Gaming out my Waldorf Astoria stay

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As I wrote last month, this January I’m heading to Maui for what I’m expecting to be an unusually-for-me expensive vacation, so I’ve spent some time in the past few weeks gaming out what the options are to save money on the trip without annoying my partner too much along the way.

Shorter car rental

Since we plan to drive around and explore Maui, I had initially planned to rent a car at the airport and drive to the Grand Wailea. I quickly realized this made no sense: not only would I pay for 5 days of car rental, but I’d also pay for five days of valet parking, since the Grand Wailea doesn’t have a self-park option.

By taking a cab or shuttle from and to the airport, I’ll save on both daily rental costs and daily valet parking: a roundtrip shuttle for two from the Grand Wailea’s preferred vendor costs just $99, and I may be able to shop around to bring that down even lower.

Amex Offer of $70 off $350

I was targeted for the current Amex Offer of $70 off $350 spent at “Waldorf Astoria Hotels & Resorts in the US, Amsterdam, Berlin, Edinburgh, and Paris; and, Conrad Hotels & Resorts in the US.” While such promotions sometimes exclude Hawaii, this one doesn’t seem to, so I’ll use my Hilton Ascend American Express card to check in and put the first $350 of room charges on that card.

As I wrote in my original post, the Grand Wailea currently claims to give a $15 per person daily in-room dining credit as their Diamond breakfast benefit. Readers quickly pointed out in the comments that with a $7 delivery charge and 20% fixed gratuity, that works out to about $19 in actual food if you’re trying to spend the exact amount of the credit.

Instead of trying to game the room service menu to spend exactly $19 per day, I figure we’ll just order what we want and let the excess count towards the $350 threshold for my Amex Offer.

Hilton Honors American Express Aspire Card Referral

Thanks to American Express’s “universal referral” system, I can refer my partner to an Aspire card despite not having one myself (you can find my universal referral links on the Support the Site! page). I’ve written about it before, but it’s worth spelling out again just how good this deal is:

  • I receive 20,000 Hilton Honors points for referring my partner;

  • My partner receives 150,000 Hilton Honors points after spending $4,000 within 3 months;

  • My partner gets a $250 airline fee credit in 2018 and another $250 airline fee credit in 2019;

  • We already have an eligible stay planned where we’ll be able to use the $250 Hilton Resort statement credit (a cardmember year, not calendar year, benefit);

  • And she’ll get an unlimited Priority Pass membership that allows up to 2 guests, so if I ask nicely she might take me with her into lounges when we travel.

182,000 Hilton Honors points (after earning 3 points per dollar on $4,000 in spend) are over half the points cost of our stay at the Grand Wailea, which I jokingly valued at $8,500 but realistically value at around $2,000. Valuing the airline and resort statement credits at half of face value, this works out to roughly $1,375.

I don’t like paying $450 annual fees. I’ve never paid a $450 annual fee. But this is a no-brainer for us since we already have a stay at an eligible resort booked.

Conclusion

There is one interesting question you might have after reading this: my Ascend card will get a 20% discount on exactly $350 in spend, while my partner’s Aspire card will get a 100% discount on up to $250 in spend, so which card should the first Grand Wailea room charges go on, and which card should be the backup?

In part, the answer is that we don’t have to decide until we know the final room charge. If it’s less than $350, we’ll put the entire charge on the Aspire card and get $250 back. If it’s more than $600, we’ll put $350 on the Ascend and the remainder on the Aspire, maximizing both opportunities (and the higher Hilton earning rate on the Aspire).

But for final charges between $350 and $600, what’s the right order to place the charges in? I think my preference is to put $350 on the Ascend and receive $70 back, then put the remainder on the Aspire, because the remaining cardmember year Aspire credit will remain available for later use.

But there’s a good argument, an argument I might even agree with depending on the day, that the Aspire resort credit is available at such a limited footprint of properties that maximizing that credit when we do have the opportunity is a much higher priority than triggering a piddling 20% discount, the kind of discount I can beat 365 days a year through manufactured spend.

Sound off in the comments if you feel strongly about it one way or the other.