(Free Nights Awarded ) Why I paid over $1000 to upgrade 3 no-fee Hilton cards without a bonus offer

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Update 5/15 – I wanted to do a follow-up to this original post as there were some questions about whether not upgrading to the Aspire would trigger a free night award without having to wait for the next cardholder anniversary.

I upgraded all three cards at the same time at the end of March. All three of them had different anniversary dates, but were in the middle of the membership year (not just before the anniversary date). All of them received the resort credit immediately upon upgrading. All three of them were charged a pro-rated annual fee (ranging from $200ish-$400ish) in the statement period AFTER the statement period in which I upgraded. And we have now recieved three free night awards, 2-3 weeks after being charged the pro-rated annual fee and 6-7 weeks after upgrading.

American Express is famous for providing very lucrative targeted upgrade offers from the no-fee Hilton Honors card to the premium Hilton Surpass and the super-premium Hilton Aspire.  These upgrade offers usually occur after a no-fee card has been active for at least a year and will often provide 100,000-150,000 Hilton Honors points, but without a hard pull or a new account on a credit report.

Because of this, common procedure is to avoid cancelling an Aspire or Surpass and instead to downgrade them to the no-fee card.  After a year or so, there will frequently be upgrade offers to tempt you back.

My wife and I had three no-fee cards between us that were all over a year out from a downgrade.  I’ve been eyeing our accounts for awhile, waiting for that upgrade to appear.  But instead, I upgraded all three of them last week, paying 3 annual fees in the process…all without any bonus points on offer.  And I think it was a great decision.

a pool with lounge chairs and palm trees
Zemi Beach House, Anguilla

Details of Relevant Cards

Card Offer
160K Points + free night certificate ⓘ Non-Affiliate
160K after $6K spend in first 6 months. Free night certificate every year - first certificate is awarded 8-12 weeks after approval. Terms apply.
$550 Annual Fee
Information about this card has been collected independently by Frequent Miler. The issuer did not provide the details, nor is it responsible for their accuracy.
140K points ⓘ Non-Affiliate
140K after $3K spend in 6 months. Terms apply.
$150 Annual Fee
Information about this card has been collected independently by Frequent Miler. The issuer did not provide the details, nor is it responsible for their accuracy.
Recent better offer: 130K + free night certificate after $2K spend in 3 months [Expired 7/19/23]
130K Points ⓘ Affiliate
130K after $3K spend in 3 months. Terms apply.
$95 Annual Fee
90K after $2K spend in 6 months. Terms apply. (Rates & Fees)
No Annual Fee
Information about this card has been collected independently by Frequent Miler. The issuer did not provide the details, nor is it responsible for their accuracy.
Recent better offer: 70K + free night certificate after $2K spend in 3 months. [Expired 7/19/23]

Why we downgraded our Aspires

The Hilton Aspire might be the single best hotel card on the market and can be a revenue-positive annual proposition. As a refresher, here’s the schwag:

  • No foreign transaction fees
  • Hilton Diamond status
  • $250 Hilton Resort Credit per membership year.
  • $250 Airline Incidental Fee Credit per calendar year.
  • One Weekend Night Reward at almost any hotel or resort in the Hilton portfolio with your new card and each year of Card Membership (currently usable any night of the week).
  • Priority Pass
  • Annual Fee: $450

Assuming you can take advantage of the full value of the two credits, you’re $50 up each year, with a free night valuable up to 120,000 points each AND Diamond status (that never seems to go away, even after you downgrade the card). That’s a good deal.

So why did we downgrade both of our Aspires in the first place?  COVID, that’s why.  Amex has been great about extending the “weekend” night certs, but we ended up at the beginning of last year having seven certificates that we’d have to use throughout 2022 (and that’s not counting our Hyatt, Marriott and IHG certs). With no Hilton resort stays planned for last year, we decided to downgrade and wait for an upgrade offer sometime this year.

lunch at the new gwen's
Gwen’s Reggae Beach bar…a walk down the beach from Zemi.  Photo courtesy of Anguilla-beaches.com

Ok makes sense, but then you did what?!?

