The MapleMoney Show » How to Spend Money Wisely » Travel

How To Travel With a Large Family and Not Go Broke, with Kevin Payne

Presented by Willful

Welcome to The MapleMoney Show, the podcast that helps Canadians improve their finances to create lasting financial freedom. I’m your host, Tom Drake, the founder of MapleMoney, where I’ve been writing about all things related to personal finance since 2009.

If you’re anything like me, you’ve already begun to plan your first post-pandemic vacation. And if there’s one thing that COVID won’t change, it’s that travel will still be expensive, especially if you have a large family.

Kevin Payne is a freelance personal finance writer and the budget and family travel expert behind He lives in Cleveland, Ohio, with his wife and four kids. He joins me this week to share tips on traveling with a large family and to explain how he uses travel rewards to save money.

Many people don’t realize that traveling becomes a lot more complicated and expensive as soon as you have more than two kids. There are fewer options when renting a car or booking a hotel. And when you’re flying, not only do you have more luggage to contend with, but seating arrangements get tricky.

One thing Kevin recommends is to book an Airbnb instead of a hotel room. Not only will you save money, but the living arrangements are often far more comfortable. Renting a house with a large kitchen makes it much easier to prepare meals, and you can avoid going to restaurants as often.

Kevin shares his philosophy on travel rewards. He takes a more balanced approach than most extreme travel hackers and says that his priority is to create a wonderful experience for his family, even if it costs a bit more in the long run.

This episode of The MapleMoney Show is brought to you by Willful: Online Wills Made Easy. Willful’s intuitive online platform means you can create your legal will and Power of Attorney documents from the comfort of home in less than 20 minutes and for a fraction of the price of visiting a lawyer.

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Episode Summary

  • Traveling with a family of six
  • Why Disney is a great place to use travel rewards
  • Staying at an Airbnb vs. a hotel
  • The rates on some accommodations are negotiable.
  • How Kevin allocates his family’s travel rewards
  • The travel rewards mistake that many people make
Read transcript

If you’re anything like me, you’ve already begun to plan your first post-pandemic vacation. And, if there’s one thing that COVID won’t change is that travel will still be expensive, especially if you have a large family. Kevin Payne is a freelance personal finance writer and the budget and family travel expert behind He lives in Cleveland, Ohio, with his wife and four kids. He joins me this week to share tips on traveling with a large family and explain how he used his travel rewards to save money.

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. Do you know 57 percent of Canadian adults don’t have a will? Willful has made it more affordable, convenient, and easy for Canadians to create a legal will and power of attorney documents online from the comfort of home. In less than 20 minutes and for a fraction of the price of visiting a lawyer, you can gain peace of mind knowing you have a plan in place to protect your children, pets, and loved ones in the event of an emergency. Get started for free at and use the promo code, Maple Money, to save 15 percent. Now, let’s chat with Kevin…

Tom: Hi, Kevin, welcome to the Maple Money Show.

Kevin: Hey, how are you doing, Tom?

Tom: Good, and I’m glad to have you on. I know you have a large family so I kind of wanted to go through how you managed to travel with that. I know a lot of listeners are wondering why we’re talking about travel. But even though we’re in COVID right now, people are starting to look at what 2021 will look like. I want to run through some tips with you, especially for families and in your case, a larger family. I’ve always found things like vacations really cater towards a family of four. It’s easier to get vehicles, hotels that have two double beds. What does that look like for you traveling with six people? That must be much more difficult.

Kevin: Oh, yes, absolutely. We adopted our two daughters about 10 years ago and that was one of the first things we noticed. We had them for a year before the adoption was finalized and a week before taking a large family vacation. It wasn’t just “all of a sudden” that we looked back in the van and there were four kids instead of two. But yeah, it’s a huge thing if you stay at hotels and things like that. They’re catered to families of four or less where you only get two double beds. You can find places that hold more, but it obviously costs more. And if you use travel rewards, it costs more points or miles to do that. And sometimes those rooms aren’t available using rewards so it is a little tricky to do that. One thing we’ve done with a lot of our trips is opt doing a rental like an Airbnb or Verbo. We find that’s a lot more beneficial. A lot of times it’s a lot more cost effective for us as a family of six unless we’re trying to use up rewards we’ve saved up. That’s kind of the way we go, especially down here. We like to do a lot of beach trips or Disney and things like that. You can find rentals pretty inexpensive in places like that where they’re real close to the beach or right on the beach. For Disney, despite it being such an expensive place, is actually one of the easiest places to use rewards because there’s so many flights that go there and so many places to stay. You have a lot of options. But it is a little more difficult.

