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

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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

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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

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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

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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"

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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.

East Coast Alaska Airlines companion fare strategies

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As I mentioned last week, In order to get to Maui and back I stitched together 3 legs using a single Alaska Airlines companion ticket. While folks on the West Coast are probably familiar with Alaska and their companion ticket, now that the merger with Virgin America is complete it might be time for residents of some East Coast cities who had ruled out Alaska because of its limited route network to take another look.

Two flavors of Alaska Airlines companion fares

There are technically two flavors of Alaska Airlines companion fares. For the past several years Bank of America has offered a taxes-and-fees-only companion fare to new Alaska Airlines Visa cardmembers after spending $1,000 on the card within 90 days.

Then, on each account anniversary, you’ll receive another companion fare for $99 plus taxes and fees.

Besides the $99 co-pay for anniversary companion fares the two are otherwise identical.

What’s so great about Alaska Airlines companion fares?

Three features make Alaska companion fares unique:

  1. they can be used systemwide;

  2. they can be used on any economy fare;

  3. and both passengers receive mileage credit as if they were both flying on paid tickets.

In fact, the only restriction I’ve ever encountered using a companion fare is that the Bank of America cardholder has to be either one of the two passengers traveling on the fare or have their name on the credit card used to make the reservation.

The fare does not have to be paid for with the Bank of America credit card that triggered the fare. You can even use an authorized user card, as long as it has the name of the Bank of America cardholder, and even that isn’t required if the Bank of America cardholder is one of the passengers.

That means using an Alaska companion fare isn’t mutually exclusive with many methods of payment, for example using a Chase Sapphire or Barclaycard Arrival Plus card for trip delay insurance, or a US Bank Flexperks Travel Rewards card for a Real-Time Rewards redemption.

A final note on fares: since the companion fare can be used to book any economy fare class, and both tickets book into the same fare class, you can use the companion fare to book tickets that are upgradeable using miles or MVP Gold guest upgrades. However, that upgrade space is extremely limited so I would not suggest paying more for an upgradeable fare speculatively if upgrade space is not available at the time of your booking; it likely never will be.

Alaska Airlines routes from the East Coast

Alaska serves a surprisingly large number of cities, especially now that Virgin America’s routes have been integrated into the system, but they are almost entirely reliant on five West Coast hubs: Seattle, Portland, Los Angeles, San Francisco, and San Diego.

That means flying from the East Coast to anywhere in the middle of the country will require backtracking: flying first to the West Coast, then connecting to a flight retracing your steps. You probably won’t want to do that — Seattle is a long way out of the way if you want to fly between Washington, DC, and Cancun.

However, lots of people fly to the West Coast as their final destination, and others fly onward to points West, North, or South, and for those folks the companion fare can still provide a fantastic value.

What I’ve done is break up Alaska Eastern time zone airports into six buckets, based on which of Alaska’s hubs are served from that airport.

Seattle

  • Tampa (TPA)

  • Atlanta (ATL)

  • Charleston (CHS)

  • Indianapolis (IND)

  • Columbus (CMH)

  • Detroit (DTW)

  • Pittsburgh (PIT)

Seattle and San Francisco

  • Raleigh/Durham (RDU)

Seattle, San Francisco, and Los Angeles

  • Fort Lauderdale (FLL)

  • Washington (IAD)

Seattle, Portland, San Francisco, and Los Angeles

  • Washington (DCA)

  • Philadelphia (PHL)

  • New York City (JFK) (plus San Jose and Las Vegas)

Seattle, Portland, San Francisco, and San Diego

  • Orlando (ORL)

Seattle, Portland, San Francisco, Los Angeles, and San Diego

  • Baltimore (BWI)

  • Newark (EWR) (plus San Jose)

  • Boston (BOS)

Three strategies for East Coast companion fares

If you live in or near one of those Eastern cities, I think there are at least three useful ways to judge the value of Alaska Airlines companion fares: connecting onward, backtracking, and non-stops.

