What the New York Times got wrong about long-haul Amtrak travel

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Last week’s New York Times Magazine featured a long article about long-haul Amtrak travel that somehow managed to get almost everything wrong about the advantages and disadvantages of train travel. As a life-long enthusiast of train travel, I thought it might be helpful to correct some of the more common and absurd myths perpetuated in the article.

Myth #1: Amtrak travel is expensive

Behold the feigned horror the Times Magazine author imputes to her hypothetical friends:

“Depending how you slice it — time or money — there are either 61 or 960 immediate reasons not to travel by Amtrak trains from New York City to Los Angeles. Those are the extra hours and dollars, respectively, that you might reasonably expect to forfeit if you forgo a six-hour $129 nonstop flight and opt instead for an Amtrak sleeper car. Covering the interjacent 2,448.8 miles can easily consume some 67 hours for a mind-boggling $1,089.”

Unfortunately for the Times Magazine, these numbers are easily checked. For non-stop flights between New York City and Los Angeles 6 months from now, I actually found slightly cheaper economy flights than the ones that Weaver reports, starting at just $127:

But the identical Amtrak route she took between New York City’s Penn Station and Los Angeles’s Union Station doesn’t cost $1,089. It costs just $232:

Why the difference? Because Weaver is comparing Amtrak’s sleeper car accommodation to American Airlines’s economy cabin (I actually found sleeper car accommodation on the same date in October not at $1,089 but at $914 — Weaver should start booking further in advance!):


The deliberate confusion of economy-class airline fares with sleeper car Amtrak fares is journalistic malpractice, but that doesn’t stop us from untangling it a little bit more.

First, let’s take note that an economy-class airfare between New York City and Los Angeles International Airport requires you to travel to one of New York City’s regional airports from your residence, and from LAX to your final destination in Southern California. I don’t live in New York City or in Los Angeles, so I’m not going to pretend to venture a guess at that final cost, besides spitballing that it’s in the high 2 figures, depending on your origin and final destination. Remember you’re only working with $105 in “profit“ to begin with by flying instead of taking Amtrak.

Second, what do you get for your fare in each case? In the case of the airfare, you get the convenience of same-day arrival. In the case of Amtrak travel, you also get 3 nights of accommodation on board the train. If we insist on only comparing airfares and Amtrak fares, that leaves you paying $35 per night for a place to sleep (assuming in each case that your flight and your train arrive on time — no sure thing). Amtrak also includes free checked bags and much more in-cabin storage space than the typical US airline, a potential additional source of savings.

Of course, I don’t recommend traveling on long-haul Amtrak routes in coach. The sleeper cars are far preferable! That brings us to the third piece of the cost puzzle: sleeper car accommodations include the same 3 nights of sleep, but on what an airline blogger would insist on calling “lay-flat seats,” plus 9 cooked-to-order meals in the Amtrak dining car (dinner on day of departure, 6 meals en route, breakfast and lunch on day of arrival).

For a single traveler between New York City and Los Angeles, we can finally make a clear comparison: $127 is the underlying cost of transportation, with the option to pay $262 per night for three hot meals per day and private sleeping quarters.

Is that a good deal or a bad deal? Well, that depends on how much you planned to pay for room and board in New York City and Los Angeles, which I’m in no place to judge. But the math changes a final time when you book a sleeper car with multiple people, as intended.

That’s because when you travel on Amtrak, you pay a fixed price for each sleeper car room, up to the maximum number of passengers that room type accommodates. The cheapest roomettes on this route accommodate two passengers, which means two people can buy 3 nights of room and board for a total of $892, or $446 each, $149 per day (remember we’ve assigned an underlying value to the transportation itself of $127 per person):

Suddenly it become clear that when used as intended, Amtrak long-haul travel isn’t outrageously expensive. Booked far enough in advance, it starts to look like a steal.

Myth #2: Amtrak travel is inconvenient

Weaver gave herself a bit of an unfair advantage by selecting a particularly illogical route to go by train: between two cities served by multiple airports and multiple airlines, but only an awkward train connection. Personally, I would not book an Amtrak trip with just a 5-hour connection window, as hers does in Chicago. In the waning days of the old Amtrak Guest Rewards program I booked an itinerary from Chicago to Los Angeles on the Southwest Chief, connecting to the Coast Starlight. Over the next 3 days the train was predictably delayed, we missed our Coast Starlight connection, and had to be rerouted by bus and regional rail upstate to where the Coast Starlight ultimately caught up to us.