Tom: I have a couple of thoughts from what you just said. First of all, Airbnb and Verbo, the more I look at it, I’m starting to think it’s a good choice for any families, even smaller families. Quite often the price seems better than a hotel. Part of me still wants to feel pampered at a hotel but when you start looking at grocery costs of this, I assume that’s where the additional savings are—you can actually eat at the house.

Kevin: Yes. For example, I mentioned, Disney. If I stayed at a Disney resort, their hotel rooms are small. You get a little kitchenette that is two or three feet long with a microwave. We’re trying to make sandwiches and pack them for the park and it’s nearly impossible. But if we had a bigger rental or even a hotel that had a full kitchen, we’d save so much money. We could order groceries online, pick them up or have them delivered and we don’t have to go anywhere and deal with all that. And we also don’t have to pay the park prices for all their food. It’s the same thing with the hotel. The only option is if stay somewhere with the free breakfast or they have a restaurant and that’s your only choice. We’ve got four kids. They eat a lot, drink a lot and snack a lot. Having access to that kind of stuff is super helpful and saves us a bunch of money.

Tom: You mentioned Disney. You mean Disneyland or Disney World?

Kevin: Disney World.

Tom: Yeah, I just wanted to clarify that because I find with Disney World there is a lot of rental houses in the area. With Disneyland I don’t think there is as much. But Disney World, you’re right, there are all sorts of options.

Kevin: We were planning a Disneyland trip for the spring but who knows if that’ll happen or not. I have a feeling it’s not, but we’ll see.

Tom: Yeah, spring gets a little dicey next year, but we’ll see what happens. And I do like your tip that if you’re in a hotel, those ones with the free breakfast (especially going down this Disney path) it’s just a lot more efficient to quickly grab one of those quick, free breakfasts and get out the door.

Kevin: One more note on rental places like Airbnb and Verbo. You can actually message the owners of those places. If you’re going to stay somewhere for an extended period of maybe a couple of weeks or whatever, you can message them and ask if they’re willing to negotiate on that price and stuff. Just because you see it on the screen on the quote, they might be able to cut you a deal. For example, last year we went down to Cocoa Beach in Florida and rented a place real close to the beach. I contacted them—and I think was through Airbnb. The guy said he really couldn’t cut it down at all but said if I booked it outside of Airbnb through their actual rental management company, it’ll drop the $150 cleaning fee off of it. So, we saved quite a bit of money that way even if they weren’t willing to budge. If you’re traveling somewhere that’s off season, they’re probably looking to try to fill that place because they’re having a hard time finding people. That’s a great way to save some money. The one thing you do have to watch out with those is the extra fees on things like the cleaning, especially now. Also, the cancelation policies. Make sure you check that before you hit that button to reserve the place, especially now, not knowing the future of travel with how things are going. You want to have a very lenient cancelation policy. I think a lot of those places have adjusted that. A lot of people who rent out homes realize what’s going on and have adjusted their policies based on that.

Tom: Have you ever had any problems renting these houses? I hear the occasional horror story of how some people have got canceled while they were already on their way. Or the condition of the place wasn’t what they expected.

Kevin: We have not really had too many issues. We took a family trip a few years ago to Washington, D.C. and stayed somewhere. There were lots of pictures on the profile of the inside of the place but not the outside and we were definitely in a neighborhood we normally wouldn’t stay in. When we got there, the cleaning crew was still there even though it was after our check in time. She asked us to come back in an hour and when we did she still wasn’t gone so we couldn’t get in for a while. Now, I have seen it where people get canceled by the owner. They just get an email notice that it was canceled with no explanation or anything like that. I think you can see that sometimes if you look in the reviews, especially on Airbnb. It’ll automatically make a review if the owner cancels like that.

Tom: Oh, okay. That’s a good point to bring up, too, the reviews. Just like with so many other things like Uber and eBay, you can get a sense of the person you’re dealing with in advance. You also mentioned how sometimes if you’re trying to use rewards, you’ll stay in a hotel but let’s dive into the rewards a bit. How does that look for you? Are you normally using them on airlines, hotels, other options?