Connecting onward is the most obviously high-value use: if you fly to Hawaii or the Pacific coast of Mexico at least once per year, and are willing to do so in economy, the ability to book any economy fare in the system can give you enormous value and flexibility. For example, from Washington, DC, there are no non-stop flights to Hawaii, so you’ll have to make a connection somewhere. If that’s the case, why not Seattle instead of Atlanta? Over the Thanksgiving dates I checked from DC, Alaska flights to Hawaii were already the cheapest options — adding a companion fare is icing on the cake. From New York, Alaska was the cheapest option to every Hawaiian island but Kauai (Delta undercut them by $15).

Backtracking is a less obviously appealing option, as I gestured at above. However, for many destinations in the Mountain West, it can still make sense. For example, my hometown of Missoula, MT, is a notoriously expensive city to fly in and out of (fortunately flights are also very often overbooked, and I received my only $1200 voluntary denied boarding voucher there). Over the Thanksgiving weekend, for example, Delta isn’t selling fares eligible for American Express companion tickets, so two tickets would cost $1,596, while two Alaska tickets would cost just $1,373 with a companion fare. A $223 savings isn’t revolutionary, but it’s still more than the Alaska Airlines Visa’s $75 annual fee.

Finally, obviously a lot of people have perfectly good reasons to fly between the East and West coasts without connecting at all. If you live in Baltimore, New York, or Boston, you might simply use Alaska companion fares to pay for the occasional trip to the West Coast. It’s lovely there!

The point is, the Alaska companion fare is such a good deal it’s worth considering even if you don’t think of yourself as a “typical” Alaska passenger, which is to say someone who commutes up and down the West Coast.

Alaska Companion Fare routing rules

Here I’m leaning entirely on Scott Mackenzie at Travel Codex, who is the authority on all things Alaska Airlines:

“Although the terms and conditions say the fare must be for round-trip travel, this isn’t strictly true. You can book one-way travel. You can book open jaws. You can book multi-city travel between completely different cities. I’ve confirmed that Austin to Seattle, Portland to Maui, and Honolulu to Sacramento — all on different dates — will qualify…

What you can’t do is book travel that is clearly not anything close to round-trip. In the example of AUS-SEA//PDX-OGG//HNL-SMF we flew west and then flew east. Kinda sorta maybe round-trip, even if we never hit the same city twice.”

Since Alaska allows up to 4 entries in a multi-city itinerary (not four legs — Alaska will add connections on its own as necessary), my itinerary IND-PDX-OGG-DCA wasn’t entirely optimized. I could have added a longer stopover in Los Angeles on the way back, or a longer layover in Seattle on our outbound itinerary.

Ultimately, because of Alaska’s strong North-South axis on the West Coast, a truly optimal itinerary would need to include several West Coast stops. For example, this is a valid companion fare itinerary:

  • JFK-SEA//PDX-SFO//LAX-LIH//OGG-LAX

You can put an unlimited amount of time between each of these legs, meaning as Scott points out, these are really “four one-way fares booked on a single ticket.”

Of course, that begs the question: why would you want to book four unrelated one-way fares on a single ticket? First of all, the fares don’t have to be unrelated. Our flights from Indianapolis to Portland, Portland to Maui, and Maui back home were not “unrelated,” after all. But even in the case of totally unrelated fares, there are reasons you might consider it.

Since Alaska prices out all itineraries as one-way fares, it’s not uncommon to find a situation where one leg of your trip is expensive with cash and cheap with miles, while the other leg is cheap with cash and expensive with miles. If the dates and directions all line up properly (no small feat), you could use a single companion fare to book four one-way fares, then fill in the rest of the itinerary with miles or cash as you see fit.

Likewise, especially frequent travelers might consider “nesting” different trips inside a single itinerary. Someone traveling frequently between Washington and Los Angeles, for instance, might book:

  • DCA-LAX//LAX-OGG-LAX//LAX-DCA

If you squint at this just right you see it’s actually two unrelated roundtrips: one between DCA and LAX, and one between LAX and OGG. To make this work you’ll need to book an additional roundtrip between LAX and DCA, of course, but in exchange you get can get two companion fares for the price of one.

