err on the side of caution here, unless you know your person is like in love with surprises and that is their thing.  Don't don't surprise like the day of we're leaving.  Give them maybe some advance notice.

[23:13] Kristy: Yeah, yeah, I agree.  I think it can be a beautiful experience and make people feel very taken care of and seen if that is their love language, so to speak.  Right.  But I do think that the idea maybe that I'll plan a big expensive trip and surprise my husband so that he won't ask me about the budget of a trip might be that could be a way to go.

[23:37] Nicole: Yes, love that.  Yeah.

[23:39] Kristy: Awesome.  Well, thank you so much, Nicole.  And that is one more question unpacked.  Next week's question is still up in the air, but I'm sure you're going to love it.  So make sure you're subscribed so you don't miss out.  If today's episode got your thinking, feel free to reach out to Nicole or myself.  You'll find us both at Mickey Guru dot com and we would love to help you plan your next surprise or even well announced vacation.  See you.  real soon, traveler.

[24:09] Outro: Thanks for listening to talk travel to me.  We hope this episode cracked open inspiration for the treasures that await you at your next dream destination.  If you love the show, please review, subscribe and share it with a friend at Mickey Guru Travel Company.  Where your trusted guides for theme parks, cruises, resorts and more.  Visit our website at Mickey Guru dot com to learn more and book your vacation today.