How I did on the American Express Hilton Aspire card

I wrote previously about using the American Express Hilton Aspire card to cover most of the cost of my honeymoon in Hawaii at the Grand Wailea, A Waldorf Astoria Resort. Since I cancelled the card as planned earlier this year, I thought I’d give a rundown of the total value proposition I ultimately got from it.

Signup bonus

For signing up for the card using my referral link, my partner received 150,000 Hilton Honors points and I received another 20,000 (we also got another 12,000 from meeting the minimum spend requirement for the card, but that’s less than I’d earn putting the spend on my own Hilton Surpass card, so we can set that aside). Hilton now allows you to easily and (relatively) quickly combine points from multiple accounts, so we pooled those points to pay for about 45% of our five-night stay, which I value at $1,900 (half a cent per point).

Total value: $855

Free night certificate

The Hilton Aspire card also comes with a free weekend night certificate on approval. To be honest, we did so much traveling in 2019 that I don’t remember which specific night we redeemed this award for, but since we typically stay in 40,000-point-per-night properties, I’ll assume we redeemed the certificate for “about” 40,000 points.

Total value: $200

Resort credit

If you’re a travel hacking junkie you may have recently read that American Express was issuing $250 resort credits to folks who had not completed eligible resort stays in 2020. There seems to be some confusion over exactly what’s going on, but this wasn’t news to me: after completing our stay in early January, 2019, our $250 resort credit posted automatically a week or two later. Then, in roughly April of 2019, a second $250 credit posted without explanation.

The most obvious explanation to me is that since the card was launched so recently, there were some early coding errors which kept some resort credits from posting automatically. When they discovered the error, American Express then manually applied an additional $250 credit to all accounts that had eligible resort activity, whether or not they had received an automatic credit.

I value the first, correct $250 resort credit at about $125 (we wouldn’t have run up the charges we did if they weren’t going to be reimbursed), and the second, incorrect credit at full value.

Total value: $375

Airline fee credits

If all the above makes it sound like I’m bragging, here’s the part where I prove that’s not true: I blew it on maximizing the card’s airline fee credits. The plan was to receive 3 years’ worth of airline fee credits while paying a single annual fee: in late 2018, in 2019, and in early 2019 before cancelling the card.

2018 went according to plan: we received the card in late 2018, quickly designated American Airlines as our airline, and bought 2 $100 electronic gift cards. The credits posted quickly, but we forfeited the remaining $50 in credits. Fortunately, the cards were used for flights my partner would have otherwise paid cash for, so I assign them the full $200 in value.

The right move in 2019 would have been to immediately buy another $200 in cards. But with our January travel, it just didn’t happen, and then I saw reports that gift cards had stopped triggering credits. Other options (JetBlue pet fees, etc.) still worked, but that would have involved switching the designated airline, learning the new technique, and monitoring the account all over again. So I did…nothing. We used the card for a few American Airlines checked bag fees in 2019, but I believe we received a total of $40 in 2019 credits.

For much the same reason, 2020 was a complete write-off, before we cancelled the card in late January.

Total value: $240

Unlimited Priority Pass membership

This is definitely the benefit that I was most surprised by: it turns out there are a lot of Priority Pass lounges! One issue when you have free lounge passes, whether through elite status, SkyBonus redemptions, or the 10 annual visits through the American Express Hilton Surpass card is that you constantly have to weigh whether you’re going to be laid over in an airport long enough to justify burning one of your lounge passes.

But with an unlimited membership, you can just pop in for some celery sticks or cheese cubes; it’s kind of an awesome feeling. It’s hard to put a value on something you would never pay for, but in a heavy travel year like 2019, an unlimited Priority Pass membership was very conservatively worth $100 to me.

Total value: $100

Diamond status

Worthless, I already have it and can book reservations for my partner when she’s traveling without me.

Total value: $0

Conclusion

The basic math here looks pretty good: I paid a $450 annual fee for what I have tried to conservatively calculate as $1,770 in value. Of course, part of that was a fluke: it would have been $250 less if American Express hadn’t awarded us two resort credits. Likewise, part of that was human error: it would have been $510 more if I had been able to trigger all 3 airline fee credits.

If you’re wondering whether the card is worth getting, the obvious answer is yes, if you can:

• get it at the end of the year;

• through a referral;

• with a plan to use your points for a high-value stay;

• and a plan to use your weekend night;

• and a plan to use your resort credit;

• and a plan to use your airline fee credit.

If you meet all those requirements, you can easily get several thousand dollars in value for a single $450 annual fee.

But this is the first card I had my partner sign up for in what Frequent Miler calls “two-player mode,” and let me tell you, it is absolutely exhausting. We ended up doing ok this time, but I’m not planning to try it again any time soon. You probably already know whether your partner has any interest in travel hacking, and if they don’t, you’re not going to convince them with some free cheese cubes in an Alaska Airlines lounge.

Reminder: restrictions do differ between different shopping portals

Starting online purchases at a shopping portal is one of the simplest techniques travel hackers use, and it’s also one of the most reminiscent of extreme couponing: click through an online portal (be sure to clear your browser’s cookies first), make a purchase, and you’ll earn some miles, points, or cashback from the portal in addition to your credit card rewards.