We’ve been wanting to spend some time on the Caribbean island of Anguilla for some time now and got much more interested when Zemi Beach House joined the Hilton Portfolio as an LXR property.  The resort is right on Anguilla’s dreamy Shoal Bay East and gets rave reviews.  It looks awesome.  Standard rooms start at 95,000 points per night, making it a perfect candidate for the Hilton Free Night cert.  The problem is that, traditionally, it’s difficult to find more than a couple standard nights in a row. It’s bit of a time gauntlet to get to the island, especially from the West Coast where we live, so a short stay isn’t desireable.

We were originally supposed to be at a conference in Germany the last week of March over my wife’s Spring Break, but that was postponed, leaving us with an open week.  And what would you know, Zemi Beach House was wide open.  We booked a 6-night stay using free night certs.

We’ll get free breakfast at the resort and there’s a plethora of fun beachside grills/bars to check out on the island, but I assumed that we’d want to eat at least once at the resort. Also, while we’re not big resort spa folks (primarily because of the often exhorbitant cost), the Thai House Spa looks pretty incredible.  What a perfect place to have a few hundred bucks of Aspire resort credit, right?  I thought so too.

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Thai House Spa at Zemi Beach House. Photo courtesy of elitetraveler.com

But wait. We have a lot of math-aware folks who read this site and all of them are saying…you spent $1350 to upgrade three cards in order to get $750 of resort credit?  What kind of fool are you?  Well, a big one, but that’s another story…

Here’s my reasoning:

  • I can always use the full value of the airline credits by paying a seat fee to upgrade cheap Alaska tickets (without logging into my account).  After 24 hours (so the charge isn’t refunded to the card), I can log in to my account, cancel the ticket for no fee and place the entire balance in my Alaska wallet for future travel.  The airline credits reset on the calendar year, so I’ll get a total of $1500 in Alaska credit before I have to pay another annual fee.
  • Stephen (who saves us all money) confirmed that when he upgraded his no-fee HH card to the Aspire last year, he got a free night on the front end and another one on his first anniversary.  After researching it, I found that others have found this to be the case as well.  I dont know whether or not this is official policy and so it could end at any time.  But it seems as though, even without a points bonus, upgrading to the Aspire triggers an immediate free night cert.
  • Officially you can’t keep your anniversary free night if you downgrade to a no-fee card, but in practice if you wait for it to deposit into your Hilton account and then downgrade, it will stay there.  Since Amex will prorate annual fees throughout the year (as opposed to the 30 or 60 day limit on most issuers), it might cost an extra $30-50 dollars depending on how quickly the cert is deposited.  But you’ll have a free cert valid almost anywhere.

So, in the first year, for my $1350-$1500 investment I’m expecting:

  • $1500 in Alaska wallet funds
  • $750 in credit at Zemi Beach House
  • 6 Free Night certs good for up to 120,000 points each (completely replenishing what we used for Zemi, but valid until into 2023)

It felt a little yucky to have to waste the opportunity at an incentivized upgrade.  That said, the bird-in-the-hand of 6 certs and $750 to spend (at a resort that we’re going to be at already) seemed too good to pass up.

a man standing on a beach with a straw hat and sunglasses
Nick at the Conrad Bora Bora…one of his favorite places to burn a Hilton free night cert

Final Thoughts

I wanted to talk through this whole process as a follow-up to my earlier posts about trying to tailor our points and miles earning/burning towards both enjoyment and value…and how personal a proposition that is. (See The Myth of One Size Fits All and Chase Sapphire Reserve: Why .25 cents is worth $250 (for me)).

This was another example in which I hesitated to make decisions that ran counter to how I perceived “conventional wisdom.” Burning 6 free night certs when I could utilize a 5th Night Free and one cert and upgrading the no-fee Hilton cards to the Aspire without waiting for a bonus points offer aren’t intuitive for me. I think it’s undoubtedly the right call in this situation, but I really had to think through it, as my first impulse was to say, “no way.” I don’t think everyone should run out and upgrade their no-annual fee Hilton cards without a good reason.  But, for me, the immediate utility outweighed the theoretical future value of a possible points upgrade.

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