Family Travel Unpacked: Make the Most of Travel With Kids

The Secret Weapon Hiding on Your School's Website

Melissa Conn Season 1 Episode 2

Discover how to book award travel with kids by checking next year's school calendar NOW. Learn why planning 10-12 months ahead unlocks the best points and miles redemptions for family trips.

Host Melissa shares the one strategy that changed her family travel game: using next year's school district calendar to book award flights and hotels before availability disappears. Perfect for families wanting to travel on points without breaking the bank.

In this episode:

  • Why your school's website holds the key to better award bookings
  • How to book speculatively with cancellable point reservations
  • Real example: booking Costa Rica with maximum flexibility
  • When to start searching for award availability
  • How early planning helps coordinate family schedules and PTO

00:00 Introduction to Quick Tip Tuesday

00:15 The Hidden Gem on Your School's Website

00:58 Why Early Planning is Crucial

02:01 Real-Life Example: Costa Rica Spring Break

03:16 Flexibility and Contingency Planning

04:04 Challenge and Action Steps

04:50 Conclusion and Final Thoughts

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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Hey there, travel planning parents. Welcome to Family Travel unpacked. I'm Melissa and you're listening to Quick Tip Tuesday. Today I wanna share what might be the single most valuable tip for booking family travel on a budget, or with points and miles. And here's the thing, it's probably already sitting on your school district's website right now, and you don't even know it. So picture this, it's October and you are thinking about spring break. Maybe summer vacation. You hop onto your school's website, download this year's calendar, circle the breaks, and start dreaming about where to go. Sound familiar? But here's what most parents don't realize. Your school district has probably already published next year's calendar, as in the 26-27 calendar right now, just sitting there on the website, our district posts the next year's calendar ridiculously far in advance. And once I discovered this? Total game changer. Here's why this matters so much for us: When we're booking with points and miles to stretch our family's travel budget, availability is everything. The best award seats, the ones that'll get your family to Europe or Hawaii or wherever without spending a fortune in cash, those disappear fast. We're talking 10 to 12 months out, sometimes even earlier, for popular routes during peak times. The same goes for hotel rooms that can actually accommodate the whole family at discounted rates. Our favorite brand, Hyatt opens their booking calendar 13 months in advance, and sometimes the award rooms that are big enough for a family get booked up within the first few days that it's open. So when I know that spring break 2027 is March 15th through the 19th, I can start searching for flights the moment that award calendar opens up. While other families are still looking at this year's calendar, I'm already locking in next year's trips. And listen, I'm not talking about some rigid, you have to book exactly 330 days in advance thing, but knowing those dates early gives you options, real options. Lemme give you a concrete example. When we decided to spend spring break in Costa Rica, I knew we'd want a few days at the Andaz Papagayo, since I'd only heard amazing things. But that property is incredibly popular in March, like it was a hundred percent sold out when we were there. Because I had downloaded the following school year's calendar as soon as it became available, I already had a pretty good idea of the dates we'd want to stay there, and I was able to lock them in 13 months beforehand. Now, here's the beautiful part about booking this early with points. A lot of award bookings are completely cancellable The points just go back into your account, so I could book speculatively. Ultimately, I had to shift things by a day, but it was a lot less stressful looking for one day of availability than if I'd had to look for all four days that late in the game. I did the same thing with our flights. I grabbed what I thought would be the right itinerary the day it became available. In the end, I had to shift it by a day, but it only cost me the fare difference in points. No biggie. And if your partner needs to request PTO, or if you need to coordinate with grandparents who might join you, having those dates locked down early makes everything so much smoother. There's plenty of time to get everyone on the same page. Now I can hear some of you thinking, but Melissa, what if things change? What if school suddenly shifts a break? Okay, fair. It's rare, but it happens. That's why booking with points is so perfect for this. You're not usually locked in. If the dates shift and you've already booked flights, you can usually cancel and rebook without a penalty if it's a US-based carrier; you are out maybe five minutes a time. That's it. Obviously, check the cancellation policy before you book to make sure that you're keeping flexibility. The upside is so much bigger than the risk. Because here's what happens if you don't book early: you're looking at slim pickings. Maybe there's no award availability at all, or you're paying cash prices that make you wince, or you're connecting through three cities because the direct flights are gone, or they're way outta your budget. So here's my challenge to you: after you finish listening to this episode, go to your school district website, poke around and look for the calendars page. I bet you'll find next year's calendar sitting right there, just waiting for you. Download it, circle those breaks, and then this is the important part: actually use that information. Don't just file it away. Open up your airline accounts. Check when the award calendars open, and set yourself a reminder. Also start talking with your family about where to go next school year because the family's getting those amazing point redemption trips. The ones flying their kids to Europe in business class for barely any out-of-pocket cost. They're not just lucky. They're usually planning ahead, and now you have the secret weapon to do exactly the same thing. Thanks for listening to family Travel unpacked. If this tip helped you share it with another parent who's trying to make travel work for their family, and if you've got questions about traveling with your kids using points and miles, reach out. I love hearing from you. Until next time, happy planning!