The Questions Every Traveler Asks (And What We Actually Tell Them

Every Client Asks. Here's What We Actually Say.
Whether it's a first-time Disney family, a couple planning a honeymoon, or someone who's never considered a cruise, Ryan and Julie hear the same core questions over and over. This week, they decided to just answer them — all at once, on the podcast. No sales pitch, no runaround. Just the real answers they give clients every day, including the ones that are a little more complicated than they first appear. If you've ever wondered whether a travel advisor is actually worth it, this episode is a pretty good place to start.

Is It Really Cheaper to Book Online?
Ryan and Julie tackle the most common question they hear: can't I just do this myself for less? The honest answer is sometimes yes — but the real question is what you're giving up when you do. Mental load, time, and the risk of booking the wrong thing at the wrong price top the list. They share how a travel advisor's job isn't just to find a price, it's to make sure what you're booking is actually right for you — including knowing which beach is covered in seaweed in August.

Travel Insurance: What's Covered and Do You Actually Need It?
This one comes down to risk tolerance, not whether you plan to take the trip. Ryan and Julie break down typical coverage categories — cancellation, medical, evacuation, baggage, and delays — and explain that policies vary widely, which is exactly why they vet specific companies for clients. A vivid example: a client group that skipped insurance and got caught in a hurricane two days before departure. Plan for about 5% of your total trip cost as a starting benchmark.

Is That Destination Safe Right Now?
Social media and the news cycle make this question louder than ever — but louder doesn't always mean more accurate. Ryan and Julie explain how they respond: State Department advisories, on-the-ground partners, and some honest perspective. A Cancun safety incident that happened the distance of LA to Chicago from the resort zone is not the same as a threat to your resort. Context matters.

What's the Best Resort or Cruise for My Family?
Short answer: it depends, and that's exactly why this question deserves a real conversation. Ryan and Julie walk through how they match families to the right fit — and why a top-10 list from a travel magazine (often sponsored or years out of date) is not the same as advice from someone who's been there and booked it before.

How Far in Advance Should I Plan a Big Trip?
For milestone trips — honeymoons, multi-gen family travel, graduation trips — the answer is: reach out as soon as you know you want to go, even if it's two years out. Julie is already mapping an Italy graduation trip for next year that she's been quietly tracking for twelve months. For popular destinations like Turks and Caicos or Disney around the holidays, availability goes fast. Standard trips in the four-to-six month range are usually still workable.

Bonus Question: The One They Always Get at Disney Consultations
Julie's add: nearly every first Disney call turns immediately to dining reservations and Lightning Lanes — months before it's time to think about either. Her advice: book the room first, then let the timeline guide you.

Where in the World? 
Ryan shares the story of a mother-daughter graduation trip to Walt Disney World — an upgrade to Animal Kingdom Lodge that ended with a giraffe outside their window on arrival. No savannah-view room required.

Next week: Ryan recaps the Las Vegas and Mighty Five National Parks leg of his Canyon Spirit Southwest trip. Start planning your own adventure at wonderandbeyondtravel.com.

Transcript

Ryan 0:00

Hello and welcome to All Things Travel. As travel advisors, Julie and I work with all sorts of clients, but often get the same types of questions regardless. Today, we're discussing your top questions for us as travel advisors

Julie 0:13

tune in with travel advisors Ryan and Julie. He is your travel professor teaching you everything you need to know to have a magical vacation, and I'm a Disney-loving Maryland mom of three and a specialist in family travel. And together we are the co-owners of Wonder and Beyond Travel. Whether we're discussing incredible destinations, top vacation tips, or sharing personal stories, it's always all things travel

Ryan 0:40

Well, Julie, this is a week of catch-up for me. I just got back from my big old Southwest US trip and, yeah, tried to hit the ground running once I got back. it took a couple days to shake the dust off, but I'm back into it now. I'm excited. The next couple episodes after this are gonna be about our time in Vegas, our time with The Mighty Five National Parks, and, then aboard Canyon Spirit, so I've still very much got that on my brain. I sent out a newsletter to clients about that today. I've been posting about it, so it's, you know, it's there. But, yeah, how are you doing?

