Just Add Some Wacky – The Importance of Creatively Redeeming Points and Miles

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Points and Miles Redemptions

The Importance of Creative Points and Miles Redemptions

I’m not a particularly creative individual.  I have my moments, but probably no more than the “normal” person.  One challenge in our hobby is inventively earning and redeeming various rewards currencies.  By doing so, we can potentially gain more benefits at higher volume than with straightforward plays.  And with ever-devaluing rewards currencies, the responsibility is on us to find novel methods for award redemptions.  Today, I’m describing three creative points and miles redemptions I’ve pulled off and their unique importance in my situation.

Disney World – From Expensive to “Free”

Years ago, my wife and I loved our Club Carlson Visa cards and the related benefits, as did many others.  For those who may not know, Club Carlson is a previous iteration of the Radisson Rewards program.  Cardholders could obtain the last night free on any multi-night award redemption.  We could easily maximize this benefit on two night stays, effectively cutting in half the required points per night.  Sadly but predictably, Club Carlson removed this benefit in 2015.  This was our favorite benefit with Club Carlson, and we were subsequently stuck with tons of devalued points.

We had no foreseeable use for these points at Club Carlson.  However, we were in the early stages of planning our first family vacation to Disney World.  We didn’t accept the common notion of “Disney World is expensive – deal with it”; we were looking for ways to deeply discount the trip.

The Alternative

In exploring redemption options, I noticed that I could redeem Club Carlson points for a variety of gift cards, including Target.  At the time, I knew that I could buy Disney gift cards with Target gift cards.  My wife and I zeroed out our entire Club Carlson balances on these redemptions.  I don’t recall the exact valuation we received, but I definitely remember that we got less cent per point value from this redemption than we would have from staying in Club Carlson properties.

But the value for staying at a Club Carlson property was a mirage.  In reality, we had no need for Club Carlson stays; we did have a goal of a cheap (or free, as it turned out) Disney World vacation.  In those terms, we got great value from this redemption, since we met our highest-priority goal.  I wouldn’t accept points and miles valuation groupthink.  I redeemed in what some may consider a subpar fashion, but it worked out great for us.

Points and Miles Redemptions
Be Our Guest Restaurant. Source: Walt Disney World.


Last year, Citi gave us plenty of warning on a key devaluation of the Citi Premier Card.  Citi removed the extra 25% value on ThankYou Points redemptions via their travel portal, including Cruise and Tours redemptions.  We had enjoyed booking Disney World resorts and tickets at a 1.25 cents per point valuation via Cruise and Tours for years.

Meanwhile, the crew over at GCGalore/Frequent Miler collectively discovered that ThankYou Points could be redeemed via Shop Your Way at a 1.2 cpp valuation.  I was immediately excited.  Shop Your Way members could redeem for a variety of gift cards, including Walmart, and I knew Walmart gift cards were tremendously useful for me (at the time).  How did my play work?

Citi ThankYou Points -> Shop Your Way Points -> Walmart Gift Cards -> Discounted Disney Gift Cards at Sam’s Club

Long story short, I obtained a large amount of Disney gift cards at a value of just over 1.25 cents per ThankYou Point (incorporating Sam’s Club discounts).  Was that substantial effort to obtain pretty much the same valuation I could obtain from Cruise and Tours?  Yes, but with one huge, significant improvement: I locked in a more flexible, long term 1.25 cpp redemption for our future Disney World vacations.  First, I broke free of the April 2021 death of the extra 25% point value.  Second, I wasn’t forced to use my ThankYou Points on Disney reservations that were and continue to be tremendously uncertain, due to the pandemic.

An Ugly Death

This play later died from multiple angles.  Walmart gift cards periodically disappeared from Shop Your Way.  Shop Your Way devalued the transfer rate to 1 cpp.  Sam’s Club quit accepting my Walmart gift cards as payment for Disney gift cards.  And after the Premier devaluation, Citi enabled easy 1 cpp cashout redemptions via the Premier.  I’m still glad I locked in that 1.25 cpp valuation with Disney gift cards, though.  We love Disney World and enjoy the flexibility that this redemption enabled.

Points and Miles Redemptions

Future Travel with a Beloved, Niche Currency

After the deaths of the ThankYou redemptions I mentioned above, I started searching for new ways of redeeming those points.  Once I refreshed my memory on Citi’s transfer partners, it clicked.  JetBlue!  In the past, I had exchanged JetBlue Points for Amtrak Guest Rewards points at a 2:1 ratio.  I decided to do the same with Citi ThankYou Points by transferring them to JetBlue, then on to Amtrak.

I love traveling on Amtrak, and I’ve continually obtained ~2.9 cpp on those redemptions.  That’s a 1.45 cpp valuation if I were to redeem on Amtrak travel immediately.  Sure, we have healthy Amtrak point balances currently, but given our preference of redeeming on sleeper cabins, we use them in large chunks.  The need to replenish our Amtrak balances is inevitable.  (This Points.com redemption is capped at 50k JetBlue points annually.)

The 1 cpp cashout via Premier showed up subsequently.  Given my current ability to earn ThankYou Points at volume, I plan to continue maxing out this Points.com redemption in addition to cashing out.  While Amtrak has solid credit cards and welcome offers, it’s a bit more difficult to substantially increase one’s points balance compared to the big airline programs with direct transfers from bank point currencies.

Creative Points and Miles Redemptions – Conclusion

Some may find the above plays unnecessarily convoluted.  Others may have absolutely zero interest in Disney World or Amtrak.  But I think a large portion of hobbyists enjoy more flexible and free travel options.  Therefore, I encourage all of you to search for more creative points and miles redemptions.  Start with your own goals and ignore the noise from others.  The search is part of the fun!

How have you inventively redeemed points and miles in the past?

Benjy Harmon
Benjy is a fan of points, miles, and financial independence (FI). An experienced world traveler, husband, and father, he currently focuses on roaming throughout the USA for close to free. He enjoys helping others achieve their FI and travel goals.

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  1. I have Amtrak booked next spring from Seattle to Chicago on the same line the train derailed. We booked a family cabin that has alot of room for a couple for about the same as a roomette. You get all your meals free, nothing great, but OK and you can bring wine in your luggage. I do enjoy the slower way of travel.

    • Byron,
      I’ve been on that same route, the Empire Builder, as well. A great experience! Well done getting the family room – we’ve primarily done the regular bedroom and roomette. Our one family bedroom experience was on the Auto Train, and we enjoyed that, as well. In my opinion, the Amtrak dining car fare is better than US airlines’ first class offerings, but I know that’s not saying much. Enjoy the Empire Builder!


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