But there are lots of routes where Amtrak is not only convenient, but indispensable. Someone living in Seattle or Portland who wants to take a New Year’s ski vacation at Whitefish Mountain Resort, near Whitefish, MT, can sit down on New Year’s Day on the Empire Builder at 4:40 pm and arrive in Whitefish the next morning at 7:21 am for $77; they could be on the slopes by 9 am. The next best alternative I found is a $139 Alaska flight, not to Whitefish but to Kalispell, arriving at midnight (requiring another night of lodging), and a 15 mile car or shuttle to Whitefish. Which do you think is more convenient?

Now head the other direction: 6 months out, you can book a 7 hour, 47 minute flight from Chicago to Wolf Point, MT, for $381 per person, with (pretty tight) connections in both Denver and Billings. Or you can sit down on the Empire Builder at 2:15 pm and arrive in Wolf Point around noon the next day for $110. Which do you think is more convenient?

Let’s do one more fun one. If you want to get from Mattoon, IL, to McComb, MS, you can drive 2 hours to Indianapolis International Airport, pay $94 to fly to New Orleans, connecting in Atlanta, then drive another 2 hours or so to McComb. Or you can sit down on the City of New Orleans in Mattoon and step off in downtown McComb 13-and-a-half hours later for $111. Which do you think is more convenient?

You can see from these examples the obvious convenience of Amtrak, and train travel in general: it makes the intermediate stops that other forms of long-haul transportation don’t. To put it another way, Amtrak is only inconvenient if you aren’t using it as intended. For folks without impaired mobility, It’s incredibly inconvenient to ride a municipal bus two blocks. You have to find the right stop, figure out whether a bus is a local or express, wait for it to come, then it might drop you off on the wrong end of your destination block. How inconvenient! But that’s because you’re using it wrong, not because municipal buses are an outdated or unnecessary form of transportation.

Myth #3: There is No Reason to Cross the U.S. by Train

Near the beginning of her article, Weaver notes in passing:

“The most unifying characteristic of my fellow passengers was not age (although, as a rule, the sleeping cars skewed retired), race (very mixed), income (while sleepers are astronomically priced, coach seats can be downright economical for shorter segments) or even fear of flying (no one I spoke to had it).”

This is best understood as a passive-aggressive swipe at a 2013 Times article about Amtrak travel, which explains perfectly clearly why people take Amtrak: if you have a fear of flying, you have a fear of flying no matter how much longer train travel takes. If you’re unable to fly for medical reasons, you’re unable to fly no matter how much cheaper it would be. If you’re undocumented, you’re unable to fly (and often unable to drive) no matter how much more convenient it would be. Train travel doesn’t serve those populations as a “backup” option; it serves those populations as the only option.

Conclusion: if you don’t like train travel, don’t travel by train. But don’t tell me there’s something wrong with trains

I’m perfectly aware of confirmation bias, and the fact that I love train travel obviously makes me seek out the most convincing arguments in favor of train travel. If you think train travel is a poor substitute for flying or driving, then you won’t find these arguments convincing.

Writing this post, I was reminded of my notorious screed about Galveston, TX, where I wrote extensively about how hard it is to get there, and reader stvr commented, “Do you not have a driver's license?” To stvr, renting a car for a weekend is a totally normal and good way to get around, whereas to me it’s an almost unfathomably annoying prospect.

Whether it’s flying, car rental, or train travel, issues where people have strong feelings are opportunities for disagreement, but also a chance to exercise some epistemic humility. I hate renting cars, but I’m not crusading for the destruction of the car rental industry; I know that many people believe it serves a useful function, and I’m not willing to say with certainty that those people are wrong. Likewise, even if you hate traveling by train, before destroying America’s passenger rail network once and for all, do me a favor and take the opportunity to step back and ask how certain you really are that all of us who love it are wrong.