Julie 1:16

We are good. We have, we've had a busy week. We've got a busy week coming up. We're doing fun Maryland things this weekend, like having crabs. I don't know if you've ever picked a crab before.

Ryan 1:27

I've eaten a crab before. I didn't know I had to pick it beforehand

Julie 1:31

Well, you can't just, like, eat the shell. You have to, like, open it up and get the

Ryan 1:36

Oh, is, is pi- is picking what you're ta- is that opening the shell?

Julie 1:40

Yeah, it's like opening the shell,

Ryan 1:42

Oh, I thought you meant like picking one out

Julie 1:45

Yes, that one please.

Ryan 1:47

Yeah. Well, that's what I figured. you bring them out and the kids would get all excited, and they name them and, they make up stories about them, and then you cook them, and then halfway through the meal you tell them that they're eating their new friends that they've named

Julie 1:58

No, and trust me, they're not eating on, they're having like hot dogs probably.

Ryan 2:01

Wow

Julie 2:02

it's a very Maryland thing, especially in the summer, so we are pumped.

Ryan 2:07

All right, you pick away

Julie 2:09

to today's episode

Ryan 2:11

So we put this together because we really thought about what are the main questions that we get all the time? and as I was thinking about this, there's some real value in kind of talking through some of these with our listeners that probably know why they should work with us or what value we might add to their trip. But just to give some more idea about, how they can be better consumers and how we can best help them. But before we get into those questions, Julie, I wanna remind folks, if they did not listen to last week's episode, we broke down this question of who is a cruise for? Okay, so the first question, Julie, is, "Isn't it cheaper to just book myself online?" This is a question we get a lot, and rightfully so. I totally get it. Isn't it cheaper for me just to do it? What if I find this price? Should I go ahead? there's a lot of misunderstanding or assumption when it comes to this type of question, right?

Julie 3:13

Yeah, and there's a lot of ways to answer this question. So first and foremost, like honestly, yes, sometimes it might be cheaper for you to book online. Sometimes. But other times it's going to be the exact same price or potentially cheaper with us, and I, I really hate the word cheaper, so maybe like more affordable.

Ryan 3:38

Yeah. I mean, if you think about, if you're spending thousands of dollars on vacation, is cheaper really the word that you want to use?

Julie 3:45

I don't like cheaper. So here's the thing. If it is the same price or maybe a little bit less when you are looking at it yourself, consider what you're missing when you book that yourself. is your time valuable? Is your, you know, your mental load of that trip valuable to you? Are those things important to you? Because if they are, then you need to work with an advisor. If you are anxious about taking your kids to Disney World for the first time and feeling overwhelmed about dining and Lightning Lanes, do you wanna spend your next couple of months researching all of that and watching a ton of videos and Googling and being, overwhelmed by Facebook groups? I mean, probably not. same thing with an all-inclusive or, cruises

Ryan 4:36

Going to Europe for the first time

Julie 4:38

Absolutely. We, have resources for every single one of those things, our role is to take that mental load off of you. And I know as a mom, I've got way too much mental load as it is. if I was not skilled in travel, I would not wanna be planning a trip to Europe for my family

Ryan 4:58

And I think for me, when I think about this question, it's are you sure you know what you're booking? we talk about this a lot. the price that you see online, the pop-up, where it leads you down a rabbit hole, oftentimes is not really what you want. you're booking something that has a non-refundable deposit, or you're booking something that is not in the category that you're really, thinking about. Or you're booking the ship or the resort that you saw on TV, and that in no way is the right thing for your family. the number of people that think Viking is the only river cruise company out there, that type of stuff. and so I would say not necessarily focusing on is it cheaper. And yes, by the way, we can find you perks. We can add to your vacation. We can find cheaper rates a lot of the times. But really, when it's talking about is it cheaper to book yourself, it's about do you have the right value in what you're looking for when it comes to a vacation?

