How to Plan an Entire Year of Family Travel in Under an Hour (Without More Cards or More Stress)

 If reward travel has ever felt confusing or like you’re “doing everything right” but still not actually taking trips, this article walks through the shift that changes everything. Using two example families, it explains how intentional planning — not more income or more points — allows families to turn everyday spending into a full year of meaningful travel. You’ll learn the exact system used to plan trips strategically, leverage flexibility, and create repeatable travel without overwhelm or extremes.

Most families don’t need more income, more credit cards, or more points. What they need is intention. This is the exact system I use to plan a full year of meaningful travel for my family of six—and once you see it, travel stops feeling complicated and starts feeling inevitable.

In this series, I walk through a simple but powerful framework using two fictional families. Family A is responsible, puts everything on a debit card, and pays cash for travel when they can. Family B is also responsible—but they route their existing spending through strategic travel reward cards, pay them off monthly, and earn enough points to take their family of five or six on at least one amazing (often international) trip every single year. Same income. Same expenses. Completely different outcomes.

The Simple Shift Most Families Miss

The biggest mistake I see isn’t choosing the wrong flight or hotel—it’s accumulating points without a plan to actually use them. Families stockpile points, feel overwhelmed by options, and either never book the trip or cash them in for one flight and call it done. Once you understand how to reverse-engineer travel before you search, everything changes.

This system isn’t about extremes or credit card churning. It’s about building a repeatable lifestyle of travel that opens the world for your kids year after year.

Step 1: Dream First, Strategy Second

Before opening Google Flights or any reward search tool, start with dreaming. I grab a Google Doc or my journal and ask questions like:

• Where would our family love to go this year?

• Is there a place I want to take my husband for a couples’ trip?

• Is there a milestone birthday coming up for one of my kids?

• What kind of summer memories do I want us to have?

Write down locations only—no prices, no logistics yet. This step matters because strategy works best when it’s serving a clear vision.

Step 2: Map Your Real Life on the Calendar

Next, I open Google Calendar and map out:

• Summer break

• Winter break

• Fall and spring breaks

• Long weekends and school holidays

For larger families, summer is often the easiest place to find flexibility, but don’t overlook short breaks. Even a weekend trip can turn into a meaningful memory. Last winter break, we flew to Las Vegas, went ziplining, and saw a Cirque du Soleil show—and that trip helped generate points for the next reward flight. This is how travel compounds.

Step 3: Add Strategic Mini Getaways

Not every trip needs to be international. I like to layer in:

• Drivable destinations

• One- or two-night hotel stays

• “Stationcation” weekends close to home

If you’re in Salt Lake City, that might look like Denver or Los Angeles. These trips don’t require many points, but they dramatically increase quality time and keep travel feeling normal and accessible for your kids.

Step 4: Search Flights First, Hotels Second

When it’s time to get tactical, I always search flights first, then hotels. Flights are more volatile; hotels are usually more stable.

My go-to free tools:

• Seats.aero

• Point.me

• MaxMyPoint (for hotels)

Flexibility here is everything. Especially with family travel, flexibility isn’t chaos—it’s strategy. Shifting dates by even one or two days can completely change how far your points go.

Step 5: Reverse-Engineer the Best Dates

Instead of forcing trips into rigid dates, I plug in destinations and scan within my available windows to see when points stretch the furthest. This lets me reverse-engineer the calendar in a way that feels simple instead of overwhelming.

Step 6: Leverage Transfer Bonuses (When They Make Sense)

This is where the magic happens. Inside your credit card portal, you can often transfer points to airline or hotel partners—and sometimes those transfers come with bonuses.

For example, I recently booked flights for all six of us to London:

• Retail cost: extremely high

• Points cost: 6,000 points per person

• With a 40% transfer bonus, the real cost dropped even further

Transfer bonuses aren’t always available, so timing matters. When they do appear, booking within that window can dramatically multiply your points. This is strategic—but not advanced. Anyone can do this once they know where to look.

Step 7: Sanity-Check Every Booking with a Reward Calculator

Before I book anything, I run it through my reward calculator. I plug in:

• Retail cost

• Points required

• Taxes and fees

The calculator instantly tells me if it’s a bad, good, or great redemption. I treat this as insurance—so I know I’m not wasting points or second-guessing myself later. It saves time and removes emotional decision-making.

Where Most People Freeze—and How to Fix It

This is the point where most families stop. Not because it’s hard—but because it feels like too many moving pieces. That’s exactly why I created my Reward Travel Starter System. It lays out this entire process step by step, including:

• My top credit card recommendations

• A done-for-you planner

• The reward calculator

• Insider strategies for flights, hotels, excursions, rental cars, and more

Everything covered in THIS YouTube playlist lives inside that system so you can repeat this year after year without starting from scratch.

Final Thought

This isn’t about one free flight or one lucky deal. It’s about creating a system that funds memories, expands your kids’ worldview, and makes travel part of your family’s normal rhythm of life. Once you see how this works, you can’t unsee it—and planning a full year of trips becomes something you can do in under an hour.