While there are dozens, if not hundreds, of different online shopping portals, with a little bit of experience they can come to seem more or less interchangeable (they’re mostly operated by the same firm on the backend), which can be both a good and bad thing. It’s a good thing when it means the same technique will work on multiple portals, like the Wall Street Journal/Barron’s subscription deal; it’s a bad thing when the same restrictions are imposed on each portal, or even across portals.

It’s worth keeping an eye out for differences between portal restrictions

For my sins, I’ve had to book a couple upcoming hotel stays with cash, and decided to see what the current situation was on my online shopping portal accounts. The problem, in general, is that merchants got wise to people double-dipping through both shopping portals and their proprietary rewards programs, and so began to limit portal payouts when you log into your rewards account before completing a reservation. To give a simple example, if you click through to Hotels.com through TopCashBack, you’ll receive 8% cashback if you make your reservation without logging in, but only 2% cashback if you log in first:

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BeFrugal is slightly more competitive, at 10% and 2.5%, respectively:

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While this may seem like a cheap move for Hotels.com (because it is), the logic is obvious: they already operate a loyalty program offering a rebate of “about” 10% on hotel stays (every ten nights booked through the site earns a free night of equal or lesser average value). Giving people an additional discount just for knowing about it must give their director of marketing enough heartburn as it is.

This compromise at least makes shoppers stop and think: it’s true 12.5% (through BeFrugal) is higher than 10%(logged into Hotels.com), but a 10% cash payout might be more valuable than a 10% in-kind payout with a 2.5% cash bonus. In fact, I think under virtually all circumstances it would be.

But not all shopping portals have identical restrictions

Ideally, what you’d like is a shopping portal with a competitive payout rate that still works on rewards-earning transactions, and that’s why it’s worth checking the restrictions on each portal, instead of just assuming they’re all identical.

Lemoney, for example, offers 5.5% cashback at Hotels.com without restriction on whether you’re also collecting Hotels.com free night credits:

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To be clear: while my full cashback amount has already tracked properly, it won’t be payable for months so there’s no way of telling whether I’ll actually receive the full amount.

I found the same was true at Hilton, where BeFrugal offers 6% cashback to non-members and non-elite members, but just 1.5% to Silver, Gold, and Diamond elites:

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While Lemoney offers 4% cashback to everyone:

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Conclusion

Shopping portals have never played a particularly large role in my travel hacking game, simply because I’ve always been fortunate enough to have access to adequate manufactured spend to meet my travel needs, so this isn’t meant to be a comprehensive look into shopping portals, let alone a recommendation to use one over another (although feel free to find my own personal referral links on my Support the Site! page).

But it is meant as a reminder that while shopping portal terms are often similar, they aren’t always identical, and the differences between them can end up being more lucrative than you expect, particularly when you do end up needing to pay cash for travel expenses.

Hyatt is burying Small Luxury Hotels, so keep an eye out for good values

Over at Running with Miles, Charlie Barkowski has been doing yeoman’s work tracking the “Small Luxury Hotels” eligible for Hyatt Category 1-4 free night certificates, meaning properties that cost up to 15,000 points per night. Check that out if you’re struggling to figure out where to redeem your Hyatt free night certificates.

Today, I want to make a few unrelated points about Small Luxury Hotels.

Non-Globalist World of Hyatt members should slightly prefer Small Luxury Hotels

All else being equal, World of Hyatt members, and Explorist and Discoverist elites, should prefer Small Luxury Hotels stays over otherwise-identical Hyatt properties. That’s because World of Hyatt reservations at Small Luxury Hotels come with continental breakfast for two, and at least the possibility of a 2 pm late checkout.

That shouldn’t be decisive for Globalist elites who receive breakfast and late checkout anyway, or if the Small Luxury Hotel property is more expensive, a worse value, or is much more inconvenient. But as a tiebreaker for the casual Hyatt traveler, it’s worth keeping in mind.

Hyatt buries Small Luxury Hotels at the end of search results, but it’s worth digging

If you search for Hyatt stays in New York City, you’ll see an ocean of properties stretching from the Grand Hyatt on East 42nd Street to the Hyatt Place in Princeton, New Jersey, before you’ll see the HGU NEW YORK, at 34 East 32nd Street.

That’s because all Small Luxury Hotels results are buried at the very end of the search results, long after most people stop looking. Slightly better is the map view, which shows all the properties in a given city, but which makes it more difficult to compare their relative value.

In destinations without Hyatt properties, Small Luxury Hotels are a potential game-changer

Since Manhattan offers a range of Hyatt properties, Small Luxury Hotels aren’t likely to play a huge role in a travel hacking strategy there. But in other areas, they’re potentially decisive. Consider a stay in the center of London next month. There are only two Hyatt properties, the Hyatt Regency London - The Churchill and the Andaz London Liverpool Street, both at 25,000 World of Hyatt points.

But there are 6 Small Luxury Hotels properties, ranging between 20,000 and 25,000 points, in or near the center of London. On a smattering of sample dates, I saw redemption rates at those properties between 1.58 and 2.84 cents per World of Hyatt point. Not breathtaking, but properly calibrated to the value of the program as a whole.