Kevin: For us as a family of six, when we start planning a trip, I try to figure out how many feasible ways we can get something paid for. A lot of it depends on the location. We want to try to get flights paid for with miles. And we try to get the rental car for sure. If we are opting to stay at a hotel, that’s one thing we want to do. We’ve done Universal Studios in Orlando and Disney World and have been able to get basically the whole trip paid for using points and miles, except for the theme park tickets. I probably could have figured out ways to do that but I don’t want to get nine different cards, you know. We keep a pretty sizable travel fund instead of just rewards so it’s not an issue. But we definitely always try always get flights for sure. That’s a big part of a trip for us. I grew up going on lots of family vacations driving everywhere. And I’m just sick of that so I try to avoid driving whenever possible.

Tom: I also don’t enjoy the drive. I’d rather just get to the destination as soon as I can. Speaking of getting there as soon as you can, it seems like there’s a bit of a game sometimes where you’ve got to find just the right combination of a flight to get the best value for your points. Do you ever go that deep? Or do you just go with what’s most convenient?

Kevin: I kind of lean towards the convenient side. There are people who deep dive into credit card rewards and know way more than I do and probably would tell me that I’m not getting the best value out of it. For me, as a dad and husband, the value I get out of it is just that we have a good trip. If I choose a place or airline where my stuff’s worth two cents versus three cents, it doesn’t matter to me honestly. It’s hard enough to try to find flights for six of us at a reasonable amount and having seats together in general so I don’t concern myself with that much and I don’t think other people should either. I just think the value is in planning a good trip. If we go somewhere and my wife and kids enjoy where we’re staying—where it’s peaceful and relaxing and we don’t have any issues with our flights or anything, then it’s a good trip.

Tom: I think for most people that actually enjoy travel hacking, it becomes a bit of a game. They want to get that high score, get all these credit cards and book the perfect flight that maximizes the value.

Kevin: I think if it was just me and my wife traveling it’s different. A lot of travel hackers you see online are couples or single people flying to all these other countries. And that’s totally possible to do. It’s not quite as easy to do for a family of six or a large family in general using just points and miles. There has to be some combination there unless you are just really into it and earning tons of points.

Tom: Yes, I’ve heard single people say, “Oh, we’re going to go on a cruise in Florida. Why don’t you come?” They see it as cheap. They’re buying their one plane ticket. The cruise has a great deal. But to go from Alberta to Florida is quite the flight. Even though their flight looks pretty good, multiply that by four. And in your case, multiply it by six and everything becomes a multiplier, right? The food, potentially the hotel if you need a bigger one. And everything has this extra tax on it.

Kevin: There’s no real trick for larger families. There really isn’t. It’s just a matter of having more points or more miles. There’s no secret trick to hack that.

Tom: Another thing I see, not so much with big travel hackers that might be into all sorts of programs and getting all sorts of points, but just the regular person. One mistake I think they’re making is dipping their toe into different programs. Here in Canada we’ve got our Air Miles and Aeroplan which are two loyalty programs. And then there are credit card points that are another option. It seems as if you’re doing a little bit into all of them, what you end up with is people saying, “I never have enough for a flight. How do these people even get free flights from these points?” You mentioned you don’t get into a whole lot of cards so do you find that narrowing down helps that?

Kevin: I do have quite a few cards. You can find different posts online about how to get your family of nine to Hawaii but it’s just this huge, complicated, thing of seven different cards between you and your wife—that’s what I meant about that. I do have quite a few cards but not that many I use on a regular basis. A lot of them are where I’ve got them and hit the spend limit in order to get the bonus at the beginning. Then I set them aside and just let them sit there as long as they don’t have an annual fee or anything to worry about. So yeah, you can spread yourself too thin. I think one thing that families can do is if you have a place in mind you really want to go to and want to be able to use points and miles for, stick with that one trip and start from there. Start Googling ways to get there for free or ways to use rewards for free. Most of them will have a couple of specific cards you need to get so start with those ones. You don’t have to get every single one and stockpile them. A lot of times that actually hurts you because with a lot of the rewards aren’t as flexible as other ones. Some of them are more versatile where you can use them for travel, credits, buy stuff online or get purchases erased. The value isn’t always the same for all the redemption options but at least you have. Right now, some of the popular ones here have added in being able to use them for groceries and things like that which maybe isn’t the best value in normal circumstances. But right now, when everybody’s kind of strapped for money, if you have them (points) use them for that. One thing you can do that may be useful… And this is not necessarily related to travel rewards, but say you’re staying at a hotel chain and you’re not part of their rewards program yet, sign up for it before you check in. It doesn’t cost anything. You’re not getting a credit card or anything like that. You’re just joining their rewards program. You’ll get points for every stay you have there. My son plays soccer and was at a tournament and when I looked I realized I wasn’t a member of their rewards program yet. But while we were in the parking lot I actually filled the form out on my phone, walked in and there was five or six other families from his team that were sitting in the lobby waiting for their rooms. And because I was a reward’s member for all of five minutes, they actually upgraded me to a suite and gave me the room right away. So I told everyone they could put their stuff in my room while they waited for their tiny little rooms. That ended up being one of the best trips as far as our soccer tournaments go for my son because he had his own whole huge bed in the room. There was an extra office area and a couch and stuff. He was living it up big time there. And I didn’t do anything other than sign up for their rewards program ahead of time.