Julie 6:00

Yeah, multiple times this came up, just throwing another example out there. A lot of all-inclusive vacations that I've been working on lately, and, I will throw out my options, my suggestions, and sometimes I will get a response of about this resort? Have you worked with this resort before?" And I'll say, "Yeah, absolutely. I do know that resort. I think it's a good resort. I don't think it's a good resort for when you want to go because the beach is going to be covered in seaweed." And they're like, "Oh yeah, definitely not." But had you just said, "Oh, I've heard of this. Let me go ahead and book this for my trip," and then you'd get there, that beach picture is not at all what you're gonna see

Ryan 6:38

Question number two, what's included in travel insurance and do I actually need it? Another loaded question, right?

Julie 6:47

Okay, so to know what's included in your travel insurance, we have to read the fine print because they're all different.

Ryan 6:53

They're all different.

Julie 6:54

Oh,

Ryan 6:54

that's why we tend to just suggest several companies, because we know what's included and we've worked with them before. usually there's cancellation or trip interruption, there's medical and emergency evacuation, there's baggage coverage or personal item coverage, and then there's coverage for, delay in your trip. And again, it's different if you want all of those things, if you just want medical. let's say that you are comfortable with the trip cost, but you wanna have medical coverage, we can provide that separately. the do I actually need it part is really your risk tolerance, and not just are you going on the vacation. I hate that when I hear that. "Well, I know I'm going on the vacation, so I don't need trip pr-" It has nothing to do with the fact if you are going on the trip or not. It has everything to do with the fact of what's gonna happen once you hurt yourself right before the trip or after the trip. We had a guy on our, Mighty Five tour that then got on the train with us. He had had shoulder surgery the week before, and he was in a lot of discomfort throughout this whole trip. And my guess is if they... I, I don't, I didn't talk to them specifically, but my guess is if they had travel protection, they would not be on that trip.

Julie 8:18

You

Ryan 8:18

he looked,

Julie 8:19

protection?"

Ryan 8:19

he looked pretty miserable. And again, that has nothing to do with are they going on the trip or not. That's just the happenstance of life

Julie 8:29

Right. It's like do you not get house insurance because you're like, "Well, I'm gonna live in the house no matter what?"

Ryan 8:36

Yeah

Julie 8:37

there are so many examples we could throw out there of a time that our clients had travel, either had travel insurance and needed to use it or didn't have travel insurance and needed to use it. One that, goes directly with what you said about, like, I'm going anyways, I had a multi-gen big family trip going to Disney in October or September a couple of years ago, and a hurricane got named two days before they were gonna leave, and they did not have insurance. And I was in Hawaii, they're calling me at 6:00 in the morning like, do we do?" And then they were upset with me because it was going to cost to move their trip.

Ryan 9:18

Yeah

Julie 9:18

"Well, you opted out of insurance." And they're like, "Well this..." You know, they were very upset about it. again, obviously you're gonna go except when a hurricane comes,

Ryan 9:26

how much is travel insurance? It really depends where you're going. It depends on your age. It depends the type of coverage that you want. For instance, if you want cancel for any reason, there's often a time limit to book that. There's often a cost associated with adding that on. But you can really kind of average in about 5% of your trip costs would be your coverage for, travel protection. All right, Julie, the third one, is destination blank safe right now?

Julie 9:59

I feel like with the way social media is, the way the news cycle is, there is always something coming up where someone will say, "I have this trip booked here and now I'm worried," or, "I heard about this," where maybe these destinations, their safety level hasn't changed. You're just hearing more about things.

Ryan 10:19

Yeah

Julie 10:20

I try to turn that a little bit. You know, we don't give legal advice. We absolutely do not say you will be 100% safe. What we do is we give you the facts of what the State Department advisory is and what our on-the-ground partners are saying about the destinations. but I do try to tie it back to, like, okay, well, what happens in our local city

Ryan 10:42

Right.