Conclusion

Bank of America has added some restrictions in recent years to who is eligible for certain new credit cards, unfortunately including the personal Alaska Airlines Visa card. The business card is supposedly unaffected for now, so even if you don’t have any Bank of America Alaska Airlines cards you should be able to sign up for one personal and at least one business card, naturally conditional on your creditworthiness.

The main effect of those changes should be to discourage folks who already have multiple personal Alaska Airlines cards from cancelling them, unless they’re absolutely certain they won’t be flying Alaska anytime in the near future, since it seems that it will be increasingly difficult to collect new companion fares going forward.

Quick hit: when are you eligible for your first Hilton Honors Aspire American Express resort credit?

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I started writing this blog because I was frustrated by how imprecise and inaccurate the mainstream travel hacking bloggers I was reading at the time were. In some ways that situation has gotten a lot worse, as credit card affiliate blogs have consolidated and become ever more limited in what kinds of deals they’re able to talk about, while in other ways it’s improved, as more independent bloggers have started writing without relying on affiliate revenue.

As careful as I am to be as accurate and precise as possible, I got caught out on Wednesday by two commenters asking versions of the same question: when are you eligible for your first $250 Hilton Honors Aspire American Express resort credit? This is a question it genuinely hadn’t occurred to me to ask.

The source of the confusion

The reason my commenters were confused arises from the fact that the resort credit is described in at least 2 different ways in different places:

  • on the American Express credit card application: “With your Hilton Honors American Express Aspire Card, enjoy up to $250 in statement credits each year of Card Membership for eligible purchases at participating Hilton Resorts.”

  • on the American Express “benefits” tab for existing cardholders: “Upon renewal of your Card, enjoy $250 in Hilton Resort Credits each year when you stay at a participating resorts within the Hilton portfolio.”

This raises the question, is the resort credit an anniversary benefit (like the bonus Radisson Rewards points offered by US Bank, or the Alaska Airlines companion ticket offered by Bank of America), or an annual benefit? If it’s the former, the value of the card drops enormously, since the credit would only be available if you kept the card or were able to make an eligible resort charge shortly after your first anniversary. If it’s the latter, you have an entire year of card membership to find a chance to use the credit before canceling the card.

My answer to this very good question

I was so flummoxed by these commenters I started to believe I may have actually misunderstood the terms of the benefit, something that has happened before and will happen again (always for the benefit of my readers). Had I relied too much on the seductive prose of affiliate bloggers? Had I, the anti-affiliate-blogger, become a pawn in their game?

But I quickly oriented myself and realized my original interpretation of the benefit, that it is available during your first year of card membership, had to be correct for a simple reason: the card is less than a year old, and people have already received resort credits. The relevant FlyerTalk thread has datapoints from as early as March, 2018, less than 3 months after the card was launched, so the benefit has to be available during the first year of card membership.

Conclusion: banks and loyalty programs love to out-legal themselves

If you squint at the conflicting language just right, you can start to see what American Express and Hilton were thinking: they wanted to make it as clear as possible that unlike the card’s $250 airline fee credit, which resets on January 1 of each year, the $250 resort credit is a cardmember year benefit, and they tried to express that concept in slightly different, slightly contradictory ways. While lawyers have fun pretending to speak with precision, English simply isn’t a surgical language. Here’s my modest attempt at reformulating the resort benefit:

“Each year of card membership, beginning with your first year, and continuing each additional year upon the anniversary of your account opening, enjoy $250 in Hilton Resort Credits each year when you stay at a participating resorts within the Hilton portfolio.”

As always, you can find my personal referral link on my Support the Site! page (feel free to use either my Hilton or Delta referral link, since they should both give you access to the same cards).