Compare that to Hilton’s central London properties on the same dates. From a high of 0.61 cents per point at the DoubleTree by Hilton Hotel London - Kensington (50,000 points for a 231 GBP stay) to a low of 0.45 cents per point at the London Hilton on Park Lane (80,000 points for a 273 GBP stay), what you see across the board from Hilton is replacement-level redemptions. There’s nothing wrong with those redemptions — I would make them myself in a pinch, and a 5th-night-free redemption would improve the value further — but the Small Luxury Hotel redemptions offer the kind of outsized value we’ve come to expect from Hyatt points.

Conclusion

The addition of Small Luxury Hotels as a redemption option in World of Hyatt hasn’t increased the value of individual Hyatt points (still worth between 1.5 and 3 cents each), nor has it increased the value of individual Hilton points (still worth about 0.5 cents each).

What it has done is increase the value of a portfolio of both Hyatt and Hilton points, allowing Hyatt points to be redeemed more readily in cities like London and New York where Hilton points are typically redeemed at their replacement value, while allowing Hilton points to be saved up for redemption at the very few properties and redemptions where they get outsized value.

Four use cases for Hilton credit card spend

Lately I’ve been mulling a series of posts by Nick Reyes over at Frequent Miler about the relative value of earning Hilton Honors points directly through credit card spend, versus purchasing them for 0.5 cents each during Hilton’s periodic point sales. As someone who considers Hilton indispensable to my travel hacking practice, I took the opportunity to reflect on what I might be doing wrong (or right).

The Deal

As Reyes explains, the opportunity comes from the fact that while Hilton normally sells their points for 1 cent each, they very frequently offer sales where you can purchase up to 80,000 points per calendar year for $800, and receive 80,000 bonus points, bringing the cost per point down to 0.5 cents.

Moreover, you should be able to receive the same deal clicking through the TopCashBack portal and earning 2.5% cash back, or up to $20 on an $800 purchase. And of course the purchase itself will earn cash back, worth another $16 on a 2% cash back credit card. That means you can purchase up to 160,000 Hilton Honors points per year for $764, or 0.4775 cents each.

If that’s the cash cost of 160,000 Hilton Honors points, you should be at least reluctant, if not unwilling, to pay more than that in opportunity cost. For example, Hilton Honors credit cards earn 3 points per dollar on unbonused spend. If you can otherwise earn 2% cash back on unbonused spend, putting the same spend on a HIlton credit card would mean paying 0.67 cents per points — 40% more than they cost on the open market.

Even manufacturing spend in the Hilton Ascend bonus categories may mean overpaying: earning 6 Hilton Honors points per dollar spent at grocery stores means giving up 3 cents in travel on the US Bank Flexperks Travel Rewards card, while at gas stations it means giving up 2 Ultimate Rewards points per dollar on the Chase Ink Plus and Ink Cash.

All that is straightforward enough. What I wondered was, under what circumstances does it still make sense to put spend on a Hilton co-branded credit card?

Reimbursed business travel

It’s easy to forget today, but travel loyalty programs were not actually designed with cheapskates like me in mind. Instead, they were meant to encourage business travelers with control over their reservations to prefer one travel provider over another by offering to kick back a portion of the company’s travel budget to the traveler for later, personal use. And to an extent, that’s still what they do.

If you’re a reimbursed business traveler, it can make sense to charge your Hilton reservations to an Ascend or Aspire credit card. The former earns 12 points, and the latter 14 points, per dollar spent at Hilton properties, including taxes, resort fees, and room charges, the equivalent of 5.73% and 6.69% cash back, respectively (since 12 points can be bought for 5.73 cents during 100% bonus promotions on purchased points). That compares favorably to the 3 ThankYou points per dollar spent at hotels with the Citi ThankYou Prestige and 2 Ultimate Rewards points per dollar spent with the Chase Ink Plus.

Indeed, you would need to value the marginal ThankYou point at 1.91 or 2.23 cents each, and the marginal Ultimate Rewards point at 2.865 or 3.34 cents each to be willing to give up 12 or 14 Hilton Honors points per dollar spent. Those are not incredibly unrealistic values, but they’re well above the rate at which I would acquire those points speculatively.

And of course, American Express Offers linked to your Hilton credit cards may offer substantial additional savings, like the $70 off $350 offer I took advantage of in Hawaii last month.

Ascend free weekend night award spend threshold

If you don’t manufacture spend, and you don’t have reimbursed travel you can direct to Hilton, then you probably shouldn’t carry an Aspire card (with its $450 annual fee) and you absolutely should not carry an Ascend card unless you’re willing to meet the $15,000 cardmember year spend threshold to trigger a free weekend night award.

That free weekend night award has two costs: the card’s $95 annual fee, and the opportunity cost of putting $15,000 on the Ascend card instead of your next best alternative. Here I’ll assume that opportunity cost is 2% for unbonused spend, and 3% for bonused spend (gas stations and grocery stores). You should re-run these calculations if your opportunity cost differs, of course.

That brings the total cost of the free weekend night award to $395 or $545, from which we can back out the 45,000 points (worth $214.88) or 90,000 (worth $429.75) points earned on the spend, for a net cost of $180.12 or $115.25.

Using the same base cost of 0.4775 cents per Hilton point, we know $180.12 can buy you 37,721 points, and $115.25 can buy you 24,136 points. In other words, any Hilton free weekend night redemption above those values leaves you at least marginally better off than if you had put the $15,000 in spend on a 2% or 3% cash back card instead and simply purchased the corresponding number of points.

