The planning mistake that makes award travel harder than it has to be

Reading Time: 3 min

When most people plan a trip, they start by looking at the calendar and choosing their dates. After all, they have to think about weekends, how many workdays they'll need to take off, school schedules, and other commitments.

For years, that's how I planned trips, too. But when it comes to award travel, I've learned that starting with the dates isn't always the best approach.

One of the first things I learned about award travel is that having enough points doesn't guarantee you'll be able to book the trip you want. Availability is often the real challenge.

I'm seeing that firsthand with a family trip to Spain I'm planning for this summer. My ideal scenario was to leave on a Thursday or Friday and return the following Friday, so I could miss as few workdays as possible.

When I started searching, though, there was little to no award availability for five people on those dates. And when seats did become available, they cost two or three times as much as other options.

Once I expanded my search by a couple of days, award availability looked noticeably better. I found saver-level award space for all five of us by leaving on a Wednesday night, just one day before my ideal departure date, instead.

Sure, it means taking an extra day off work. But it also means getting my entire family on the same flights while saving tens of thousands of points compared to traveling on my original dates. If I had started with fixed dates and refused to budge, I probably would have ended up spending far more points or settling for a less convenient itinerary.

Over the years, I've learned that the best award trips usually start with whatever is hardest to book. For me, that usually means flights first, especially when I'm traveling with my family. Finding five award seats on the same flight at a reasonable price isn't always easy.

But it's not always about the flights. Sometimes the hotel — or even an Airbnb — becomes the deciding factor. There have been plenty of trips where the place we're staying is a focal part of the experience, whether it's a hotel I've wanted to visit for years or a unique Airbnb that would make the trip more memorable for my family.

Part of the fun of travel is staying somewhere you're genuinely excited about. If that property is only available on certain dates, I'd rather adjust the trip to fit those dates than settle for something else.

That's what I mean by working backward. I figure out what's worth planning around first, then build the rest of the trip from there.

In case you missed it...

​Your dream hotel might have hidden award nights

I've found that being flexible doesn't usually mean completely changing your plans. Sometimes it's as simple as leaving a day earlier, coming home a day later, or shifting your hotel stay by a night or two. Small changes can open up award space that wasn't available before.

I know work schedules, school calendars, and family commitments don't always leave much room for flexibility, but when they do, I've found that even small adjustments can make a bigger difference than having more points.

More often than not, that's what's helped me book the trips I really wanted.

This inexpensive tracking card grants peace of mind for travel documents

EPICKA's Wallet Tracker makes sure you never lose your wallet again with its full iOS compatibility. Just sync with Apple's "Find My" app and you can pinpoint your wallet's exact location.

Get it at Amazon