How to Choose Your Next Family Destination

Get family travel planning tips from a mom who books 10-12 months ahead! Learn how to choose destinations based on your family's schedule, using points & miles, weather, flight routes and more. Family Travel Unpacked host Melissa shares her "Where to Go When" spreadsheet system, real examples from Costa Rica and Italy, and how to balance everyone's needs with you travel with kids - from outdoor adventure to resort pools. Perfect for families juggling school schedules, dietary restrictions, and multi-generational travel.

00:00 Welcome to Family Travel Unpacked

01:11 Understanding Travel Constraints

03:23 Flight Logistics and Planning

04:39 Balancing Family Needs and Preferences

05:26 Maximizing Points and Miles

06:34 Organizing Your Travel Plans

08:46 Weather Considerations

12:24 Making the Final Decision

14:44 Recap and Next Episode Preview

Hosted by 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

0:02

Hey there and welcome back to Family Travel Unpacked. I'm Melissa, and in case you're new here, you can find tons of detailed destination info, travel guides hacks, and more on my website, thefamilyvoyage.com. If you're listening to this, I'm guessing you've got that travel itch. Maybe you know you wanna take a family trip, but you're staring at a world map feeling completely overwhelmed. Or maybe you and your partner have different ideas about where to go. One of you wants adventure, the other wants culture. Meanwhile, the kids just wanna know if there's a great pool. I get it because choosing where to go might actually be the hardest part of family travel planning. Today I am gonna walk you through exactly how we decide where to travel next. I'm talking about the framework we use to balance weather, budget, flight routes, school breaks, and what the kids actually wanna do, because let's be honest, if they're miserable, nobody's having fun. I'll share real examples from our own trips, including some destinations that were absolute wins, and a couple that taught us valuable lessons along the way. By the end of the episode, you'll have a practical system for choosing destinations that work for your whole family. So let's dive in. Okay, so here's where most people start. They see a gorgeous photo of Santorini on Instagram, or their friend just got back from an amazing trip to Japan, and they think, huh, that's where we should go. Of course, I love dreaming big and getting inspired by other people, but that's actually the wrong place to start. Here's what we do instead, since I'm a pragmatist. We start with our constraints. The first constraint: time. Our kids are in middle school now, which means they can only miss one or maybe two days of school max. So we're working with scheduled breaks: Thanksgiving, winter break, spring break, summer plus a couple of long weekends. Those are our windows, but here's a trick: our school district publishes next year's calendar about a year in advance. I'm recording this episode in October of 2025, and I already know when spring break will be in 2027. This is huge for planning because it means we can book flights and hotels 10 to 12 months out, which is exactly what we need to get the best availability for points and miles. Of course, our kids have lives beyond school and these days they're more committed than ever to their activities. I applaud their dedication, but it also really limits our flexibility-between soccer tournaments, school musicals, and sleepaway camp. It's a lot to navigate. Some families travel during off peak times and pull their kids out of school. That hasn't been our choice since the kids were in elementary school, but it might work for your family. If your kids are younger, especially preschool age, you'll have a lot more flexibility from the school side, and they aren't going to be as focused on their other activities. Back when our kids were in daycare and preschool, we always got away during random weeks of spring and fall. Those trips were amazing because the weather was perfect, the crowds were thin, and the prices were much less than we would have to pay now during those major school breaks. Like most families, we also have to keep work constraints in mind. While I work exclusively for myself. My husband has a nine to five job That also includes plenty of weekend responsibilities and even some weeks of summer when he really needs to be in town. There are also some religious holidays when we absolutely won't travel, and other periods when we have extended family commitments. The point is, know your timing constraints first before you decide where you're going. Second constraint: flight logistics. We live in Columbus, Ohio, and we basically have no direct international flights. So for international trips, sometimes we're driving to Detroit, Pittsburgh, Cleveland, or Cincinnati to catch a direct flight, or we have to connect somewhere within the United States. This matters because it affects where we can reasonably go. A trip that requires two connections and 20 hours of travel is gonna be a much harder sell for our family than a trip with one connection and 10 or 15 hours of total travel time. There's an amazing tool called FlightsFrom.com. You'll enter your destination as the origin. Look at the map, and it shows you which US cities have direct flights there. This helps us figure out which airports within driving distance make the most sense, or if we'll definitely have to fly somewhere for a connection. Another reason it's really important to figure out your timing first, is that flight schedules don't stay the same year round. When we were initially planning our upcoming spring break trip to Portugal we planned to start or end our trip in the Algarve region in the south, which would mean using the airport in Farrow. But then I realized that there are no nonstop flights back to the US at that time of year. We would've had to leave at 5:00 AM to take a three hour train ride and