But ideally, you won’t be making breakeven redemptions. At a 95,000-point property, a free weekend night is worth $453.63 in purchased points, for a profit of $273.51 or $338.38. If the new Waldorf Astoria Maldives Ithaafushi really charges 120,000 points per night for a standard award — and those awards can be booked with free weekend night awards — then the potential profit is even larger.

Increased float

Even replacement-level affiliate bloggers have enough of a conscience to warn the folks they sell credit cards to that you should pay off your balance in full every month, since the high interest rates credit cards charge (sometimes after a low-interest or zero-interest introductory period) will almost immediately reclaim the value of any rewards you earn on spend.

A newbie taking this advice literally might use their manufactured spend to immediately pay off the card used to generate it. And indeed, during opportunities like the unlimited 5% cash back offered by Wells Fargo credit cards in the past, that’s sometimes the most lucrative strategy.

But more experienced folks understand that while credit card interest should be avoided, there are lots of advantages to holding onto cash, rather than plowing it back into the card used to generate it. A card with a 30-day billing cycle and 20-day grace period effectively offers a series of rolling 50-day interest-free loans. The more lucrative your short-term investment opportunities, the more willing you should be to maximize the value of those interest-free loans, a strategy discussed by Sam Simon and Robert Dwyer in the February 1, 2019, episode of their Milenomics Squared podcast.

That means if your credit limits are too low to meet your needs for cash to plow into your most profitable gigs, you may well find it worthwhile to put spend on a second-best or third-best card.

Ascend Hilton Honors Diamond spend threshold

In general, Hilton Honor Diamond status doesn’t afford very many concrete or guaranteed benefits. In fact, the only guaranteed benefit I’m aware of is that Gold members are only entitled to executive club access when they’re upgraded to a club floor, while Diamond members receive club access even when they are not upgraded. That’s not nothing, but it’s also not much.

Moreover, Hilton status seems to last more or less forever. So while Diamond status is a benefit of spending $40,000 per year on the Hilton Honors Ascend American Express card, you don’t have to spend $40,000 every year. If you spend that much even once, you’ll probably have Diamond status for at least 2-3 years, if not longer.

However, if you’re keeping the Ascend in order to hit the $15,000 spend threshold every cardmember year, you may find it worthwhile to also hit the $40,000 Diamond status spend threshold every few years, especially if you can do so in bonused spend categories.

Bonus use case: you just need more points

As Reyes pointed out in his post, while each individual Hilton account holder is limited to purchasing 80,000 (and receiving 160,000) points per year, Hilton has made it easy to transfer and pool points, so in principle you can simply enlist as many people as needed to buy points during each promotion and then combine them for your desired redemptions.

In reality, conscripting friends and family to help you spend thousands of dollars on virtual currency is as likely to generate dead-eyed stares as it is Hilton Honors points. Once you’ve picked the low-hanging fruit of yourself, your spouse, and your kids, you might simply not have any good options for additional points purchases. At that point, instead of wasting time trying to cajole your relatives into playing along, you might find that it’s worth slightly “over-paying” to avoid the fuss.

Top-tier Hilton properties eligible for the Aspire resort credit

Thanks to lifecycle effects I haven’t taken as many sprawling international vacations as I did when my life was governed by the academic calendar, which has had the ancillary effect of nudging me towards somewhat more luxurious travel plans. To give a trivial illustration, 250,000 annual Ultimate Rewards points earned through office supply spend on a Chase Ink Plus are worth 16 nights at 15,000-point World of Hyatt properties but only 8 nights at 30,000-point World of Hyatt properties, so the decision of whether to stay at a 15,000-point property or a 30,000-point property is in part governed by how many nights I need to book each year.

That has made me more curious about top-tier properties in each chain, like the Grand Wailea in Maui where we stayed earlier this month. Since I earn a lot of Hilton Honors points (and they can be purchased for less than 0.5 cents each through a cash back portal during Hilton’s frequent promotions), I wanted to take a look at all the top-tier Hilton properties where the Hilton Honors Aspire American Express card’s $250 resort credit can be redeemed.

In principle, these would be the properties where you can get the most value (in points) from American Express free weekend night certificates, the elite 5th-night-free benefit on award stays, and the Aspire credit card resort statement credit. I couldn’t find an existing list anywhere online, so I decided to assemble it myself for my and your future reference.

95,000-point Hilton Honors properties eligible for $250 Aspire resort credit

Note that due to Hilton variable award pricing, these are properties where the maximum, standard room award rate is 95,000 points. The actual rate for the dates you want may vary, sometimes substantially, below the maximum rate. After each property, I’ve indicated a sample redemption value for a 5-night, 380,000-point reservation 6 months from now.

Waldorf Astoria

• Grand Wailea, A Waldorf Astoria Resort, $3,467.42 (0.96 cents per point)

Curio Collection by Hilton

• Hotel del Coronado, Curio Collection by Hilton, $2,342.41 (0.62 cents per point)

Conrad

• Conrad Fort Lauderdale Beach, $1,903.73 (0.5 cents per point)

• Conrad Maldives Rangali Island, $4,249.29 (1.12 cents per point)

• Conrad Koh Samui, $3,404.35 (0.9 cents per point)

Hilton

• Hilton Odawara Resort & Spa, $1,967.32 (0.52 cents per point)

• Hilton Seychelles Northolme Resort & Spa, $3,111.88 (0.82 cents per point)

A clarifying exercise

I arrived at this list by applying two filters to the entire list of Hilton properties: eliminate properties that don’t have a maximum redemption rate of 95,000 points per night, and eliminate properties that don’t qualify for the Aspire resort credit. However, while this is a good way of determining the properties where you can take advantage of Hilton program rules to save the most points, it says nothing about where you can use Hilton Honors to save the most money. Indeed, since I looked at 5-night stays 6 months in the future (July, 2019), I didn’t even look at the highest-dollar-value redemptions at these properties, most of which I assume would fall over spring break, Thanksgiving, Christmas, or other peak-travel holidays.

