Flight-First vs. Destination-First: Which Travel Planning Method Works Best for You?

When it comes to traveling with a family (especially a party of five like mine!), using points and miles is a total game-changer. But here’s something most people overlook: how you plan your trip makes a huge difference in how far those rewards stretch.

Two popular approaches are the Flight-First Method and the Destination-First Method—and I’ve used both plenty of times. Let me walk you through what they are, and share how each one has worked for us in real life.

✈️ The Flight-First Method

This is the MVP of travel hacking—and honestly, it’s how I’ve booked most of our family trips on points.

What it means:

Instead of choosing a destination first, you start by looking at where your points or miles can take you for the best value—then plan your trip around that.

Pros:

• Saves serious points or cash.

• Works well for big families since you can snag multiple award seats.

• Great for bucket-list trips without the bucket-list price tag.

Personal example:

When I was planning out our 2024 family trips, I was perusing Google Flights (one of my favorite tools to use) searching for a trip that my family could take over my kids’ summer break. Google Flights allows you to search from your home airport (or any airport) to anywhere. This is such a cool feature. Since we live in eastern Pennsylvania, we are willing to position to JFK for the best flight deals, so I often look there when flying internationally.

To get the best results you can leave the dates open. But if you’re looking for something in the next 6 months, you can filter your results once the map pops up. From there you can see where you can fly to (in my case from JFK) and how much it would be for 1 week. If you’re flexible, you can score some pretty great deals.

I ended up finding a flight from New York City to St. Thomas for around $300 round trip. We had never been there, so I thought why not explore a new island? I then found that exact itinerary in my Capital One Travel Portal and booked the flight for 30,000 points round trip each for the 5 of us plus our nanny. I didn’t worry about transferring points or anything. I just booked with the points we had straight from our Venture X card. Did I love saving $1,800 in flights? I sure did!

📍 The Destination-First Method

This is the more traditional route—you know where you want to go, and you work backward to find flights that fit your schedule and budget.

What it means:

This works best when the destination is non-negotiable. Maybe it’s a family wedding, a dream destination you’ve had pinned for years, or the kids are set on meeting Mickey Mouse this summer.

Pros:

• Perfect for bucket-list or milestone trips.
• Good if you’re willing to pay more in points or be flexible with flights/hotels.

Personal example:

Our oldest daughter was begging us to take her to a Taylor Swift concert last year. At first we said no, but after giving it some thought, we decided why not just look into it and see if we can create a memorable experience for her. Taylor Swift tickets in Europe were cheaper than in the U.S. and if we had to fly anyways, why not go somewhere really cool? After researching the cheapest European city to see T.S. we found London to be the most affordable, and easiest to get to. The concert date was set of course and I knew that I wasn’t going to have much flexibility on my side when booking flights. But I ended up finding tickets from JFK to LHR for about 45,000 each round trip in August with dates that would work for us through the Capital One Travel Portal.

Is that the best redemption? No. It was a lot, especially for 2 people. But I was willing to let go of the points because of the set concert date and for making the memories. Looking back, I should have seen if I could have gotten a better redemption by transferring points out of the portal and into a partner airline to book with less points. But at that time in my points and miles journey, I hadn’t gotten there yet, so that’s okay! We ended up having such a fun getaway to London and those memories from that Mama/daughter trip will last forever.

Final Thoughts

If you’re just getting started with travel rewards, start with the Flight-First Method. It’s the best way to see immediate savings and get a feel for how powerful points and miles can be. But for those “this-is-the-year-we-go-to-Italy” trips, the Destination-First Method still has its place—you’ll just want to plan early and stay flexible.

At Points to Passports, I’m here to help you use points and miles to make more travel possible—whether you’re chasing flight deals or lifelong dreams. And if you ever need help finding those deals or choosing the right cards to earn the most points, I’d be happy to talk you through it!