then spend 15 hours traveling home. Our third constraint are our kids' needs and preferences. Remember what I said about my son referring cool weather in that last episode. That's a real constraint. We could force him on a trip somewhere brutally hot in August, but why would we, he'd be miserable, which means we'd all be miserable. Our daughter's celiac disease is also a constraint. Some destinations are really difficult, like Japan, while others are amazing like Costa Rica. And then there's my mother-in-law who travels with us for winter breaks. She moves kind of slow these days and she has some trouble with stairs. So we have to think about accessibility, walking distances and transportation options if she's coming with us. These aren't problems to solve, but they're realities that our family has to consider. And I'm sure your family has its own needs. The fourth constraint for us is points and miles availability. This is really huge for us. We prioritize destinations where we can use points and miles to minimize our hard costs like flights and accommodations. That means we're often looking at places with good award availability, hotels that participate in programs we use and flight routes where we know we can find award seats at reasonable rates. Notice I didn't say budget as a constraint. That's intentional. For our family, we don't set a firm dollar amount for the budget upfront. Instead, we focus on maximizing points and miles, which naturally keeps our out-of-pocket costs low. Obviously that's gonna be different for every family. If you aren't big foodies, you can always focus on destinations where the cash rates are low enough for accommodations that you could book a vacation rental through the Capital One portal to apply the$300 credit from the Venture X, for example. That's a great option if you're on a tight budget, especially since you can erase any remaining cost if you want. You'd still wanna make sure that flights are available on points so that you aren't working hard to save in one area and busting the budget in another. Okay, so once you know your constraints, how do you actually organize all this information? I use the spreadsheet. It's not fancy, but it works. Here's how I set it up. School breaks, go across the top: labor Day, weekend, fall break, Thanksgiving, winter break, president's Day, weekend, spring break, summer. Years go down the rows, 2025, 26, 27, and so on. At the bottom of each column, I have a running list. Of destination ideas that might work for that particular break. So on spring break I might have Costa Rica, Peru, Portugal, Morocco. Under summer it could be Norway, Iceland, Alaska, the Canadian Rockies, places where summer is actually the best time to visit. I'm also keeping in mind how much time we'll be able to take for each of those trips. Usually we can manage 10 days or so for longer breaks, and three or four days for shorter trips. But it doesn't make sense for us to try to cram a huge overseas trip into a long weekend. And to me, it would feel like a wasted opportunity to use one of our longer blocks for a place I think we really only need a few days. The beauty of this system is that it's organic. I don't use some complicated decision matrix or scoring system. We don't feel forced into any decisions. I just look at the options, think about what makes sense for that particular break and start researching. And sometimes the destination moves around. Maybe I was thinking Portugal for spring break, but then I find amazing award availability for summer instead. No problem. I can move it to the summer column if it still makes sense in terms of weather and how long the trip would be. With one kid on the verge of high school, we also know that there are some other time constraints on the horizon, things like band trips and black belt testing. Even if they're a few years off, I can put them in the spreadsheet to help me see the big picture and make the Most of the time our family still has to travel together. The other thing the spreadsheet helps me do is balance trip styles. I know that everyone in the family has different likes and dislikes, and since we're fortunate to travel a lot, it's easy to make sure we're covering all our base. In a given year, I'll try to plan an outdoor adventure trip, something that's more focused on cultural experiences and some chill time when we can just recharge on the beach or in the pool. Okay, let's talk about weather, because this is where some people make their biggest mistakes. Here's the thing, every destination has an ideal time to visit, but that ideal time might not line up with your school breaks. We went to Northern Italy in July, and a huge part of the draw was hiking in the Dolomites, which you can only do for a limited time every year. But the other parts of Italy we visited were hot, really hot. We knew that going in, so we planned around it by building in breaks to sit back and enjoy some gelato. I also packed a misting water bottle that we could spray ourselves with sly, but it made a huge difference. Compare that to Costa Rica in March, which is the dry season. I'll be honest, that it was a lot hotter than our son would've liked. But we wanted to avoid the heavy rains that can cancel some experiences we were excited about and sometimes cause bad road conditions. We navigated the heat by doing early morning activities and spending afternoons at pools or in air conditioning. Now here's an interesting counterpoint. Our friends went to Costa Rica in June, which is technically the rainy season, but they said it rained for maybe an hour each day, and it was a lot cooler than our March trip. Plus everything was much less crowded and cheaper. So sometimes the off season is actually better depending on what you value. The key is this: research, typical weather for your destination during your specific travel dates. Don't just Google best time to visit. Look at the actual temperature ranges, rainfall patterns, and think