CHAPTER 5: Booking the Dream


In the end, it all comes down to the free breakfasts.

But, let’s not get ahead of ourselves.

Flying first class on Asiana and Korean Air hardly satiated my appetite for aspirational first class travel experiences; to the contrary, it only left me more hungry. The experience is simply exceptional. There’s no way around it.

Over the years, the possibilities of extravagant awards turned into a bit of a game for me. The more I mastered each of the reward programs out there, and the more I followed the many resources published in the online community of points bloggers, the more obsessed I became with the whole venture. I had never really had a hobby before, nothing of this magnitude for sure, and there was something fantastically exciting about seeing what I could accomplish, mastering the newest tricks.

Achievement Unlocked: Hotel Status.” or “Level 14: To Europe and Back”.

The problem with any addiction is that the more you serve it, the less you are fulfilled with each experience.  After time, domestic first class upgrades felt like child’s play. Free travel for my spouse for a year on Southwest? That’s so 2014. Even first class on American from Dallas to Paris over the summer on an aging 777-200 felt like travel with the masses.

I needed something big. Something super big. I finally had a job that gave the flexibility and time off needed to make it happen, and the points accumulated to put my dreams to the test.

From the day that Etihad first announced the plans for the first class cabin on its A380, I was mesmerized. The hard product they developed is a step above and beyond anything the airline industry had ever before seen. A chair and a bed and a lounge and a shower. Oh my! I wanted to try it out myself, but how, and why? You don’t just fly to Abu Dhabi because. Do you?

For months I played around with itineraries, exercises in futility, mostly, because it was never going to actually happen. After its initial launch, the New York – Abu Dhabi route was rarely available except for days before the flight. My job was flexible, but not that flexible. There was a new route opening up between Abu Dhabi and Sydney which did have availability, and Danielle’s number one vacation interest was Sydney, but we’d still have to get to Abu Dhabi, and back home from Sydney, not to mention a month for all that travel, which we didn’t have. It didn’t add up.

The other big interest, high on my list, was Emirates. Another A380 with super first class service, this was high on my list but outside of what I thought was possible. The number one way to book award tickets on Emirates is (*was) with Alaska Airlines points. Starwood (SPG) points can transfer over to Alaska, but I didn’t have anywhere close to the 180,000 Alaska points necessary to make those bookings happen. Options for racking up the remaining Alaska points seemed daunting – it would involve a lot of churning – so I sat on the opportunity for a while, and did nothing.

I kept playing with options, testing out itineraries and destinations. For weeks, I toyed with the idea of making some of these bookings, but where would we fly to? Was it really worth it to try out these flights without an ultimate destination?

That’s where the Hyatt Diamond Status popped into the picture last year. Out of nowhere, last November, I had Diamond status, with all its perks, including, above all, free breakfasts.


It hit me. What if I connected my desire to fly the aforementioned airplanes and cabins with a desire to maximize my newly-minted status? Where was the most ridiculous, expensive, out of the way, hard to stay at Hyatt property in the world, I wondered, the one place that I would have to get to during my year of status?

The Maldives.

The Park Hyatt Maldives, located on Hadahaa Island, is located, more or less, here:

Really, the middle of nowhere.

The hotel – made up of only 56 guest rooms – is the entirety of the island. The island is sits a few miles from the equator, a half hour speed boat’s ride from the nearest airport, located on Kooddoo Island to the north east. Kooddoo is only accessible by small planes that fly an hour south from the Maldives’ capital Male, which is itself a small island, in the middle of the Indian Ocean, about 500 miles southwest of Sri Lanka.

The Maldives are one of the most remote places on Earth, and the Park Hyatt Maldives is at one of the most remote corners of that island nation.

Achievement Unlocked: Go Super Far Away

What better spot, I thought, then to maximize my new Diamond benefits? After all, breakfast is expensive at a resort like this! A week’s stay would mean more than $500 in breakfast charges. I had to go there now! I’d save money! And, who knew, maybe I’d score an upgrade to a suite with a pool too. Done.

So now I knew the destination – Park Hyatt Maldives – and I knew more or less how I wanted to get there – flying Etihad First Class and Emirates First Class, both only on A380s. Because of availability on the Etihad route, I would have to book the return flight on Etihad and the outgoing leg on Emirates. Now the question was how to lock this all in.

I started honing in on December 2016 as my target travel time, and spent hours upon hours strategizing to make it happen.

American Airlines allows you to book awards on Etihad, and I had a ton of American miles. So long as I could find availability, this piece would be no problem. This was early December 2015, though, and still a few weeks before the flight schedule for December of the following year would be released, so I had time to work out arrangements for everything else in the meantime.

I had about 60,000 Starwood miles to my name, earned through a combination of hotel stays and credit card sign up bonuses. This would not be anything close to the total I would need to book an Emirates first class ticket on Alaska.

So I started churning.

The Bank of America Alaska Airlines Visa Signature Card came with a 30,000 mile sign up bonus after one purchase, and a $100 statement credit after meeting the small minimum spending requirement of $1,000, easily offsetting the annual fee.

So I applied for the card. And I applied again. And again. And again.

In total, I applied three times for myself and once for Danielle within a month’s time, netting 120,000 total miles with easy spending requirements and no annual fees paid. Each application was approved. My credit score took no hit. Carefully managing credit applications (I have a big ‘ole spreadsheet) allows you to work miracles.