Disputing derogatory remarks with Experian, a developing story

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If you entered the travel hacking game through the big credit card affiliate bloggers, you probably know that folks who rely on credit card signup bonuses to build their points balances closely monitor and protect their credit reports, sometimes going to outlandish lengths like paying off credit card balances before their statements close, hoping that low reported balances will make them ever more creditworthy, eligible for more exclusive cards and higher credit limits.

Since I earn the overwhelming majority of my miles and points through manufactured spend, I find these antics to be mostly amusing (and mostly harmless). Indeed, since I aggressively take advantage of offers like the Chase Slate introductory $0 balance transfer fee and 0% APR on balance transfers, my credit utilization rate is often at or above 90% on one or more of my open credit cards.

That doesn’t mean I don’t really screw up sometimes: I recently discovered Barclaycard doesn’t allow you to make same-day payments after 8 pm Eastern time, which left me paying my balance off a day “late,” with Barclay’s cheerfully chalking a late payment up on my credit report.

However, I recently found a much more serious derogatory remark on one of my credit reports, which I decided to dispute.

Reminder: which credit cards monitor which credit reports?

There are three major credit bureaux, and each calculates a separate FICO score based solely on the information reported to that bureau. While a number of banks and credit cards now offer free access to your FICO score, each typically partners with only a single bureau. That means to get free access to all your FICO scores, you need to know which credit cards track which bureaux:

  • Experian: Chase Slate (FICO)

  • TransUnion: Chase Slate (VantageScore), American Express (VantageScore), Discover (FICO), Bank of America (FICO), Barclaycard (FICO)

  • Equifax: Citi (FICO)

As a victim of the Chinese cyberattack on the Office of Management and Budget, I also have free access to MyIDCare, which monitors all three credit bureaux and alerts me to any changes on my reports (and a bunch of sillier stuff like when sex offenders move into my neighborhood).

The credit union, the negative balance, and the charge-off

Back in November or December of 2018, I started getting automated calls from a credit union I had experimented with for a manufactured spend liquidation strategy, telling me my account had a negative balance and asking that I call back immediately.

When I did, the young man on the other end told me a complicated story about my account being mistakenly credited multiple times for the same transaction, all the way back in the summer of 2018. Since I had withdrawn the money already, when the credit union discovered the “error” and debited my account, it created a negative balance they were now trying to collect.

This all seemed quite plausible. The only problem was, the young man was unwilling to provide any documentation of this curious series of events. The amount of money involved wasn’t enormous, but I have a general principle to not give people money unless they can have some sort of evidence that they’re actually owed it, the subject of a delightful book about the financial crisis by the journalist David Dayen, “Chain of Title.”

Disputing Experian derogatory remarks is fast and easy

That brings me to this February, when MyIDCare reported that a new derogatory remark had appeared on my Experian credit report: the credit union had charged off my negative balance. Interestingly, so far the charge-off has been reported only to Experian, and my other scores haven’t been affected (keep in mind they were nothing special to begin with).

Since the credit union had never been able to provide any documentation, I decided this would be an interesting opportunity to learn how to dispute credit information. And it turned out to be a breeze!

A simple Google search took me to Experian’s main dispute page. At this point, you have the option of creating a “free” account or a “limited” account. This is a little bit confusing because neither account costs any money. The difference is the “free” account is used to upsell you additional Experian services, while a “limited” account is used only to dispute items on your Experian record. I created a limited account.

This took me directly to the Experian Online Dispute Center, and my new charge-off was sitting right at the top of the page. After selecting it, I was given five dispute options:

  • "Payment never late”

  • “Not mine or No knowledge of account”

  • “Account paid in full”

  • “Account closed”

  • “Unauthorized charges”

I thought “Unauthorized charges” most closely resembled my complaint (since I’d never authorized the debit), so I selected that. On the next page, a comment box let me explain what happened in a few words, and then I submitted the dispute. The whole process took perhaps 10 minutes.

Conclusion

I’ve heard horror stories about how difficult it is to remove false information from a credit report, and indeed I’m not particularly optimistic that I’ll succeed in having the charge-off removed. On the other hand, I’m fairly impressed with how streamlined Experian’s dispute process is, so if you’ve been dreading figuring out how to dispute derogatory or incorrect information on your credit report, take heed: it’s easier than you think.

Experian estimated the dispute would take about a month to resolve, and I’ll keep readers updated as the situation develops.

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).