9 Common Family Travel Planning Mistakes (and How to Avoid Them)

Avoid these 9 common family travel mistakes! From booking too late to overpacking, learn how to plan better trips with kids and save money with points & miles along the way.

Planning family travel doesn't have to be overwhelming. In this episode of Family Travel Unpacked, Melissa shares the 9 biggest mistakes families make when planning trips with kids—and exactly how to avoid them. Drawing from nearly 15 years of family travel experience, including a two-year backpacking gap year with kids, Melissa covers everything from booking timelines to packing strategies to creative flight routing.

Whether you're new to travel with kids or a seasoned family traveler, these practical tips will help you plan smoother, more affordable trips that everyone actually enjoys.

Timestamps:

00:00 Welcome
00:44 Mistake #1: Waiting Too Long to Book
02:46 Mistake #2: Planning Without Everyone’s Needs in Mind
04:14 Mistake #3: Overpacking Your Itinerary
06:40 Mistake #4: Being Too Rigid With Flights & Routing
10:16 Mistake #5: Under-Researching Weather & Microclimates
12:04 Mistake #6: Overpacking Your Suitcase
14:56 Mistake #7: Not Preparing for Travel Day
16:37 Mistake #8: Not Using Points & Miles Strategically
18:31 Mistake #9: Thinking Short-Term
19:55 Wrap-Up

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Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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Transcript

Melissa 0:02

Hey there and welcome back to Family Travel Unpacked. I'm your host, Melissa, and in case you're new here, you can always find tons of detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com. And if you've been enjoying the show, be sure to hit follow wherever you're listening so you never miss an episode and drop a five star review- it really helps other families find the show. So today we're talking all about the things I wish I could go back and tell myself before we started traveling with kids- the biggest mistakes families make when planning travel, and more importantly, how to avoid them. And listen, I've made basically all of these mistakes myself at some point over the past 14 years of traveling with kids. So this comes from a place of hard won experience, not judgment. Mistake number one is waiting too long to book. This is probably the biggest mistake I see, and honestly, I'm dealing with it right now as we speak. It's February and I'm trying to plan our big multi-generational vacation for December, so I'm 10 months out, right? You'd think that's plenty of time. Well, this week in the span of 24 hours, I lost out on three Airbnbs. These were the only properties in the exact spot I wanted to stay that were big enough to fit our group of 14 people. I was literally messaging with the hosts, asking questions about the properties, and all of a sudden they changed to unavailable. Someone else booked them right out from under me, and that's just accommodations. If you're using points and miles for flights, award availability opens up about 10 or 12 months in advance, depending on the airline. And the best seats, a lot of times they get snagged immediately. Whether you're looking for business class to Europe, those coveted nonstop flights or seats together as a family, all of it can go fast especially if you wanna visit popular spots like Hawaii, Italy, or Japan. You could be left with options ranging from bad to worse, whether that's because the tickets cost more points than you have, or they force you into an extra stop. So what I do is I keep a where to go when spreadsheet, I talked about this back in episode three. Across the top, I have our school breaks, like winter breaks, spring break, summer plus, all those long weekends, and down the side I have years. Then at the bottom of each column, I brainstorm destination ideas that might work for that time period. Once I know our school calendar for the following year, which our district publishes pretty far in advance, I can start booking right away when award availability opens up. And here's the beautiful part about award bookings. Most of them are fully cancelable and refundable. So if your plans change, you're not stuck, maybe you decide to go somewhere else, or the dates just don't work, it's okay. But that means you can book early without fully committing. And it gives you flexibility while still securing those prime seats. The bottom line is 10 to 12 months out is not too early. In fact, for popular destinations and popular travel times or big groups, it might be barely enough time. I can't stress this enough. Don't wait. Mistake number two, not considering everyone's needs and preferences. Okay, so in my family we've got our son who's 14 and he likes the outdoors, but only in cooler temperatures. Our daughter's 11 and she loves a nice resort, good food, shows in big cities. As I've mentioned before, she has celiac disease and that definitely adds a wrinkle to our planning. My husband is open to all types of travel, but let's be honest, he's really just there for the food. And I love getting outdoors when we travel, but I'm also a sucker for beautiful architecture. And in the winters we travel with my mother-in-law, who has some mobility challenges, along with some older nieces and nephews and younger kids. If I only planned trips that I wanted to take, we'd be on snorkel boats every single vacation. I love it, but unfortunately that wouldn't be everyone else's

3:30

favorite, so I've gotta compromise.

