Advertiser Disclosure: The Rewards Mom has partnered with CardRatings for our coverage of credit card products. The Rewards Mom and CardRatings may receive a commission from card issuers.
A few years ago, if you had asked me whether it was worth traveling over school breaks, I would’ve laughed and said, “Only if we win the lottery.”
Because as someone who has worked in the travel industry for most of my adult life—first as a travel agent, then for an airline—I knew the golden rule of getting a good deal: Travel off-peak. That’s where the savings were. That’s where the wide-open seats, low hotel rates, and promo codes lived.
But when our kids got older, everything changed.
If you’re just getting started with using points for family travel, this free beginner’s guide walks you through how we began—and how you can, too.
Why Off-Peak Travel Stopped Working for Us
As much as I loved the idea of sneaking away in September or planning a quiet January getaway, it got increasingly hard to make it work.
Our kids are in dual-language immersion programs. They play competitive sports. And when they fall behind in school, there isn’t much we can do to help with Chinese grammar or missed algebra.
Pulling them out started to feel more stressful than relaxing.
But when I looked at traveling over spring break, fall break, or heaven help us—Christmas? Prices were often two to four times higher than what I’d find in the off-season. Flights that cost 18,000 points the beginning of October were 62,000 points in December. Hotels that were $200 a night shot up to $600.
We were stuck. Until we weren’t.
What Working for an Airline Taught Me
When I worked for JetBlue, I used to answer calls from people trying to redeem their credit card points. And I’ll be honest—I was skeptical. Actually, I was judgmental.
I assumed they had saved up for years or were spending thousands of dollars a month. I also thought it was irresponsible to need multiple credit cards to pay for one flight.
Meanwhile, I had been using one airline card for 15 years. Want to guess what that earned me?
One round-trip flight to California for our family of six. That’s it.
But what I didn’t know then is something I talk about all the time now: Why you never have enough miles—and how transferable points solve that problem.
The Shift That Changed Everything
Eventually, I got curious. I started listening to those callers, learning how they were using their points, and realizing just how far behind I was.
I didn’t know that credit card points could be transferred to different travel partners. I didn’t know what an award chart was. And I had no idea that some redemptions were fixed, meaning even during peak travel times, the points cost didn’t skyrocket with cash prices.
If you’ve never transferred points before or aren’t sure how it works, this guide breaks it down.
So instead of paying $1 million points for a Christmas week hotel in Mexico, I booked two rooms at an all-inclusive—one for my husband and me, one for the kids—for just 35,000 points each per night. Food included. It felt like cheating- in the best way.
Why School Break Travel Makes More Sense Now
With points, we could finally travel when it actually worked for our family.
Yes, flights and hotels over breaks are still more expensive in dollars, but we’re not using dollars anymore. We’re using a mix of transferable points, free night certificates, and a few other strategies (like shopping portals—here’s how I double-dip points through Rakuten).
Now, we plan most of our trips around the school calendar. Fall break. Spring break. Summer. Winter. We’re not scrambling to coordinate makeup work or checking their online school portal from a hotel room anymore. We just go.
If you’re someone who’s been waiting until “the kids are older” or “flights drop in price,” I can’t say this enough: the magic isn’t in the timing. It’s in the strategy.
What I’d Tell You If We Were Sitting on the Sidelines Together
You don’t have to wait until retirement. You don’t need to spend $30,000 a year. And no, you don’t have to settle for motel rooms off the highway while everyone else posts photos from beachfront resorts.
It all starts with the right kind of points and a plan.
If you’re ready to stop saying no to school break travel, here are a few posts that can help you get started:
- How to start using points and miles
- How to choose the best card for your goals
- How we booked a $14K Cancun vacation over winter break—almost entirely on points
- How to book Hyatt stays with points for families of 5+
And if you’re wondering which cards I recommend for earning flexible travel points, this list is a great place to start.
If you’re not sure where to start, grab my free beginner guide here. I made it for moms just like us—who want to travel more, even when the school calendar says no.
And if you’re not already following along, I’d love to have you in my community:
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→ Facebook group
Editorial Disclosure: Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Advertiser Disclosure: The Rewards Mom has partnered with CardRatings for our coverage of credit card products. The Rewards Mom and CardRatings may receive a commission from card issuers.
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Why We Stopped Saying No to School Break Travel