Moreover, while there are only 15 total properties in the Hilton Honors system that charge a maximum of 95,000 points per night (according to Loyalty Lobby’s March, 2018, update) there are 65 properties that charge 80,000 points per night and 145 that charge a maximum of 70,000 points per night. In other words, there are ample areas to fish for high-value redemptions outside the 95,000-point pond.

Conclusion

I am a big fan of Hilton Honors, but since I use my miles and points to book the trips I want to go on, I was a bit disappointed by my findings. I had a great time at the Grand Wailea, and would happily return there, but don’t have any special interest in visiting the Maldives, Seychelles, or Koh Samui, let alone Coronado, California, or Fort Lauderdale, Florida, so the Hilton Odawara is the only property on this list I could conceivably plan on visiting in the foreseeable future.

Compare that to the list of top-tier World of Hyatt properties: New York, Paris, Milan, Zurich, Sydney, and Tokyo are all cities I’d be happy to splurge for a stay on with points (New York’s Park Hyatt was a bust, but Zurich’s was lovely).

That doesn’t mean you can’t get good value during your first year of Aspire cardmembership stacking free-weekend-night and 5th-night-free awards with the card’s $250 resort credit. But it does mean that you may want to hunt for the highest dollar-value savings outside the highest point-cost properties.

Even more Hilton Honors IT nonsense

Back in September, 2018, Robert Dwyer wrote at Milenomics about all the real and potential problems you might encounter redeeming Hilton Honors free weekend night certificates. Having re-read that post, I thought I was locked, loaded, and ready to redeem my own Hilton Honors Ascend free weekend night certificate for an upcoming trip to New York City.

It didn’t work out that way.

Good news: free weekend night awards may have gotten easier to book

Going into this call, my assumption was that I’d run into one of the same obstacles Robert did: I didn’t have enough points in my account to book a night entirely with points, even though I didn’t intend to use any points at all.

That did not end up being my problem. After I identified myself, the phone rep was able to find and apply my free weekend night certificate and complete the reservation without any problem, even though I had less than 6,000 Hilton Honors points in my account, so they seem to have fixed Robert’s ninth obstacle.

Interestingly, the phone rep was willing to let me use my free weekend night award to book any standard room award. Now that Hilton has started charging different prices for different “standard” rooms on the same night this is potentially a big advantage, for a couple of reasons.

First, for reservations booked entirely with free weekend night certificates, it may increase the value of the certificate by letting you book a larger room or one with more beds for a single “price.”

But second, depending on the property, it may also increase the value of your points when combining a points reservations with a free weekend night award reservation. That’s for the simple reason that under many circumstances a hotel may prefer to let you stay in a “better” room for multiple nights rather than force you to move every day and their housekeeping staff to turn over multiple rooms multiple times.

Your experience will vary, but using a free weekend night award for the first night of a stay may be one strategy for working your way into a larger or better room for the entire length of your stay.

Bad news: points are not available instantly after awards are cancelled

This is not exactly a new problem, so much as one Hilton has never really figured out how they want to handle. When I wrote about the issue in 2017, I advised cancelling, instead of changing, award redemptions since changing reservations did not redeposit the price difference in your account.

But now the problem has gotten worse, with award cancellations not immediately redepositing points either. I ran into this exact problem yesterday trying to rebook a 3-night award stay as a 2-night award stay (with the first night replaced with my weekend night award). I waited patiently for the points to be redeposited so I could rebook the last two nights, but they never were (and still haven’t been).

My pet theory having only looked into it over the course of a frustrating evening is that these developments are connected. When I opened my free weekend night award reservation, I saw that instead of simply saying a certificate or award had been used, instead my reservation stated that 67,000 points had been redeemed. If free weekend awards are being converted into points before being applied to reservations, that would mean you could theoretically book any standard night at any of the most expensive Hilton properties, cancel the reservation, and receive 95,000 points redeposited in your account.

If they really implemented free weekend night awards in such a crude way, adding a level of scrutiny to those free weekend night reservations necessarily means applying the same scrutiny to all cancelled award reservations. That is an issue that’s trivial to work around, but only if you know it exists.

And now you know.

The Hilton Honors Ascend American Express Priority Pass Membership "Year"

Unlimited access to the Priority Pass network of airport lounges, which was long an afterthought compared to airline lounges and, more recently, the superb American Express Centurion lounges, has quietly become an impressive benefit of many super-premium credit cards, like American Express Platinum cards, the Chase Sapphire Reserve, and the Citi Prestige. In part that’s because Priority Pass has aggressively added airport restaurant locations where you can typically receive about $28 towards your food and drink bill (excluding gratuities). When I first started tracking that option, I recorded just 23 participating restaurants. The number is now up to 49!