Soon enough, I had the Alaska miles I needed, so I transferred over Starwood miles to top off my and Danielle’s accounts. Starwood miles can be transferred to a huge amount of Airline programs. For every 20,000 miles you transfer, SPG kicks in a 5,000 mile bonus – a HUGE win. With sufficient miles racked up, I booked award tickets from New York to Male, Maldives, flying through Dubai on an A380 followed by a 777 on flight number two. I knew that Alaska Airline awards can be cancelled with no penalty, so took no risk in locking in the flights.

The next bit was trickier.

I wanted to have about 5 days on the ground in the Maldives, plus 2 during a layover in Dubai (if I had to fly through there, I might as well see it, and Alaska allows layovers on award tickets – huzzah!). So, the morning that award availability opened up for seven days after the Emirates ticket I’d already booked, I was awake during the wee hours of the morning to try to book flights on First Class Apartments on the Emirates A380 from Abu Dhabi to New York.

Nothing was available.

I searched and searched. Nothing for that day, nothing for the day before, or the day before that for an entire week, in fact. There was availability on the nonstop of Abu Dhabi to Los Angeles (which, let’s be honest, would be a much more direct routing), but what was the point? I didn’t need to go all the way to the Maldives to sit on a 777 for 16 hours. Sure, I’d have a suite, and amazing service. But I was either going to go big or go home. And a 777 wasn’t big enough.

Award tickets require “Guest First” availability, of which there was none.

I was despondent. My hopes had been set high, and it was no longer possible.

Oh well.

That night, I had trouble sleeping, and finally, around 4 AM, I gave up. I started trying to get some work done on my computer, and quickly ended up back on the Etihad website, looking at award availability again.

That’s when I found it!

If I added one more day to the hypothetical trip, the availability was there. I would need to fly business class – not first – from Male to Abu Dhabi, but that’s a quick 4 hour flight, and then I’d have full run of my apartment (and the Etihad First Class lounge!).

Availability on American from JFK to home was very limited, and would mean needing to fly to LAX or having a 12 hour layover in JFK. I chose the former. But the JFK-LAX flight would be on American’s A321-Trasncon, with flat bed seats, and another review opportunity. Suddenly this became a tour-de-force!

At 5:02 that “cold” California winter morning, I ran to the bedroom and woke up Danielle. If I can get us to the Maldives for a week, and we’d fly on the most absurdly aspirational flights, and it would all be more or less free, will you come with me?

Pretty please!

She said yes, and I, like a child in Toys-R-Us on Christmas, went running. Now, given my extensive research and following of bulletin boards and blogs, I knew that there was one last potential snag. For the past few months, American Airlines booking agents in the US had been unable to see first class award availability on Etihad. American Airlines had not acknowledged that this was an issue, instead, agents were merely telling people that no availability existed. But American awards book into any “Guest First” seat available on Etihad, so if it showed on Etihad’s website, it should have been bookable via American.

That is the story, of how, one Sunday morning in December, I called Australia. I used Skype to call the American Airlines reservation desk in Sydney. The agent was able to see the availability on Etihad. 180,000 miles later, she booked the award for me, traveling from Male to Abu Dhabi to New York to LAX! Minutes later, the ticket showed up in our American accounts online – we were good to go!

Well, almost. I had to also book a stay at the hotel I was set on visiting. But that was easy. I had a ton of points, and booked the six nights at 25,000 Hyatt points each. Mission accomplished.

But ever in search of a better deal, I wanted more. Danielle applied for the Chase Hyatt card, which comes with a sign up bonus of two free nights at any Hyatt property (along with a ton of other fantastic perks). A few weeks later, I used that perk to book the final two nights of our stay, and saved myself 50,000 miles. Seeing as rooms at the Park Hyatt Maldives go for around $1,200 per night, that sign up bonus alone equates to $2,400 in value for us!

That was it. I had tickets booked from New York to Dubai, a layover of two days there, then an onward flight to the Maldives. We would stay at the Park Hyatt Maldives for a week, then fly back via Abu Dhabi.

Our routing.

The whole thing was free, and included in-flight showers, a resort nicer than anything I had ever imagined, and visits to countries I never thought I’d visit. And Danielle was coming with me!

It seemed too good to be true. But it wasn’t. We’re almost there. And it’s happening.

Total cost, in the end, was 180,000 Alaska Airlines miles (earned through credit card sign up bonuses and transfers of SPG points), 180,000 American miles, 100,000 Hyatt points and two free night certificates (earned through a credit card sign up bonus). Done. Done. Done.

For reference, the total value of this trip booked with cash is roughly $60,000, giving us a redemption value of more than 13 cents per point!


The timing could not have been more perfect. Only days after booking the Emirates award, Alaska Airlines gutted its partner award chart, doubling the cost of an Emirates first class ticket overnight, without notice. Months later, American Airlines also updated its award chart; the cost of our Etihad award has gone up to 115,000 miles instead of the prior 90,000 each way. This is still a worthwhile investment, but I’ll gladly save 25,000 miles any day of the week!

We booked it. We booked it at the perfect time. And now we’re going.

This is the story of what you can do collecting points.

Coming up on #pointedout, reviews of all the experiences I outlined above. Was it worth it? Am I crazy?