Melissa 3:32

What I've learned is to alternate and blend. We'll do an adventure trip like Costa Rica, where we spent half the time doing things like zip lining and wildlife tours, and then the other half at a nice resort where we could decompress by the pool. And then maybe the next trip is more city based. Like when we spent time in Italy visiting different towns, eating amazing food and seeing all the history. The key is making sure that everyone gets something they're excited about, even if it's not on every single trip. Over the next few months, we'll see beautiful cities in Portugal, take in shows in London, hike in the Azores, and lounge by the pool in Arizona. There's something for everyone in our plans and honestly, having different preferences in the family has made us better travelers. We see and do things that I wouldn't have thought of on my own, and everyone brings their own excitement to different parts of the trip. Mistake number three. Overpacking your itinerary. Man, I am so guilty of this almost all the time. I get excited about a destination and I wanna see and do absolutely everything. So I try to pack our days from morning to night, and then the reality hits. The kids are tired. Someone needs a bathroom break at the worst possible moment. The museum that I thought would take two hours takes three, and I haven't been really honest with myself about travel time between locations or the trains just running three hours late. Suddenly people are melting down. Someone's getting frustrated because we've been go, go, go for six hours straight. I learned that lesson the hard way on our first evening in Tokyo. I talked about this on our Japan episode. We'd had a really long travel day, one stop in San Francisco, and then the long flight to Tokyo. The kids were fine on the plane, and for most of the day as we were walking around. But that first evening, I'd booked us on a food tour, and my son completely melted down. He was exhausted, overwhelmed, and we pushed him too hard, too fast. I really understand. I don't blame him at all. If your kids are on the younger side, really try hard to build in some downtime. Like if you've got a morning activity, maybe the afternoon is gonna be lowkey pool time, or just wandering around a neighborhood at your own pace and stopping for ice cream until you find a great playground. Even now, if we've got a big day planned, I build our itinerary so that the next day is intentionally lighter. And I really try to factor in that first day or two for adjustment, especially if we've got a lot of jet lag to contend with. Like on our upcoming trip to Portugal, we'll land early in the morning and the only firm plan I have for that day is a 4:00 PM tuk tuk tour around the city. I think the kids will really love it and it doesn't require a ton of energy on their part. Now with older kids, sometimes I'll give them the option to hang back if Ronnie and I wanna do something different. On our last day in Italy, I could tell the kids were wiped out. Jacob and I had already been there for two weeks, and Ronnie and Shoshana were just there for a little bit less. We'd taken them all over and experienced so many different things. Since we were staying at a nice, well-staffed hotel and they had wifi to get in touch with us if they needed to, we let them stay behind at the hotel and relax while we took the ferry over to ano. I think the kids would've liked it, but honestly, they were so grateful for a few hours to hang out, and I think it really meant a lot to them that we were paying attention and could see what they needed, even though they would never have asked. Plus, Ronnie and I got a little mini date out of it, which was nice. After being with the kids 24 7 for so long. Your kids don't need to see every single site in a city to have an amazing trip and get a taste of what's out there. Mistake number four is being rigid with your travel arrangements. This can be tough. Back when we lived in LA we'd decide that we wanted to go to Europe and just book whatever nonstop flight looked good and needed the fewest points. Now that we live in Columbus, Ohio, we have basically no international direct flights. I'll be honest, it is so much harder, especially since we wanna avoid my husband and kids taking off extra time just to accommodate a really long flight itinerary. It would be easy to just accept the situation and either pay premium prices or deal with complicated connections. But getting creative with your travel arrangements can open up some amazing opportunities and sometimes make your trip better. Here's a perfect example from our upcoming Portugal trip. Both cash and award flights from Columbus to Portugal were super expensive, and repositioning flights to the major East coast international airports we re outrageous. Several hundred dollars per person for an hour long flight on a cramped shuttle service, unless we wanted to sit around in a connecting airport for 12 hours. That would've required my husband and kids to take off an extra day, and it just wasn't in the cards. So I initially booked US reasonable tickets out of Cleveland. It's around a two hour drive, and we'd still have to stop in Newark. My plan was to pick up a rental car here