You booked early. You compared prices. You lined up the rental car, the flights, the hotel, even the points. You did what experienced Hawaii travelers are supposed to do. Then something quietly went wrong anyway.
Over the past year, we have seen this pattern repeat across the islands. The problem is not bad planning. It is that many of the familiar rules people rely on no longer match how Hawaii travel actually works right now.
That advice still works in many places. In Hawaii today, it often does not.
Relying on loyalty programs may get you nowhere.
Generic travel advice treats highly hyped and hugely profitable loyalty programs as stable, long-term assets that reliably benefit travelers. Hawaii travelers are discovering that those assumptions no longer hold.
On October 1, 2025, HawaiianMiles officially ended and was absorbed into Alaska Airlines’ new Atmos Rewards program. Flights, apps, and accounts consolidated. On paper, the transition is complete. In practice, many travelers are still navigating confusion around benefits they assumed would carry over. Companion certificates, upgrade paths, partner access, and familiar elite perks have changed or disappeared. Travelers who booked trips expecting HawaiianMiles rules found themselves operating under a different system by the time they flew.
Generic advice says “join the program,” every program. It does not warn you that in Hawaii, the program you joined may not exist in the same form by the time your trip arrives, or may not benefit you at all.
Beyond the turbulence of the merger, loyalty itself has become far harder to justify. Based on our own experiences, it delivers far less than it used to. In Hawaii, the gap between loyalty in theory and loyalty in practice is impossible to ignore.
Airline loyalty used to reward frequency. Today, it increasingly rewards spending. For travelers paying their own way, that shift matters. Status thresholds have risen, award pricing is dynamic, and perks that once felt meaningful are now often sold a la carte anyway. Many travelers still belong to multiple programs, but wisely, fewer are building trips around them. Price, schedule, and flexibility have quietly moved to the front of the decision-making process.
Hotel loyalty breaks down even faster in Hawaii, where pricing disparities can be extreme. We recently planned to stay at a Hilton resort and fully expected to book directly as members and frequent guests. Instead, we ended up booking through Booking.com, earning no points. The reason was simple. The Booking.com rate was about half the Hilton member rate for the same stay. No joke. Shopping pays. Loyalty does not.
At that point, for us, loyalty stops being a strategy and becomes a penalty. Points are a promise of future value. A massive price difference is cash saved right now. In Hawaii, those gaps can be so significant that the math is no longer even close, and the traditional advice to “book direct, save and stay loyal” utterly collapses.
That is the pattern we keep seeing. Travelers are not abandoning loyalty out of spite or rebellion. They are simply doing the math. They still join programs, but they are no longer willing to pay a premium to keep a badge alive. In Hawaii, especially, savvy travelers know that loyalty increasingly means loyalty to your wallet today.
The same is true with air travel. We used to count on mileage or loyalty upgrades reliably. We have largely abandoned that approach and instead try to buy what we expect to get from the outset. If we want business class, we find the cheapest business class with the best service. Done.
Book your rental car early can be misleading.
This is one of the most repeated travel tips anywhere, and in Hawaii, it is technically correct yet dangerously misleading. On the mainland, “early” often means a couple of weeks. Inventory is deep. If prices drop, you keep rebooking. If something goes wrong, there is usually another option nearby. But not always in Hawaii.
In Hawaii, early means 60 to 90 days or longer, especially during high seasons, holidays, and school breaks. Rental fleets never fully recovered after COVID, and inventory tightens more quickly than even regular Hawaii travelers realize. The familiar mainland strategy of waiting to see if prices fall can seriously backfire here in ways that feel disproportionate.
When a rental car falls through in Phoenix, it is a minor inconvenience. When it falls through on Maui or Kauai, it can mean the trip no longer works at all as planned. There may be nothing else available, as we just found, or what remains is so expensive that it changes the entire cost of the vacation.
The advice is not wrong. It is incomplete for a market where hesitation carries real, distinct risks.
Just rebook if prices drop can fail.
This strategy works best in markets with elastic supply. Hawaii, by definition, is not one of them.
Here, lodging and rental inventory move in feast-or-famine cycles. When availability is plentiful, prices soften, and rebooking can work. It still does. We’ve done that even recently. When demand surges, inventory disappears quickly and often does not return.
Travelers who cancel in hopes of saving a little sometimes discover they have canceled themselves out of the market entirely. In most destinations, that gamble costs time. In Hawaii, it can cost the trip.
That asymmetry is the point. Advice that fails elsewhere fails mildly. Advice that fails here fails completely.
The common thread is not bad advice. It is changed conditions.
Hawaii right now operates with tighter inventory, evolving airline systems, and far less margin for error. When something breaks, there is often no easy workaround waiting down the road.
Generic travel wisdom was built for places where abundance smooths mistakes. Hawaii today runs on constraint. That does not make it unwelcoming, but it does mean the old rules carry more risk than travelers expect.
What travel advice worked for you everywhere else, but backfired once you landed in Hawaii?