about your family's tolerance levels. And be realistic. If somebody in your family hates the heat, don't book a desert trip in August thinking you'll just deal with it. You won't enjoy it, and that resentment can color the whole trip. Let's get practical and talk about getting there because this is where a lot of families get tripped up, whether it's because of the cost of flights or the intensity of travel days. When we were planning our Japan trip, we knew it was gonna be a really long travel day. We flew cross country for a stop in San Francisco and then onto Tokyo. It was a full day of travel. But here's the thing: for us, one stop is manageable. In theory, the kids could get off the plane in San Francisco, stretch their legs, get some food, reset a little bit. Side note, our flight from Columbus was almost four hours late, so none of that happened. If we had to make two connections that day would've been even more brutal, and there's a really good chance that we could have missed the flight to Tokyo. Now, I used three main tools to start searching for award availability. Points. Yeah, award tool, and point me. None of these is totally comprehensive. You'll always need to verify with the actual airline, but together they give you a good starting point for knowing what's possible if you wanna book your flights on points. By the way, I currently use the free version of all of these tools. You don't have to spend a ton to make your points work. though was probably worth paying for one of them at some point. And here's a pro tip. Award availability often gets released 11 or 12 months out. So if you're flexible on dates within your school break, you can really ramp up your chances of finding good award seats. For us, booking early isn't just about getting the flights we want. It's usually about getting everyone on the same flight. Finding four award seats together is much harder than finding two, especially if you're trying to book premium economy for an overnight flight. So we usually book as soon as that availability opens up, though I try to stick with flexible options in case something comes up and we have to shift by a day or two. The other thing to consider is connection cities. Some of them are much easier than others, especially with kids. We love connecting through Denver, for example. It's a big airport with plenty of food options, and we have access to several lounges there, but it's not so overwhelming that we can't navigate it easily. Okay, so you've got your constraints mapped out, you've checked the weather, you've looked at flights. Now is time for the negotiation phase. How do you balance what everyone wants? Ronnie and I like different things. He enjoys good restaurants. Not necessarily fancy places, but hole in the wall, local joints with great food. He also likes culture and history. I like culture too, but I also really enjoy snorkeling, kayaking, and hiking. I don't care as much about fancy restaurants- good coffee's enough for me. Our son wants outdoor activities, but nothing too hot unless he'll be out on the water. Our daughter wants resorts, good gluten-free food, and shows; she votes for big cities where there's entertainment. So how do we make this work? Honestly, most destinations have something for everyone if you plan it right. In Costa Rica, we did adventure activities, wildlife spotting, and especially for Ronnie, a cooking class in La Fortuna. Then we moved to a resort where Shoshana could relax by the pool and enjoy good meals while Jacob and I spent hours snorkeling and kayaking. The key is making sure everyone gets something they're excited about. Not every activity has to work for everyone, but you should all have activities that you're genuinely looking forward to. And sometimes that means compromising. I wasn't thrilled about spending days at a resort rather than trucking around doing more sightseeing, but the kids really appreciated it. So how do you make the final call? For us, it usually comes down to a combination of factors lights and hotels using points. Does it offer a good balance of activities everyone will enjoy? But also, are we excited to travel there? Here's the thing, you can't optimize everything. Each destination is gonna have some trade offs. When we went to Japan, we knew it would be a really long travel day. We also knew the kids were young for such a big cultural shift. Jacob was 12 and Shoshana was nine. But we were confident that it was an incredible opportunity and we felt ready for it. Plus the kids were beyond excited. And you know what? The first evening was really rough. Jacob had a total meltdown on our food tour. He was exhausted and overwhelmed, but by the next day after we'd all gotten some sleep, it was fine. Great, even. My point is this: don't wait for the perfect moment or the perfect destination. If a trip checks most of your boxes and you can make the logistics work, just book it. You'll learn more from actually traveling than endlessly planning the theoretical perfect trip. Alright, let's recap the process. Start with your constraints: school breaks, flight, logistics, kids' needs, points, availability. Then set up a simple spreadsheet to organize by timing. Do a weather reality check for your specific date. Look at flight route and award availability, early. Balance everyone's interest as best you can, and then just make a decision. Trust me, after you've done this a few times, it becomes almost automatic. You'll develop a sense for what works for your family and what doesn't. Next episode, we're gonna dive deep into Costa Rica with kids, what we did, where we stayed, and what we do differently. It was one of our favorite family destinations, and I'll give you all the details you need to plan your own trip. Until then, pull out a spreadsheet and start mapping out your next adventure. If you like this episode, be sure to leave us a review, plus share it with another friend who wants to plan more trips with their family.