in the morning and then drop it off at the Cleveland airport since our much more reasonable return flight brought us back home. The overall itinerary was basically fine, but I promised the family that I'd keep looking. No one was excited about a two hour drive, two hours of sitting in the airport, and then two flights. And that's to get to the closest country in Europe, right? So we started looking around and found reasonable award tickets from Dulles Airport outside of Washington, DC. But the flights from Columbus to Dulles were way too expensive. I'm talking about almost 30,000 points per person. Just crazy stuff. Now, one thing I haven't mentioned on this show before is that I'm originally from the DC area, and my side of the family still lives there. So here's what we're doing instead: we're flying into National Airport earlier in the day to give ourselves plenty of buffer. And then we get to have dinner with my mom and my brother who live in the area before we head to Dulles for a late night flight. The tickets to National were a lot cheaper than they were to Dulles, and we're able to use our Southwest companion passes so the kids fly free anyway. We're saving time, money, and points- plus we get some much needed family time we wouldn't have had otherwise. When I told the kids about the new plan, they were so happy, and honestly, I can't believe that I hadn't thought of this idea sooner. So that's what I mean about getting creative. Don't just accept the first routing you find if it's not exactly what you're looking for. Use tools like FlightsFrom. I enter my destination as the origin point and look at the map view to see which US cities have direct flights to where I wanna go. Then I check award availability and cash prices from Columbus to those gateway cities. And then, let's be honest, I turn the whole thing over in my head a million times to see what angle makes sense. Sometimes it means driving two hours to a bigger airport is worth it to get a direct flight to Europe instead of connecting through a hub anyway. Sometimes it means flying into a nearby airport and making it part of the adventure. Sometimes it means building in a stopover somewhere interesting instead of just viewing it as an inconvenience, like maybe an overnight in New York. And here's another simple trick maybe just reversing the order of your itinerary can give you better or cheaper flights or open up more accommodation options like if you were planning to start in Barcelona and end in Madrid, but the flights to Madrid are way cheaper or have better reward availability, just flip it. Start in Madrid and end in Barcelona. The point is be flexible and creative. Think outside the box. That problem of not having direct flights from your home airport could turn into an opportunity for family time, exploring a new city or finding better reward availability than you would've had otherwise. Mistake number five is a tough one under researching the weather and climate. This seems obvious, but it's easy to forget when you're dreaming about a beautiful destination. You see that gorgeous photo and read amazing review, and you book the trip without really thinking about what the weather will actually be like when you're there, and how that factors into the activities that you wanna do. Like if you hate being out in the rain, you probably shouldn't book a place like London in January. And if you wanna hike in the Dolomites, you'll be really limited in April or May even though the rest of Italy is perfect then. And then some places aren't even safe for strenuous outdoor activities in the worst summer heat. But here's the thing, weather research goes beyond just looking up average temperatures and rainfall, especially if you're planning on any outdoor activities. You need to dig deeper, especially for destinations with microclimates. Take Hawaii for example. Let's say you wanna go in the winter. I know I do. We've done it and we're debating doing it again, but different parts of each island have completely different weather patterns. The windward sides tend to be much wetter and the leeward sides are drier. And winter swells can make certain beaches completely unswimmable and unsafe for kids. But there are protected bays on each island that are perfectly calm. So you need to look up which parts of the island will be wet versus which will be dry during your visit, which beaches are protected from winter swells, where the best conditions are for the activities you wanna do, and then try to plan your hotel to be in the right area. That's way more detailed than just"Hawaii weather in January". Before you book, actually do this deeper research, think about whether your family does well in the heat, if anyone gets grumpy when it's cold, if rain is gonna ruin your plans, or just be minor in convenience. And for places with varied geography or microclimates, figure out exactly where on that island or in that region, you should base yourself for the best weather during your specific travel dates. It makes a huge difference in how much everyone enjoys the trip. Mistake number six, overpacking, and I don't mean your itinerary. This is a big one that we learn the hard way. Overpacking can get expensive. Checking multiple