Julie 10:43

maybe nothing happens, but good chance that something did happen.

Ryan 10:47

Yeah, and I think some of it is... in no way are we trying to minimize things that happen to people on vacation or real incidents. not that way at all. But I do think i- if you've been in this business long enough, right around spring break, you do start to see news about Cancun, and it doesn't matter what's happening. There, it's recycling the same news stories over and over. There was a situation in Cancun around that time this year, but the distance between Cancun and where this has happened, Julie, was the same distance between LA and Chicago in the United States. And so people were saying, "Don't go to Cancun or Riviera Maya for your spring break because this happened in Mexico." Well, yes, but it happened hundreds of miles away.

Julie 11:38

Right.

Ryan 11:39

would you feel the same way if you had to travel to Los Angeles from Chicago for work? No, you wouldn't. And so it's, you know, educating yourself about where you are, knowing what your resort or your cruise ship or your destination is doing, to help you. And really, to be honest, no matter where you are in the world, if you are looking for, the wrong things at the wrong place and doing stupid stuff with vacation brain, guess what? You're gonna find trouble, whether it's in St. Louis or whether it's in Portugal. So, you know, it doesn't matter what is going on in this destination, it's knowing what you can do as a traveler.

Julie 12:21

Yeah,

Ryan 12:22

right.

Julie 12:22

point

Ryan 12:23

So before we move on with several other questions that we get asked quite often, I wanna talk about where in the world is Wonder and Beyond? And when I put the information together for today, I thought back to a mother-daughter that got back recently from Walt Disney World, and this was a really special trip to help plan, Julie, because this was a mom, and the family had been to Walt Disney World about 10 years ago, and this trip was for her daughter graduating from high school, and this was a graduation gift. And so when I put together the quote, she's like, "You know, we usually stay at this type of resort. But she's like, "I just wanna see what's out there." And I found a phenomenal rate at Animal Kingdom Lodge. And so she said, "You know, I'm gonna let the daughter decide." And the daughter, chose Animal Kingdom Lodge, and I literally got a picture from them. She said, "This is what we saw when we walked into our room." And it was a picture of a giraffe outside their window

Julie 13:25

Amazing! Oh,

Ryan 13:27

And they did not even have a s- and they did not even have a Savannah view room. And so I think it was one of those things where it was like I couldn't have planned it any better, right? The mom could not have planned it any better, just to have that. and she texted me during the trip, and she just said, "My daughter just keeps saying thank you, thank you, thank you for this trip." And I just thought, wow, what a cool way to connect. 'cause it's such a special time, you know, when you grad- I mean, you'll get there, you know, as far as kids graduating from high school and kind of thinking about those transitions. And I just, I love the fact that I was able to help them with that.

Julie 14:06

Right? That's what it's all

Ryan 14:08

S- yep, absolutely. So because of those reasons and more, we love celebrating and sharing where our clients are headed, and we can't wait to hear about their trip, during the trip, after the trip, and being able to share those fun little stories All right, Julie. Question number four: what's the best all-inclusive cruise or resort for my family? I actually love this question, but this is not a simple question

Julie 14:37

Yeah, so the way that we answer this, it's we are gonna have a conversation and we're gonna talk about your family's travel style, what you're looking for in this trip, why you're taking the trip, what you're envisioning on your day-to-day. And I can guarantee you that while we're having that conversation, a cruise ship or a resort is in our mind ready to go to talk to you about. And we, you know, we're not gonna mention it right away maybe 'cause we need to go check and make sure it's available for you. but we've got those resources. So it's, it's an it depends type of answer. We're gonna have this conversation, talk through things. But, you know, I can guarantee you if you really wanted a water park in your all-inclusive resort and you Googled best resorts with a water park, you are going to get such a plethora

Ryan 15:26

Yeah

Julie 15:28

And the amount of times that a resort is going to say a luxury all-inclusive resort, and it's really like a three-star resort

Ryan 15:36

Yes.