Credit cards issued in the United States have typically offered either unlimited Priority Pass memberships or, like the Chase Ink Plus, “memberships” in name only where “members” pay $32 or so for lounge access. Obviously those memberships don’t offer any value at all at non-lounge locations, since the benefit is usually capped at $28-$30, although they might theoretically still be useful on long international layovers.

The Hilton Honors Ascend American Express struck an interesting compromise, offering a Priority Pass membership that includes 10 free visits per year, a benefit I enjoyed last year (although my partner’s new Hilton Honors Aspire card will give us both unlimited free visits while traveling together).

If you have an Ascend card and don’t otherwise have unlimited Priority Pass access, you should already be asking an important question: what’s a “year?”

Three ways a year could be defined

The two most common ways credit card benefits are restricted are by cardmember year and by calendar year. For example, American Express airline fee reimbursements are offered on a calendar year basis, while American Express Delta companion tickets are offered on a cardmember year basis, with the companion ticket appearing in your SkyMiles account shortly after your annual fee is charged each cardmember year.

There’s a third option, however, when benefits are provided by a third party: third-party program year benefits. For example, American Express Platinum cards offer Hilton Honors Gold status as an incidental benefit, but your Hilton Honors Gold status doesn’t depend on either the calendar year or your cardmember anniversary. Instead, it depends on the Hilton Honors program year, and your Gold status will continue for a year or longer even if you don’t renew your Platinum card.

American Express claims Priority Pass membership is based on a third-party program year

You can find American Express’s description of the Ascend Priority Pass benefit on the online application or by logging into your account. It’s more or less identical in both cases, and crystal clear (this text comes from the description in my online account, emphasis mine throughout):

“Your Priority Pass Membership year begins on the date you enroll. Once enrolled, you will receive your Priority Pass Select card directly from Priority Pass within 10-14 business days. There is no membership fee with your Hilton Honors American Express Ascend Card. With your Hilton Honors American Express Ascend Card you will receive 10 complimentary lounge visits each Priority Pass Membership year. Once your 10 complimentary lounge visits are used, all subsequent lounge visits during the remainder of the Priority Pass Membership year are subject to a fee equal to the amount of the guest visit fee of the Priority Pass Standard program per person per visit, which will be automatically charged to your Card. To check on your remaining complimentary visit balance, please contact Priority Pass directly. Any unused complimentary lounge visits will be forfeited at the end of each Priority Pass Membership year.”

In other words, whenever you get around to enrolling in Priority Pass, the clock starts on your Priority Pass membership year, during which you can make 10 total visits, including guests. This would theoretically be gameable, for example by waiting until a few weeks before the first trip you expect to use Priority Pass on, thereby delaying the start of your Priority Pass membership year.

But it’s not true.

The Hilton Honors Ascend Priority Pass membership is a calendar year benefit

I know travel hackers all fancy themselves jailhouse lawyers, so before anyone starts commenting about how crystal clear the terms and conditions are, let me say: I know how crystal clear the terms and conditions are. But if you rely on the terms and conditions, you’re going to end up with a bunch of $32 credit card charges before you know it.

Fortunately, I only ended up with one, but it illustrates the issue perfectly:

• My Hilton Honors Ascend annual fee was charged on January 19, 2018;

• I registered for Priority Pass on February 7, 2018;

• I made 11 visits between August 20, 2018, and December 26, 2018, and was charged $32 for the 11th visit;

• I made another visit on January 2, 2019, and was not charged.

There’s simply no other way to explain this set of facts than the benefit being based on the calendar year, contrary to the explicit terms and conditions of the benefit.

My secondary piece of evidence is that I called Priority Pass today to ask how the benefit works, and spoke to a lovely woman with a perfect British accent who nevertheless understood no English. After both of us shouted at each other in perfect English long enough, she finally understood my question and told me I get 10 free visits per calendar year, I’ve used 1, and I have 9 remaining. At that point I politely thanked her and she politely hung up on me, to both of our relief.

Conclusion

For me, travel hacking is about staying focused on a simple question: how does it really work? The systems we take advantage of lie on the intersection of marketing, engineering, and law. Sometimes the marketers talk to the engineers, sometimes the engineers talk to the lawyers, and sometimes nobody talks to anybody at all. It isn’t enough to ask what the marketers intended, or what the lawyers wrote, if you don’t pay attention to what the engineers actually programmed.

How bad would a Hyatt devaluation need to be?

I’ve been following with interest the changes Hyatt has made to certain types of award reservations. To roughly summarize the changes:

• points can now be redeemed for “premium” suite award nights;

• Points + Cash can now be redeemed for standard and premium suites;

• qualifying paid stays can now be upgraded to premium suites with points;

• the cash co-pay on Points + Cash stays is now 50% of the “standard” room rate for the room type you’re booking instead of a fixed amount based on hotel category;

• a new 40,000-point redemption tier will be introduced to cover certain newly-acquired luxury properties.

I’m frankly not sure if it was part of this update or not, but I also noticed recently that award nights at Hyatt Ziva and Zilara all-inclusive properties can now be booked online (you used to have to call to book).