bags adds up really fast. It's also physically exhausting to schlep a ton of gear and suitcases around, especially if you have young kids who can't help carry things. And you'll ultimately feel stressed out and cramped when your stuff has exploded all over the hotel room. I will never forget our first trip to Maui with our son when he was a baby for so many reasons. But talking about overpacking, we had two huge suitcases plus our carry-ons because we thought we'd need everything from home. It was a nightmare. We were constantly digging through bags, our room was a disaster, and we paid a fortune in baggage fees. I still remember when Ronnie dropped Jacob and I off at the airport with all our luggage at the end so that he could go return the rental car. I knew we'd have to run all the bags through the agricultural inspection station, but I was literally moving this huge pile of stuff about two feet at a time because I had to keep going back and forth, and I didn't wanna leave anything behind. Meanwhile, I had Jacob strapped me in a carrier and there's sweat dripping everywhere. Let's just say it wasn't pretty. But here's what I've learned since then. If you're traveling with a little one, you can rent things like pack and place bouncy seats and play mats at your destination. Just don't rent car seats. Bring those on the plane and use them. They're way too important for safety to trust a rental, plus your kiddo is safest using it on the plane anyway. For clothing, you have options. Either get a place with laundry in the unit or plan to rewear. And here's something a lot of people don't realize. It's surprisingly affordable to send out your laundry in some destinations. You don't have to sit around washing stuff yourself. It can actually feel like a luxury to have someone else do your laundry while you're on vacation, and it might only cost you$20 or less for basics like socks, underwear, your husband's disgusting gym clothes. Love you, honey. I also make sure to use packing cubes for everyone's clothing. It's a natural way to force your family to think about what they're bringing. Like you could decide that each of you gets two medium cubes, that's it. They also make it so much easier to unpack and repack, plus each person's stuff is separate. I'll link to the set that we really like down in the show notes. They open on three sides, so I unzip them all the way and fold the lid underneath to put them in the dressers when we get to our hotel. And I always try to store the empty suitcases while we're not using them to keep our room uncluttered, whether that's in a closet under the bed, or even just in a corner of the room. Then I make my kids spend a few minutes every morning and every evening putting away their stuff. When you're all sharing the same space that little bit of effort makes such a difference. Plus, if we're staying at a hotel or we're on a cruise, I really want things to be tidy so it's easier for the hardworking staff to get in and clean. The bottom line is you don't need to bring nearly as much stuff as you think you do. And traveling lighter makes everything easier- getting through airports, moving between destinations, keeping your space organized. It's really worth thinking through what you actually need versus what you think you might possibly need. Mistake number seven, not preparing for your travel day. This is about more than just packing. It's about mentally and logistically preparing for what the actual journey is gonna be like. There's a lot of really basic stuff that's easy to overlook. A few days before any trip, I start reminding my kids to download the shows they wanna watch on the plane, charge all their devices. We stop at the grocery store to buy snacks so that I don't have to buy a$7 bag of chips at the airport. I also talk to the kids in advance if there are gonna be any screen time restrictions or expectations, like on an overnight flight to Europe, I might need them to actually sleep, not stay up all night watching movies. When the kids were little and we were flying from la, I'd tell them something like the first flight will be a screen flight and the second flight will be a sleep flight. Setting those expectations ahead of time, avoids battles on the plane. Now that they're older for overnight flights, we talk about what they might need to be comfortable. My teen likes a light blanket and a Tylenol pm like his mom, and my daughter likes a sleep mask, a stuffed animal, and dad's shoulder. But here's what I didn't prepare for on one trip: our flight to Costa Rica got diverted mid-air due to ground radar issues in Honduras. I think I told that whole story back in episode five if you wanna go have a listen. We ended up going all the way back to Florida and spending an extra night before our rescheduled flight the next morning. That's the kind of thing that can totally derail a trip if you're not prepared for the possibility of disruptions. That's why I always keep an annual travel insurance, or at least make sure I'm using a credit card like the Chase Sapphire that has great travel protections. Always. And for really long trips, I pack essential things in our backpacks, a change of clothes, medications, important toiletries, so that we