Tom: One of the things that took me awhile to learn was actually on this podcast. Lee Huffman told me. I used to book every hotel and flight through Expedia. Sometimes you’d get great deals. I’m not complaining about them. But I found out you don’t get the points, though. Even if you enter your best Western loyalty number into Expedia, they track it. You might get the perks in the hotel being a member, but you don’t get the points. It’s something to keep in mind for people that aren’t paying attention like I wasn’t. You think you’re collecting this extra level of hotel points and you likely aren’t.

Kevin: And a lot of times the best deal is actually the direct deal through the place. Lee is the master. I was actually just hanging out with him online just a little bit ago. That’s something to definitely consider. If you can find a deal, great. But you’ve also got to think about if something happens with that trip where you have to cancel, that’s an extra step in there. There is a middleman in the in place that’s communicating between you and the hotel so it’s something to think about.

Tom: Yeah, I had to deal with that with the beginning of COVID. We did have a hotel booked through Expedia and for a brief moment it was kind of a run around with the hotel. I talked to Expedia and they say they don’t have a return policy unless the hotel okays it. I don’t know if it was by hotel brand or across the board, but thankfully, Expedia then did release a bunch of automatic refunds without hassle. And without you even asking for it. They just they suddenly refunded everybody.

Kevin: All the travel companies were definitely trying to scramble and figure out what to do. They still are.

Tom: Yes. One question I wanted to ask you that isn’t financially related but I’ve felt this pain before. In Canada, flying with a family of four, it seems automatic that they’ll put you together. I’m not talking about choosing your seats but just as a default you might get two and two where they try to keep people together. I don’t know if that’s part of their process or not specifically. But it seems like as soon as we get on a US flight, they almost go out of their way to break us apart. With you flying in the US, how terrible is that for a family of six?

Kevin: It’s not as bad now that they’re older. Our kids are 14 years or so and if they all had to sit together… Actually, they’d probably prefer to sit by themselves or with a stranger than with us anyways. But, when they were younger, one of the first thoughts when booking flights was finding a way to get us all together. A lot of the airlines do that because it’s an upcharge to have the ability to pick your seats, basically. They’ll have several different levels—a business one or maybe you want another half foot of leg room. With things like that there is always an upcharge. We prefer Southwest Airlines. The funniest thing with that is, they don’t allow you to choose your seats at all. It’s kind of a free-for-all but we have never had issues getting everybody together. The thing with them is that they open up 24 hours beforehand to check in. And when you check in, you get your boarding group so it’s based on where you’re boarding group is and whether you’re going to get a good seat or not. I think they have like a EarlyBird check in where you can just pay an extra fee, per flight, and they automatically check you in at the earliest possible time so you’ll get the best possible boarding group unless you’ve purchased a business ticket or something like that. That is one thing I’m willing to pay for. It hasn’t been that big of a deal but it’s something families have to deal with, for sure.

Tom: They really did seem to go out of their way to split us up. One of our kids was less than two years old at the time and we were all split up so we knew that wasn’t going to work.

Kevin: Yeah, that’s not cool.

Tom: I’ve never been on Southwest because I don’t think they do international flights into Canada. I’ve heard great things and I do want to try them. Canadians can certainly use them but it would be within the U.S. I definitely do plan on trying them out at some point because I’ve heard great things.

Kevin: I didn’t think about that. I’ve actually never flown into Canada before. Any time I’ve ever visited has been driving because we’re relatively close to the border.

Tom: The other thing around the flight I find interesting is luggage. As a family of six, does everybody have their own bag? Do you try to reduce that bag count?