Hyatt is a competitive program for travel hackers

If you earn miles and points mostly or exclusively through manufactured spend this shouldn’t come as surprise, but to break it down simply:

• a Category 1 Hyatt property costs 5,000 points per night, or $3,333 in spend on a Chase Freedom Unlimited or $1,000 on a Chase Ink Cash or Ink Plus at office supply stores;

• a Category 4 Hyatt property costs 15,000 points per night, or $10,000 in spend on a Freedom Unlimited or $3,000 in spend on Ink Cash or Plus;

• a top-tier Category 7 property costs 30,000 points per night, or $20,000 on Freedom Unlimited or $6,000 on Ink Cash or Plus.

We can break down Hilton’s award chart in the same way:

• a bottom-tier Hilton property costs 5,000 points per night, or $833 in grocery store or gas station spend on an American Express Ascend card;

• a mid-tier Hilton property costs 50,000 points per night, or $8,333 in bonused spend;

• and a top-tier Hilton property costs 95,000 points, or $15,833 in bonused spend.

(Note that since grocery store spend costs about 50% more than in-person unbonused spend, the out-of-pocket costs for the same spot on the Hilton award chart end up being somewhat more expensive than Hyatt).

This is what I mean by a “competitive” program: Hyatt properties won’t always be cheaper than Hilton properties in a specific city or on particular dates, but having access to both programs gives you a better chance of paying as little as possible for the trips you want to take than relying solely on one program or the other and being stuck paying cash when it fails you.

Likewise, having credit cards that are useful for unbonused spend, office supply store spend, and grocery store spend means you’re able to take advantage of more promotions and opportunities, instead of relying on a single merchant or bonus category.

That brings me to today’s topic.

How bad would a Hyatt devaluation need to be to make the program uncompetitive?

I think it’s useful to think through questions like this ahead of time, so you don’t fall into the trap of motivated reasoning once a devaluation actually happens (something credit card affiliate bloggers are especially vulnerable to, but a risk for anyone).

You can imagine multiple forms a Hyatt devaluation might take:

• Hyatt could change or end their transfer relationship with Chase. This is the least likely situation in the short term since Chase loudly promotes its uniform transfer ratio, but there’s no natural law that says Hyatt will remain a Chase partner forever, or that Chase will never revamp the Ultimate Rewards program.

• Hyatt could introduce higher award categories and steadily shift properties upwards. Hyatt told Pizza in Motion that they have “no plans for any Hyatt-branded hotels or resorts to move to a new Category 8,” but all that wording requires is that the Park Hyatt sign come down and be replaced with a Small Luxury Hotels of the World or Joie de Vivre sign. No Hyatt branding? No problem.

• Hyatt could restrict award space or introduce dynamic pricing. This is in many ways the most likely or even inevitable form a devaluation will take, since Hilton has had dynamic pricing for years and Marriott will launch it in 2019. 30,000-point properties might limit their availability to a few low-season weeks per year, while mid-tier properties might cost a few thousand points less for part of the year and tens of thousands of points more when people actually want to visit.

A change to the relationship with Chase would be the most catastrophic from a travel hacker’s point of view. Changing the transfer ratio or perhaps capping annual points transfers would make Hyatt a truly niche program, still worthwhile under specific conditions but uncompetitive with Hilton or even Radisson Rewards, which has US Bank co-branded credit cards that still earn 5 points per dollar on unbonused spend and a much larger footprint than Hyatt.

Meanwhile, category inflation isn’t the end of the world as long as the Chase relationship remains the same, although eventually you might see your favorite properties inflated out of eligibility for annual credit card free night certificates (currently good at Category 1-4 properties).

Conclusion

There should be no question in your mind that something will eventually give in the World of Hyatt program, and this post isn’t about predicting whether or not it will happen — it definitely will. There has to be enough money to go around between Chase, Hyatt, and Hyatt’s owner-operators, and a fixed credit card earning ratio and fixed award chart are simply incompatible with that. I don’t know which piece will buckle first under the pressure, but the transmission mechanism between Chase Ultimate Rewards, World of Hyatt, and award availability and price will change because it has to change.

The point of this post is to encourage you to think in advance about what kinds of changes would make you walk away from the program, or at least radically reduce your dependence on it. How bad would the transfer ratio have to become? How hard would it have to be to find award availability? How low would your typical redemption value have to fall?

If you don’t think about it in advance, then when the devaluations do start to roll in and you’re bombarded with affiliate bloggers explaining how “it’s not really that bad,” you’re not going to be ready to tell if they’re right or not.

Gaming out my Waldorf Astoria stay

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.

Free Hilton Honors transfers and my 2.2 cent per point redemption

As we near the winter holiday season, I’ve started planning a New Year jaunt to celebrate my recent nuptials. We already planned to visit the West Coast after Christmas, and since there was an expiring Alaska Airlines Companion Ticket in the mix, I decided to see if I could use the West Coast as a stopover to one of Alaska’s more far-flung destinations. Alaska offers nonstop flights from Portland to several Hawaiian islands, so I checked award availability at one of Hilton’s top-tier, 95,000-point properties: the “Grand Wailea, A Waldorf Astoria Resort.”

Transferring Hilton Honors points is now free and fast (but not instant)

I was surprised to see that for 5 nights right after the New Year, the Grand Wailea had wide open award availability for their standard “Terrace View” room. There was no way I was going to book anything less than a 5-night stay at a 95,000-point property, thanks to Hilton’s fifth-night-free policy on award stays for elite members. But a 5-night stay would still cost 380,000 Hilton Honors points, more than I happened to have in my account. Even after cancelling a couple Hilton reservations and rebooking those stays at Hyatt properties, I was about 100,000 points short.

