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Checkin’ ‘Em Off: My Summer Travel and Points To-Do List

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Travel and Points Chores

Travel and Points Chores

I’ve enjoyed slowing down in the points and travel hobby since summer started.  While I’m  not going cold turkey, I’m ensuring the activities I’m taking on are worth my time.  And some of that has been ignored for too long.  Naturally, I like to focus on the fun stuff in our shared hobby, often ignoring the drudgery of certain travel and points chores.  Here are just a few I’m taking care of over the summer.

Mitigating Expiration

Fewer points and miles currencies expire these days.  And in many cases, we can easily avoid expiration with something simple, like shopping through a program’s portal.  But a few programs have stringent policies.  My biggest weakness here is with Wyndham Rewards.  Wyndham points expire at 18 months of inactivity (okay, easily avoidable) and four years after they posted to the account (eek).  Thanks to holding the legacy 2x everywhere Wyndham card and its 15k anniversary bonus, I avoid the former.  But the latter is an annual issue for us.  A simple transfer to Caesars Rewards and a subsequent move back to Wyndham solves that (annual limit is now 60k points).

We’re plenty busy with my American Airlines account, but not my wife’s, primarily due to my current Executive Platinum status.  A quick, small portal purchase pushed back my wife’s expiration date another 24 months.

And so it goes.  I’m working through each program where I have currency, revalidating expiration dates, and taking action, as needed.  Tedious, but it’s part of the deal.

Out with the Old, In With the New

I have a hot and cold relationship with paper.  I still rely on old-school paper statements, as I enjoy the simple, physical reminder to pay the bills.  Also, I hold on to certain documents which come with new cards, particularly rewards- and terms-related.  I organize all cards and related documentation in two large binders – one for bank point and cash back cards, the other for co-branded cards.  I keep certain cards long-term, but I otherwise play a high turnover game.

Needless to say, these binders need updating – adding the new stuff and tossing out the old.  I find the process not particularly satisfying, but I definitely enjoy the result.  Maybe you should try a credit card colonoscopy.  You’ll feel dynamite after.

Finishing Up Dell Credits Early

Dell brings on the drama.  That’s probably not news to anyone holding a Business Platinum card and trying to use its $200 biannual credit.  In past years, I’ve threaded the needle, holding off on purchases until an elevated portal payout is available.  But with Dell increasingly cancelling my orders on 2023’s front end, I tapered off that practice.  Indeed, I started the second half of this year with my first two orders via sales rep.  I didn’t earn portal rewards, but I didn’t care.  I just want to avoid order cancellation.

With increased Rakuten portal payouts over a recent weekend, I decided to experiment with my third order.  If my online attempt worked out, great.  If it didn’t, I’d go back to a sales rep.  It turns out the online order and portal rewards sailed through flawlessly.  Go figure.  I have one order left, and I plan to complete it by the end of July.

Travel Planning, and Some Booking

Fall is my favorite time of year to travel, and some of my favorite bands also like that season, apparently.  I’ve booked award flights and hotel stays for trips to see Sigur Ros, Explosions in the Sky, and U2.

I’m neither a huge planner nor a last minute traveler.  Beyond the next few months, nothing is in ink.  I need to finalize a few late 2023 and early 2024 plans, probably leveraging my American Airlines Executive Platinum status expiring early next year.  It’s great to have plenty of options, but it’s getting closer to decision time there.

Travel and Points Chores – Conclusion

That’s mostly it for the rest of the summer.  I know I must leave room for other projects as new points developments pop up.  We’re constantly faced with new angles, and hobbyists with the time and energy can largely come out on top.  Through it all, striking the right balance is key.  What’s on your to-do list this summer?

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Benjy Harmon
Benjy Harmon
Benjy focuses on the intersection of points, travel, and financial independence (FI). An experienced world traveler, husband, and father, he currently roams throughout the USA close to expense-free. Benjy enjoys helping others achieve their FI and travel goals.

Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. The expiration of the Choice Hotel program is difficult for me and now even worse since I have to move my Radisson points over.

    • Can’t drum up activity once every 18 months, Dan? I’m loving the WF Choice Select card for many reasons, and I won’t need to worry about expiration otherwise. But I know that’s not for everyone.


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