Kevin: Actually we’ve never had an issue with this at all and it probably relates to fly mostly Southwest. They don’t charge fees for the first two bags per person and a carry on so we’re pretty good there. For the most part, everybody has a suitcase and a carry on bag like a backpack and a personal item like a jacket. And that’s about it anywhere that we go. When they were younger, the boys would be in one suitcase and the girls in the other just to make it easier to carry them. But now that they’re old enough to carry them themselves (whether they do or not is another story) it’s not really an issue for us. I know with other airlines there’s baggage fees and stuff. But I think on my end, I’d just pay the fee to have the bag instead of trying to cut stuff out that we might need while we’re on vacation. We do try to pack relatively light. There are certain trips that just you have to have certain stuff. Going down to Florida you’ve got to have a bunch of sunscreen. If you buy it down there it’s something like $20 a bottle so you want to take that with you. But it’s not a huge issue.

Tom: Here in Canada, both of our major airlines charge for bags. One of the easy tips is there are certain credit cards connected to these airlines. Some have no annual fee that’ll give you that free bag or maybe even multiples. And especially when there’s no annual fee, if you use that one just for booking your flights, it’s not such a bad deal. Some of them will include a companion flight once a year or something like that with no annual fee. I’m fine with annual fees but then you got to do the math. You’ve got to make sure you’re definitely going to use the companion flight and those kind of things. You’ve got to make sure you’re getting your value out of it.

Kevin: And there are a lot of cards that will waive it the first year but then you’ll have to think about it the second year and beyond. Then you have to decide whether you want to keep that card. Is it worth the $90 or $95 annual fee you’re paying? So you’ve definitely got to do some math there for sure. I think we have a couple of cards that do allow us the bags. We just don’t tend to fly those airlines as much. I guess it depends on where you’re located at and if it’s a hub or whether you get good flights or not.

Tom: The more cards you get, it does start to feel a bit like a game because one might be your flight booking card and another gets a better percentage cashback when you shop for groceries. You might need a chart to start taking care of it.

Kevin: Yeah, I keep meaning to make a little card that would fit in my wallet that tells me which one to use for each thing.

Tom: Exactly. Is there anything you think we’ve missed here that that might help large families looking to travel?

Kevin: I think we’ve covered quite a bit of stuff here for sure. I think a lot of it just comes down to figuring out where you want to go, figuring out the best way to get there and trying to provide a good experience for your family, especially right now with all that’s going on. There’s a lot of extra stress, a lot of extra anxiety around just life in general. So obviously, you want to be safe if you’re going to travel places. I don’t know about up in Canada where you’re at, but here a lot of people have been opting to do more regional trips. In Ohio, we have a few different areas that are really nature forward places that have a lot of cabins you can rent. We did that during the summer just as a way to get away as a family. It wasn’t very expensive. It’s not one of our normal, full-blown family trips, but we actually got a place that was pet friendly so we were able to take our dog with us and go do some things we normally wouldn’t do. Travel doesn’t always have to include a hotel and taking a flight somewhere. If you want to find stuff to do, there’s probably stuff within a two or three hour drive from you that’s worth checking out.

Tom: Yes, they say to go to another city. I’ll go to the museum, to an amusement park. I’ll do all those things. I haven’t gone to the museum in Edmonton forever. Or in Calgary when I didn’t live here. So there is something I’m missing out on by not checking out some of the local things. One thing we did in the summer was rent a houseboat. I’d never done that before. Especially this summer, in 2020, it seemed like the perfect social distancing thing to do. It was just two families out on a boat with nobody else around.

Kevin: Yeah, houseboats, rent an RV… Those are things that are really popular right now. Even heading into the winter, I think there are ways to escape without putting your family in harm.

Tom: Well, this has been great. Thanks for being on the show.

Kevin: Yeah, thanks.

Thank you, Kevin, for the tips on traveling with a large family and for inspiring us to start planning our next vacation. You can find the show notes for this episode at I want to take a moment to thank you for listening to the Maple Money Show. I appreciate your support in helping us continue to grow. If you have the Apple podcast app on your phone, can you pull up Maple Money and give it a quick rating? Even better, leave a review to let everyone know what you think of the show. I look forward to seeing back here next week when we’ll have Romana King on the show to discuss how we often overestimate our financial knowledge.

Disney, despite it being such an expensive place, is actually one of the easiest places as far as rewards, to use them, because there are so many flights that go there, there are so many places to have a lot of options. Click to Tweet