Home Points & Miles I Almost Fell Into One Of The Biggest Traps For Travel Hackers

I Almost Fell Into One Of The Biggest Traps For Travel Hackers

by joeheg

I’ve been planning a trip to Hawaii for almost 9 months. Once Sharon and I hammered out our dates for the trip, I went through my usual process. Start with the most challenging thing first and work from there.

That usually means starting with the flights. I was able to find award flights to/from Hawaii on Delta and Hawaiian. I then booked our inter-island flight on Southwest.

The next thing was finding places to stay. We’re breaking up our time on Kauai between two locations. The last part of the trip we’re going to Oahu. Plan A was to use our Disney Vacation Club points to stay at Aulani at Ko Olina. However, by the time I was looking, all the availability was gone for our dates. I went to Plan B and looked for a Marriott property in Honolulu.

We spent plenty of time looking at the various options considering the points we’d have to redeem to book the stay, the likelihood we’d be able to get an upgrade using our Platinum Suite Night Upgrades, and additional expenses including resort charges and parking fees.

I finally decided on a hotel, booked a base level room with points and applied our upgrade knowing we wouldn’t know until 5 nights before the stay if we’d get a better room. I was planning on asking for a paid upgrade if our certificates didn’t clear.

The trip is almost here so on a whim I checked to see if there were any available rooms at Aulani. One downside of putting a room on the waitlist with Disney as you have to pick a specific room type. While my choice was still booked, there was a different room view available.

I felt a moment of hesitation. I know this was my Plan A, but I convinced myself that I was OK with Plan B over time. The option that I spent hours researching, comparing options and finally picking the best one. In my mind, I convinced myself that this was the best choice. In a second, I would throw that all away and go somewhere else.

I went to Sharon and asked her what she wanted. She turned back to me and asked why I’d like to stay at Aulani instead of the hotel we booked. I effortlessly named five advantages over the second option. She gave me the “You know what to do” look, but I wanted her OK before ditching our plans for other ones.

Here’s the trap. When you book trips using points and miles, your number one choice may not be available when you’re planning the trip. Airlines might not release space in first class until a few days before the trip. Hotels can mess with availability to limit award bookings only to release space later. If you spend hours making other plans, it isn’t easy to throw all of that away and go with your first choice.

Learn to deal with it. You’re going to spend time researching flights or hotels that you’ll never see. Take it as a learning experience. Be happy that you could make a trip happen when you were faced with limited award space. The fact that you can upgrade your trip should make you happy, not sad.

We’ve all been there. Part of the fun of this game is the search. Enjoy your growth beyond looking for easy redemptions. You may need to use that knowledge for a future trip. Always be prepared to ditch your plans if you find something better.

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This post first appeared on Your Mileage May Vary


Steven January 15, 2022 - 7:21 pm

Availability versus money. It’s always about those two things with points and miles, you can have one or you can have the other hit you can’t have both. Points are money (we all know that) and when we redeem points we are essentially getting discounted and sometimes very discounted rates on properties and airfares that we might not otherwise be able to afford. That’s the essence of the points and miles game I suppose, and what makes it so damn enjoyable and addictive, the joy of getting something we couldn’t otherwise afford.

DaninMCI January 16, 2022 - 5:51 am

It sounds like you already fell into the trap of overthinking it. Most of us in this game or hobby enjoy the hunt as much as the actual stay so maybe that all worked well for you but many people overthink the awards and travel and make themselves miserable. This is a no win situation for you if overthink it. You either gave up on a cheaper Marriott award stay that you and invested so much time in or you didn’t get to book the Disney property you “really” wanted in the first place. Either way if something doesn’t go as planned or worse yet, goes badly. You’ll second guess yourself and your spouse could also lay blame. Personally on Oahu, anything you can do to stay away from Waikiki for more than a one night stay is worth it. The tourist and homeless stay overnight at Waikiki, those that are in the know, stay elsewhere.


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