The great, good, weird, and apologetic about the Grand Wailea, a Waldorf Astoria Resort

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What a week! I bring you alohas (that means “hello”) from Maui, the second largest island in the state of Hawaii (or as the locals call it, “the aloha state”). As a reminder, I organized this trip as a belated honeymoon taking advantage of a few interlocking opportunities:

  • Hilton Honors offers the fifth night free on award stays to all elite members (everyone, in other words), which is naturally most valuable on stays of exactly 5 nights at top-tier 95,000-point properties;

  • the new American Express Hilton Honors Aspire card offers a $250 statement credit for charges made at “participating Hilton Resorts;”

  • there’s also currently an Amex Offer for a $70 statement credit when you spend $350 at Waldorf Astoria Hotels & Resorts in the US, Amsterdam, Berlin, Edinburgh, and Paris and Conrad Hotels & Resorts in the US;

  • and the Bank of America Alaska Airlines companion ticket can be used to book moderately complex multi-city itineraries with a stopover, so we were able to use it to fly from my partner’s family in Indiana, to my family in Oregon, onward to Maui, and back to the East Coast, all for the price of a single Alaska Airlines ticket, plus taxes and fees.

There are a few ways the deal could have been stretched a little further. For example, I booked all five nights from my Hilton Honors account, including this weekend, while it would have been technically optimal to book a 5-night stay ending on a Friday night, then use the Aspire card’s free weekend night certificate to book a free 6th night and my Ascend free weekend night certificate for a 7th night, but that would have required my partner to take a lot more time off work, and we’ve already been traveling since before Christmas. As a rule I try to avoid organizing my travel around stunts unless I think I’m going to get a particularly good blog post out of them, and the free weekend night certificates will certainly get used, hopefully at a good redemption value.

The Grand Wailea breakfast mystery, solved

When I first wrote about this trip, I explained that I’d been told the Diamond breakfast benefit was “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]. But I’m now happy to be able to share the actual letter describing the benefit I was handed when checking in last Wednesday:

Breakfast, revealed!

Now, a civilian might think this letter is as clear as day: a $30 per day credit for food and beverage. But if you’re a travel hacker, you know this raises just as many questions as it answers. What’s a “day?” We arrived on Wednesday afternoon and departed on Monday; do we get six $30 credits, one per “day,” or five $30 credits, one per night of our stay? Is the credit “use it or lose it,” so we have to spend $30 per day, or can we splurge on one day?

I asked all these questions to our check-in clerk, and was told, “I don’t know, it doesn’t matter, we’ll just take $150 off your bill when you check-out.” And sure enough, when we checked out yesterday the front desk agent was happy to remove $150 from our room charges (although I did have to remind her, possibly due to the chaos the night before — see below).

The property is spectacular, but starting to show its age

Before arriving, I requested a quiet room, and we were given a ground floor king room in the “Chapel Wing,” with a balcony overlooking one of the resort’s many koi ponds. The room was indeed quiet, except for in the mornings when housekeeping carts rattled by on the tiles outside and the sprinkler system turned on to water the gardens. The room had a small refrigerator instead of a minibar, which was great for storing food, leftovers and drinks, which we found very convenient.

While everything in the room was great, it was the first place we started to notice wear and tear on the property, which opened in 1991 and underwent a major renovation as recently as 2017. At some point the door handles were replaced with longer, curved handles (possibly as an ADA compliance measure?), but the raised decorative designs on the doors were not taken into account. That means our door handle didn't have a full range of motion, and the bolt didn't fully withdraw when we turned the handle from the inside. Nine times out of ten, this doesn’t matter and the door closes anyway. The tenth time, the bolt catches against the doorframe and the door stays open. We noticed this happen one time and pulled the door shut on our way out, but the second time it took a a security guard to notice it, who promptly scared the daylights out of us when he walked into the room to make sure we were ok! Other than that, we mostly noticed small things like missing tiles in the swimming pools and chipped paint on the waterslides, but nothing that interfered with our fun.