don't have to rummage through fully packed suitcases to get what we need in a pinch. And that's extra important if you plan to check your luggage. Now on to mistake number eight, not using points and miles strategically. If you've been listening to this podcast for a while now, you hear me talk about this a lot, but it's so important if you wanna travel more for less money. A lot of families approach trip planning by saying, we have X dollars to spend on this vacation, and then they try to fit everything into that budget, paying cash for the whole thing. Now, I don't know about you, but I don't have the funds for that. Instead, if you use points and miles strategically to cover your biggest expenses, we're talking about flights and hotels primarily, that's where you can really stretch your travel budget further. Now, I know not everyone has the flexibility to earn tons of points or wants to get into the credit card game, and that's totally fine, but if you do have some points or miles or if you willing to explore that world a bit focusing on using them for big ticket items can make a huge difference. I put together a free ebook to help you get started. You can find that link down in the show notes, or you can go to thefamilyvoyage.com/freetravel. Instead of just looking at cash prices and picking the cheapest option, I look at where I have award availability, where I can book hotels on points and then our actual out-of-pocket costs end up being way lower. Like when we went to Hawaii with the kids for spring break a few years ago, we used Southwest Points and companion passes and paid something like$70 out of pocket for the flights for our family of four, and that included island hopping. The other advantage of that approach is that it can open up destinations you might not otherwise consider affordable. Flying a family to Europe sounds expensive, but if you're using points, suddenly it's a lot more accessible. A nice resort in Costa Rica might stretch your cash budget, but on points it's totally doable. Now, I'm not gonna lie and say that we spend zero money on trips. Of course not. We still pay for food, activities, ground transportation, all of that. And if using points of Miles isn't for you, or if you have a fixed budget you need to work with, that's completely valid. You have to do what works for your family. But if you're able to incorporate points of miles into your planning even a little bit, can really help you travel more often or upgrade your experiences without spending any more actual money. The final mistake I wanna talk about is thinking short term instead of long term. This is really about mindset. A lot of families plan trips one at a time in isolation. They decide they wanna go somewhere, they plan that trip, they go, and then months later they start thinking about the next one. But if you wanna travel more consistently as a family, it helps to build a system rather than planning each trip from scratch. That's where my where to go when spreadsheet that I talked about before comes in. I'm always thinking ahead, always brainstorming ideas, always looking at how our school calendar lines up with different destinations best seasons so when it's time to actually book something, i'm not starting from scratch. I already have ideas to work with. I'm also always keeping an eye on award availability and different hotel deals, even if I'm not actively planning a specific trip. It just helps to keep your ear to the ground and know what's out there. If I see great availability open up for somewhere on my list, I might book it even if it's a year away, just because I know it's cancelable if plans change. That approach has led us travel so much more than we would have otherwise because instead of travel being this big, overwhelming project we have to tackle from scratch each time. It's just a part of our ongoing family rhythm. Now I realize not everyone wants to be this proactive about travel planning, and that's fine. But even small steps toward thinking systematically, like keeping a running list of destination ideas or signing up for one travel credit card and learning how to use those points to the full effect that can make your future trips easier and more affordable. Okay, so those are the nine biggest family travel planning mistakes I see. And honestly, ones I've made myself over the years. The good news is that these are all totally fixable mistakes, and even if you've made them before like I have, you can adjust your approach for future trips. We're all learning as we go. Figuring out what works for our specific families. If you want more detailed guides on any of these topics, like how to use points and miles, destination specific advice, packing tips, all that, head over to thefamilyvoyage.com. I've got tons of resources there that dive deeper into pretty much every aspect of family travel. And if you found this episode helpful, I'd love it if you could share with another family who could use some help. Hit that follow button so you don't miss future episodes. And if you've got a minute, leaving a five star review really does help other families find the show. Thanks so much for listening, and I'll see you next time on Family Travel unpacked. Safe travels!