That’s when I remembered that as part of the April 2, 2018, revamp of the Hilton Honors program, “points pooling” and “points transfers” are now free between all members. Let me start by saying it’s not immediately clear to me exactly why Hilton distinguishes “pooling” from “transfer” transactions: in both cases only the recipient of the transfer, or the creator of the pool, is able to redeem the points, and in both cases the contributor of the points is able to select the number of points they want the recipient to be able to redeem.

The limits on transfers and pooling are somewhat complex, so let me start by sharing the terms and conditions as they’re presented on the Hilton website:

“Hilton Honors Members can transfer Hilton Honors Points to another Hilton Honors Member through Points Pooling or 1-to-1 transfer in increments of 1,000 Points and up to 500,000 Points. Each Hilton Honors Member is limited to sending no more than five hundred thousand (500,000) Points and receiving two million (2,000,000) Points via Points Pooling or Transfers combined per calendar year. Each Hilton Honors Member is limited to making six (6) transfers to other member accounts and six (6) Hilton Points Pooling transactions per calendar year. Invitations to join a Points Pool is not considered transactional. Transactions refer to the transfer of Points to another member account either through 1-to-1 account transfers or through Points Pooling.”

There are three moving pieces here:

• The total number of points you can send in either transfer or pooling transactions per calendar year (500,000);

• The total number of points you can receive in either transfer or pooling transactions per calendar year (2,000,000);

• The total number of outbound transfer and outbound pooling transactions you can make per calendar year (6 transfer and 6 pooling transactions).

That’s my plain English reading of the terms and conditions, but if anyone has run up against these limits in practice or found a way around them, let me and your fellow readers know in the comments.

All that being said, yesterday I asked a travel hacking buddy to transfer over the points I needed to book my 5-night stay at the Grand Wailea. Then I waited. And waited. And waited.

Ok, I only waited about 11 hours, but the point is, don’t expect points transfers to take place immediately, and don’t count on them if you need points for an immediate redemption.

I received a confirmation e-mail (as did the person sending the points) a few minutes after noon the day after the request, so it’s possible they run a batch process every day at noon to execute the previous day’s transfers.

I redeemed 380,000 points for a $8,466 stay

The stay I redeemed 380,000 points for would otherwise cost:

• $7,199 room rate;

• $200 resort fee;

• and $1,067 taxes.

That gives an almost comical 2.2 cent per Hilton Honors point redemption, or 13.2% in value on my grocery store manufactured spend, where I earn 6 Hilton Honors points per dollar on my American Express Ascend card.

You may remember that as part of the April revamp of the program, Hilton no longer excludes Waldorf Astoria resorts from the Gold and Diamond elite breakfast benefit. After reaching out to the property for an explanation of their benefit, the “Room Reservations Agent” explained that:

“You would receive a daily $15.00 per day up to 2 person a in room dining credit. Unfortunately the $15.00 in Only for in Room dining" [sic].

Being a pedant, I looked up the Grand Wailea’s in-room dining menu, and there actually are several items at or below the $15 price point. I hope you like avocado toast as much as I do!

Did I overpay?

To be clear, I booked this particular top-tier property mainly for the blog content, since I couldn’t find any useful information online about how Diamond benefits there work in practice.

But, being me, I also did a quick rundown of alternate properties, in case you want to go to Maui for some reason besides getting a couple good blog posts out of it. Here are the properties that still have award availability as of today:

• Wailea Beach Resort - Marriott, Maui. 200,000 Marriott Rewards points for a 5-night stay.

• Days Inn by Wyndham Maui Oceanfront. 75,000 Wyndham Rewards points for a 5-night stay.

Of course, money can also be exchanged for goods and services, and some light browsing turned up what seems like a pretty good deal through Agoda.com, for a total of $2936.03 for five nights at the Hyatt Regency Maui Resort and Spa, a rate that even includes breakfast.

Using 200,000 Marriott Rewards points (worth $2,000 in cash if transferred from Ultimate Rewards) and $2,936 as my most likely alternatives, I redeemed 380,000 Hilton Honors points at between 0.5 and 0.77 cents each, a solid but unremarkable redemption.

Obviously that’s not going to stop me from bragging to friends and family about my $8,500 honeymoon.

Conclusion

I’m very curious how this trip will work out, since after reading a slew of reviews online it seems like the Grand Wailea changes their policies every few weeks. My conservative hope is an upgrade from our standard “terrace view” room to at least an ocean view room, since that was one of the delights of our stay at the Hyatt Zilara Rose Hall. The property also has what looks like an all-suites tower, which Hilton Diamonds seem to very occasionally be upgraded to for free (paid upgrades are also available).

We plan to rent a car in order to see some other parts of the island, which means at a bare minimum paying $30 per day for valet parking, since the hotel doesn’t have a self-park option. Given the certainty of those expenses, plus any food and drinks we charge to our room, I’m thinking hard about whether to sign up for an Aspire card before we make the trip. I have the option of upgrading my Ascend card, which would sacrifice my bonused grocery store earning rate, so that’s of marginal interest. But my partner has never had a Hilton credit card and she’d be eligible for the current 150,000-point signup bonus, plus a $250 resort credit during our stay.