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Excellent article, and I agree completely with your advice and tips. Your comment regarding the only loyalty that matters is the loyalty you have to your wallet is spot on. We have lifetime elite status with both airline, hotel, and rental car companies, but we always book where we save money no matter what. The only status and loyalty that matters is the status and loyalty you have to your wallet once you’ve purchased the trip. You, the Traveler, are the only person who has an interest in your financial well-being, so plan accordingly, be smart, and look out for yourself and your family when making travel arrangements to Hawaii. No one else is going to do it for you.
Aloha to all.
I totally agree with your assessment of planning. Loyalty has changed, and now it just means loyalty to yourself, period.
Additional suggestions, besides booking.com which I use, expedia.com for car rentals and book early with no down free cancel. Price drops, rebook, same format.
Same thing with airbnb, but half down, free cancel.
The only odd thing I do is when going out of country, I have insurance on my trip. Say $2k trip coverage worth, but the intent is the medical and mainly for emergency transport back home. I’m 72, it’ll cost a fortune to get home so $1m transport coverage with Allianz. Costs $400 for my wife and I.
The article’s gripe really applies everywhere nowadays: “The [Insert Destination] Trip You Planned Right Still Goes Wrong.”
I generally book placeholder reservations for hotels and rental cars (cancellable) almost everyplace I go. That goes for the USA and foreign travel. Then I just keep searching for something to beat it. I’ve found Costco Travel great for rental cars but I generally use booking.com or the direct hotel sites (since I’ve signed up for their programs even though I don’t have status) for accommodations. Regardless of my bookings, I continue to search.
For airline flights, I generally use Google flights to get me a feel for my route choice costs. I use the subscription versions of PointsPath (with their Chrome Add-in extension) and seats.aero to search for airline award flights. Just finding one cheap award flight pays for each subscription.
Traveling anywhere, **not just Hawaii**, requires research and vigilance “to find something better.” Good luck!
We’ve had good luck with Costco Travel for cars and sometimes hotels and packages, but airline loyalty has never really paid off for us. I don’t miss worrying about status anymore. It was mostly useless.
I plan trips months in advance and enjoy the research. I’ve almost always done better separating flights, hotels, and cars instead of booking packages or relying on points.
We used to chase airline miles aggressively. At some point it felt like work with quickly diminishing returns. Now we just buy the best nonstop.
We’ve booked almost exclusively through Booking.com and sometimes Hotwire for years and rarely book direct anymore. Loyalty programs never seem to beat the price, especially in Hawaii. Points are nice in theory but cash savings matter more to us.
We keep coming back because we love Hawaii, but it definitely takes more effort than it used to. You can’t just rinse and repeat old plans as we did for so many trips. Now each one works differently.
I still like having points as a backup, but I don’t plan trips around them ever anymore. If they work, great. If not, I’m not surprised or disappointed and move on. Totally different than before.
The loyalty section is spot on. I finally stopped chasing airline status last year and just buy the flight I want now. It’s honestly way less stressful and I’m happier.
We still use loyalty programs selectively and sometimes they work out well, especially if we book far in advance and stay flexible.
We researched and thought we did everything “right” for our last Maui trip and still got burned on hotel pricing and car rentals. It felt like the rules changed.
The only reason prices drop is because of excess inventory. No one has a 30 day price guarantee and if they did everyone would ask for the difference. If you discount cars, rooms, etc to fully sell out then your have to take in account how many other people get the same alerts other than yourself. How do these people know when prices rates drop? Google alerts? Flip a coin. Do you feel lucky? Easy to play this game if you already reside in Hawaii.
How much of this supply/demand is weather related? IMO I think airlines vacation sites get so many floors of rooms allocated to only their marketing groups. Same as car rentals only reserved for vacation package shoppers. As far as direct hotel booking you know you have a room as opposed to a online travel agency that has mistakenly overbooked the property. I have seen where tourist’s book OTA’s and getting to the hotel the front desk person informs them that they don’t show any reservation that went through. That’s why I always call the hotel directly after and confirm. Like I said this cancel rebook process works if you can afford 2 bookings and cancel the more expensive after obtaining the cheaper.
Great article regarding the Hotel stays.
We recently booked and stayed at the Outrigger Paradise Hotel and found the on line price for our stay $400. cheaper.
We have been staying at this Hotel for more then 20 years and belong to Discovery their royalty programmes which they say best price guarantee.
This has made us sad as no more visits to Hawaii.
Read your articles with great interest.
Never book through Booking.com. They are thieves.
Give us an example why they are thieves, please…..
I have been booking through Booking.com for stays all over the western hemisphere for over a decade and have never had a problem. Indeed, I’ve nearly always gotten the lowest price (I find that only Hotwire can occasionally beat them).
While we were Starwood Preferred for many years and had a Hawaiian Airlines credit card for a couple years, we have never had brand loyalty. We go with whoever gives us the best deal. That usually means starting with Hotwire, Trivago, Kayak or VRBO and then checking the hotel chains directly to compare.
It has been rare that a loyalty program has gotten us a better deal on either flights or rooms.
I can also nearly always beat ‘packages’ by separating rooms, flights, cars and activities.
Of course, I have plenty of time to plan our trips and enjoy the challenge of getting a good deal.
On the other hand, there are many who are willing to pay more for convenience.