How we booked a 5-star luxury trip to Hawaii for over 50% off

We'll be staying here.
We’ll be staying here.

This April will be the hubby and my 2nd anniversary, and since we celebrated our 0-anniversary and 1-year anniversary with trips to tropical places, it seemed only appropriate to do it again this year as well. Having already done Mexico, the Virgin Islands, the Bahamas, and Belize, we figured maybe we’d give Hawaii a whirl.

And of course, since it was me, the goal was to plan an ultra-luxe trip with the minimum pricetag.

So, we started with flights.  At the time of booking, I had about 50k United points, 160k Chase Ultimate Reward points, 50k Starwood points, and 37k JetBlue points that I’d obtained through credit card offers, spending, and work travel. With that we could have transferred 110k UR points to United and had the 160k points we’d need for two round trip Saver-level business class flights to Hawaii – but after some research, it seemed that wasn’t the way to go.

Pretty much all the airlines flying to Hawaii are doing so with smaller, older planes that don’t offer lie-flat seats in business class.  And if you can’t lie-flat (and therefore, sleep) on your red-eye return flight…what’s the point of business class at all? Meanwhile, HawaiianAir offers their “Extra Comfort” (think: Economy Plus) product for a relatively small upcharge, for a total of $1,592 RT for both us. As such, spending 160k of my points for the same trip would have only gotten us a points value of $0.009 (9/10ths of a cent) which is pretty paltry.  One of my favorite mileage blogs, The Points Guy, advises you should be able to get a value of 1.5 cents per point for United points and 2.1 cents per point for UR points.

Because of this, we decided we’d be better off buying the Hawaiian Air flights with our Chase Sapphire card.  Because that gets us 2pts per dollar spent on travel, we’ll earn over 3,000 UR points.  Plus, because we aren’t likely to go to Hawaii anytime again soon, we were able to register to earn JetBlue points on the flight in place of Hawaiian miles, which will net us about 4,000 JetBlue points EACH round trip.

This is just a good example that flying for free, just because you can, isn’t always your best use of points.  

That left us with 50k United points, and with a little patience and persistence, I was able to secure the positioning flights we wanted, Austin to Los Angeles, for both of us, round trip, for free at the saver level – costing exactly 50k United points.  This was a savings of $572, total.

Up next, I began the research on hotels.  Here, since I hadn’t used my UR rewards to buy my flights, I had plenty left to use on hotels.  I transferred 100k points to my Hyatt account in order to redeem them for a 4-night stay at the Andaz Maui, a 5-star resort in Wailea that retails for $569 a night. Savings: $2,276.

We wanted to see more than just Maui, though.  We wanted to see black sand beaches and volcanoes.  So that meant a few days on the Big Island as well.  After booking a couple inter-island flights (cost: $402, total), I started looking into hotels. Initially, we were planning on using 30k Starwood points to stay at the Sheraton Kona, but after reading several not-so-positive reviews, we decided to look elsewhere.

And we're also staying here.
And we’re also staying here. (Photo credit

A bit of research brought us to the Fairmont Orchid, a 5-star resort in Kohala, and as it turns out, they were running a 30% off special for booking 3-months or more in advance.  That alone reduced down the $419/night prices to $293/night. Savings: $378.

But I wasn’t done.  After booking, I emailed the Fairmont Presidents Club to ask for a status match, since I have gold status on SPG.  As it happens, the Fairmont program doesn’t offer a status match, but they did gift me a one-time room upgrade certificate for writing in – which I was able to apply to move us up from a garden view room to a partial ocean view room, for no extra charge.  Savings: $63.

And while I was busy writing Status Match emails, I sent one to Hawaiian Airlines too, informing them of my status with Southwest, Jetblue, and Virgin America.  As a result, they granted me Hawaiian Gold status, which includes 2 free checked bags on each flight.  Savings: $50

Of course, I also have the United credit card.  That gives me free checked bags on my United flights, but also gives me two free United club passes a year – which we’ll use during our four hour layover in Los Angeles. Savings: $150

So, if you’ve been keeping track, we’re spending $2,873 but SAVING a total of $3,489 on our anniversary trip to Hawaii. That’s a 55% savings – which means we’re able to stay in five-star resorts and put more money towards activities and meals than we would had we just purchased everything ourselves.

And even better, we still have a ton of points left – 50k Starwood, 35k JetBlue, and 60k+ Ultimate Reward points – meaning that this trip to Hawaii doesn’t have to be our only trip of the year. So while some may mock my travel hobby, if a beautiful vacation in Paradise is my reward for being a bit obsessive about miles and points, that’s a trade off I’ll take any day.


Author: Mrs. Millennial

I'm Whitney, writer of Mrs. Millennial. While I've got an advanced degree and a job in the tech industry, I'm usually happiest in my kitchen, garden, and home, or else on a crazy travel adventure. I hope you enjoy my recipes, home improvement tips, travel stories, musings, and more. You can also see what I'm up to in my professional life at Need to reach me? Shoot an email to whitney (dot) magnuson (at) gmail (dot) com.

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