Speaking of fun, the main attraction at the resort is its network of swimming pools and hot tubs, most of which are connected by waterslides, so you can start at the top level and slide down from one level to the next, or take one long fast ride all the way to the bottom. I don’t know why some people don’t like resorts with kids, but if you’re one of them, you are not going to like this place. There is one "adults-only” pool, but it’s right in the middle of all the other pools so there are still kids walking through all the time to get between the waterslides and the guest rooms. I guess they’re just not allowed to actually get into the water. Compare that to the Hyatt Zilara, where it was someone’s full-time job to keep kids from stepping over a rope onto the “adults-only” portion of the beach.

The adults-only Hibiscus Pool

Paying for (and eating) the food

I had my partner sign up for an Aspire card before this trip, so we had a $250 American Express credit (remember: this is a cardmember year, not calendar year, benefit) to spend in addition to the $150 food and beverage credit. Plus, since she had the $70 off $350 offer on her card, if we spent a total of exactly $500 we’d end up owing just $30 after the $150 property credit, $250 Aspire resort credit, and $70 Amex Offer credit.

Based on our experience at the Hyatt Zilara Rose Hall in Jamaica (an all-inclusive resort, so we didn’t actually spend any money there), I assumed we’d be spending a lot more than that, so I planned to charge any amount over $350 to my own Hilton Honors Ascend American Express to trigger another $70 credit. That ended up not being the case, for two main reasons: the food at the Grand Wailea isn’t very good, so we didn’t eat very much of it, and the Grand Wailea isn’t nearly as isolated as the Zilara.

In fact, there’s a shopping mall with a pair of grocery stores (same company, but with slightly different selections) just next door, so we were able to stock up on drinks, snacks, and even things like salads and sandwiches there and pay perfectly reasonable prices. Many of the prices didn’t even seem inflated compared to prices on the mainland, and Hawaii has a state sales tax that’s less than half what we pay at home.

Ultimately, when we woke up Monday morning, we still had over $50 left to spend to get up to $500 total, but we went for a morning swim and managed to run up a bill poolside to cover the difference.

Before I go any further, let me be clear that it’s perfectly possible to spend as much as I had expected to at the Grand Wailea. Importantly, we didn’t take advantage of the four luxurious options on the property: the fine dining Humuhumunukunukuapua’a, the Sunday brunch at the Grand Dining Room Maui, the Luau, or the “sunset cabana dining” option. We also didn’t order room service, which has both a $7 delivery charge and a 20% service charge. If you do any combination of those things, you’ll have no trouble triggering as many statement credits or minimum spend requirements as you please; entrees at “Humuhumu” are between $34 and $95, and sunset cabana reservations cost between $685 and $2,235 per couple (which at least is inclusive of taxes and tip). I don’t have anything to say one way or the other about whether you should try one or all of those options, I can only say I didn’t save $8,000 on my stay in order to spend it on food and drink; I saved $8,000 on my stay because I don’t have $8,000.

With that out of the way, we did eat at three on-site restaurants:

  • Café Kula. This was our go-to for breakfast, and we also ordered one lunch and a couple dinners there, all of which were basically a mixed bag. The "avocado toast” was guacamole on stale bread and the “kale burger” was a vegetarian burger patty on a bed of raw kale leaves. On the flip side, the "Wailea burger” was the best thing I had at the resort (I ordered it again our last night just because I was tired of being disappointed), and the “wild mushroom pizza” was very weird but not in a bad way at all, and if we return I’d happily try out some of their other pizzas.

  • Bistro Molokini. We had our only sit-down dinner of the trip here, and my partner thought her tofu dish was pretty good, but the real stars were the sides of asparagus and mashed potatoes we ordered. My “Hamakua Springs Bibb Lettuce” salad was a disaster, first because they gave me the identically named salad off the regular menu instead of the vegetarian menu, which wasn’t a problem, except the chef also forgot to put avocado on it, which was literally the only ingredient costing more than $0.50 in the whole $20 dish. When I pointed this out to our server she first tried to tell me that “sometimes the chef cuts the avocado so small people don’t know it’s there," but finally had to concede that there was obviously no avocado on my salad and took it off our bill.