Julie 15:37

beach, da, da, da, da, da, all those kind of things, that happens all the time.

Ryan 15:42

if you are working with somebody like us, we're gonna take the time to understand what it is you want and best match you to that. if you're booking on your own, I would suggest you take that same time and you really think about what are the things that are most important to you. And, yeah, because what's best for your neighbor down the street and the amazing vacation they had with their kids is not the same vacation that you necessarily wanna have in the same place. So take that time, d- do that. You know, don't just look at those top resorts because the first couple are gonna be sponsored and, and, or the information's from four years ago. take that time to figure out what you want or work with somebody like us to really match it for you. Our last question, Julie: how far in advance should I start planning that big trip? I'm thinking a honeymoon trip, a milestone trip, a multi-generational trip. How far ahead should I plan those big things?

Julie 16:46

if you have this trip on your mind, you reach out to me once you know that you would like to take this trip and you're interested in it. I don't care if it's two years out, two and a half years out, a year out, I want you to reach out to me

Ryan 16:59

Yeah

Julie 16:59

and then I can tell you, "Okay, this is when we'll start planning it." I have the perfect example. Right now I have a client that we work together basically year-round, but we're planning a very big Italy trip for her son's graduation for next year, and I've known that Italy is the destination for probably a good year. But it wasn't available to book. So now that we are getting into the timeframe that we can book it, we've already been talking about what's important, what do we wanna do, and now we are just in the phases of starting to make the itineraries. But because I knew about it, I already knew to start checking and looking for availability to

Ryan 17:36

Yes

Julie 17:37

once it is, we are ready to go. at least, like, nine months for a big trip, at least.

Ryan 17:44

and when we say big trip, we mean one that has a lot of logistics. Multiple flights, transfers, different places you wanna be at, different things you wanna see. Those all take time to iron out and map out and find the right fit. So, yeah, the sooner we can do that, the better

Julie 18:04

or if you have something specific, like we know that we wanna go to Turks and Caicos. I've had that request so many times this summer for upcoming travel, and it's not available because it's a popular destination. Same with certain Disney resorts around Christmastime, you know, things like that, they sell out. So if it's a popular destination or a popular travel time, definitely, further in advance is best

Ryan 18:29

Now, that being said, we've also talked about on this show that you can put a trip together rather quickly. I remember a father and son going to Universal the next week, and those trips are very unique and uncommon, but they can be done. but I would say definitely for a, quote-unquote, normal trip, you know, if you're looking at four months out, six months out, you're still gonna be able for the most part find what you want and find options that fit you. All right, Julie, as we wrap up, what's a question that you often get that we didn't have on this list today?

Julie 19:09

So I'm gonna go for a specific destination here. shocking, I'm gonna go to Disney World. And I would say almost every time I am on the initial consultation call with a client, they ask me about dining reservations and Lightning Lanes for their Disney trip, and I'm like,

Ryan 19:28

Yep

Julie 19:29

pause. We have, like, six or nine months to go. We will talk about it when it's time to talk about that. So just kind of that idea of, like, getting ahead of yourself. Like, let's get the room booked first, and then I'll guide you through the timeline of what comes next, and you don't have to think about all those kind of things until it's time to think about those kind of things

Ryan 19:49

Yes, I like that one. That's a really good one and it also shows why working with somebody who has planned these trips before, understanding kind of the timeline really makes sense

Julie 20:01

Mm-hmm

Ryan 20:02

The world is full of wonder, and your next great adventure is waiting. At Wonder and Beyond Travel, we work with you to create a one-of-a-kind journey, taking the stress off your plate so you can focus on the joy of exploring and the memories that will stay with you forever. If you're ready to start planning or you just wanna dream a little bigger, head on over to wonderandbeyondtravel.com. We'd love to help you get started. We look forward to talking to you next week on all things travel When we talk about the Las Vegas and Mighty Five National Park portion of my Canyon Spirit trip