A Honeymoon Stay on the Wrong Nights — Reader Mistake Story

Apr 12, 2019

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Today, I want to share a story from TPG reader Ryan, who misunderstood the terms of a Hilton free night certificate:

My fiancée and I are getting married on Oahu this summer and decided to take a short honeymoon to Maui, since we don’t have time for a longer vacation. We had both signed up for the Hilton Honors American Express Aspire Card, and thought we would use our free annual night to stay at the Grand Wailea, a Waldorf Astoria Resort on Maui. Nights at the Grand Wailea were running over $600 after resort fees and taxes, so we were excited to stay at a high-end resort and save much more than the $450 annual fee (see: rates & fees) for the Aspire card. However, we made some mistakes in our planning.

Our first mistake was to book our flight before booking our room at the Grand Wailea. Due to flight prices, we decided to catch a red-eye out of Maui on Saturday night, arriving back on the mainland on Sunday. That was a few hundred dollars cheaper than flying out on Sunday morning.

Our second mistake was that after booking our flight, we waited two days before we got around to booking the hotel. It was only then we realized the free night certificate on the Aspire card is only redeemable for weekend nights. Since we’re flying out on Saturday night, we can only use one of our free nights, meaning we have to either use another payment method or stay elsewhere for our first night. We were already outside the 24-hour cancellation period for our flights, so we couldn’t cancel or change our tickets without paying a fee.

We have not yet decided what we’ll do. We’re considering paying for an additional night at the Grand Wailea — we could use our $250 resort credit to help subsidize the cost of the hotel night, but we’d still be paying close to $400. Alternatively, we are considering trying to stay at another hotel and then move to the Grand Wailea for the one night. We hope others can learn from our mistakes.


Among the wide variety of stories I get from readers, the most common mistakes involve simply failing to read the fine print. Hilton free night certificates offered by the Aspire card (and others) are only valid on Friday, Saturday or Sunday nights. Amex clearly markets those free nights as “weekend night rewards” and defines which nights are eligible in the terms and conditions, so any expectation they could be redeemed on weeknights amounts to an oversight by Ryan and his fiancée. I point this out not to chastise them, but to illustrate how attention to detail can help you avoid similar pitfalls in your own travels.

There are a few bits of good news for Ryan and his fiancée if they decide to pay for a second night at the Grand Wailea. First, since they each have an Aspire card, they could split payment across the two cards at checkout and redeem both of their up to $250 resort credits for a total of $500 toward their stay. Second, they may be able to lower their out-of-pocket costs further with some of the current Amex Offers for Hilton stays, one of which is a $100 statement credit for spending $500 or more at Waldorf Astoria properties.

Finally, redeeming Aspire resort credits won’t prevent them from earning points. Between their bonus for Diamond status and the increased earning rate on the Aspire card, they can earn 34 points per dollar spent on their room rate, along with additional points depending on what sort of bonus promotion Hilton offers this summer. If they spend $500 on the room (not including taxes and fees), they’ll net at least 17,000 points — that should soften the blow of having to pay for the additional night.

I appreciate this story, and I hope it can help other readers avoid making the same mistake. In appreciation for sharing this experience (and for allowing me to post it online), I’m sending Ryan a $200 airline gift card to enjoy on future travels, and I’d like to do the same for you. Please email your own travel mistake stories to info@thepointsguy.com, and put “Reader Mistake Story” in the subject line. Tell us how things went wrong, and (where applicable) how you made them right. Offer any wisdom you gained from the experience, and explain what the rest of us can do to avoid the same pitfalls.

Feel free to also submit your best travel success stories. If your story is published in either case, I’ll send you a gift to jump-start your next adventure. Due to the volume of submissions, we can’t respond to each story individually, but we’ll be in touch if yours is selected. I look forward to hearing from you, and until then, I wish you a safe and mistake-free journey!

The information for the Hilton Aspire Amex card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Featured photo courtesy of Grand Wailea.

For rates and fees of the Hilton Amex Aspire Card, please click here.

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