  • Hibiscus Pool. Our final morning we ordered some onion rings off the adults-only Hibiscus Pool menu, and not only were the onion rings pretty good, once I’d taken a look at the menu I decided it might be the best “restaurant" at the resort! On the flip side, one day at the pool I overheard a waitress enthusiastically apologizing to another guest because his burger had tomato on it, which he had asked to be left off.

And that’s the vibe I got from virtually all our interactions with staff during our stay: enthusiastically apologetic. The security guard was apologetic our door was broken, the maintenance guy was apologetic our door was broken, our waitress was apologetic my salad was broken, the bartender was apologetic my cup was broken, the morning of our departure the housekeeper was apologetic for barging in on us (the one time I almost lost my temper pointing out the privacy sign on the door to her), and everyone worked hard to try to make things right.

And of course everyone was apologetic on our last night when a nearby transformer exploded and wiped out power to the entire area, with the convenient exception of the Grand Wailea’s Chapel Wing, where we were staying. When we walked up to the lobby bar for a nightcap we discovered folks were making the most of it, and the hotel was accommodating everyone with some portable emergency lighting equipment, seen here:

Desperate times = desperate measures

A note on transportation

I bounced around several times when deciding on what to do for transportation on the island. My preliminary plan was to rent a car for our entire stay at the airport and pay for parking at the hotel. Ultimately things ended up a lot simpler than that:

  • I paid $49.50 for a “shared” SpeediShuttle reservation for two from the Kahalui airport to the resort (although we were the only passengers);

  • On Friday, we paid about $34 each way to take a Lyft to and from Wailuku for the Friday Town Party;

  • On Sunday I paid $150.20 to rent a Jeep for the day from the Enterprise rental car desk at the Grand Wailea to drive up to Haleakala National Park;

  • Finally, on Monday I paid $38.13 for an Uber back to the airport.

There are two tricky things to note here. First, Lyft and Uber can drop off at the airport, but can’t pick up passengers there, so you slightly overpay for a shuttle to the Grand Wailea compared to the ride back.

Second, as convenient as it is to be able to pick up a rental car directly at the hotel, be careful when making an Enterprise reservation. The desk opens at 7:30 am, so I made a reservation for 7:30 am each morning we were there, assuming we’d only end up using one or two of the reservations. On Saturday we stopped by the desk around 9:30 am and were told they’d given our car away (which I was expecting) and that they’d have to give us a different vehicle (which I was expecting) and that they’d have to charge us $60 for the upgrade to a Jeep (which shocked me). I turned down the offer, went back to the room and changed my Sunday reservation to 9:30 am (for the same price).

Sunday morning we went by the desk at 9:30 and not only did they still have the car we reserved, but offered to upgrade us to a Jeep for $20, which I gladly accepted. I know rental agencies famously operate on slim margins, and I’m not even really upset they tried to gouge me on Saturday, but my word of warning is to make your reservation for the time you actually expect to get going in the morning, instead of the time the rental desk opens, so they don’t have an opportunity to rip you off.

One fun thing about myself I learned on this trip is that I thought I hated driving, but it turns out that was just because I’d never driven a Jeep before. They’re extremely fun.

We be wrangling

Conclusion

I hope this doesn’t sound like a “negative review” or anything like that. Our room was great, the weather was perfect the entire time we were there (until it started to drizzle on our way to the airport, just in time to help the firefighters working on the blaze started by the aforementioned transformer explosion), and we got to spend hours swimming, reading and playing in the resort’s terrific waterpark. But, we also made some obvious mistakes (“kale burger”) that hopefully this post will help readers avoid if they ever decide to check out this top-tier Hilton Honors redemption for themselves.

I’m not a tour guide, but we did spend a couple days exploring outside the resort, so I’ll try to write up a few brief suggestions for other things to consider checking out if you do find yourself at the Grand Wailea anytime soon.

Just another day in paradise