The whole idea of our honeymoon started with my obsession with points and miles, and learning that it was possible to fly Cathay Pacific in First Class all the way to Africa for only 70,000 Alaska Airlines Miles.

WARNING: Geeky Miles/Points post incoming. Read on only if you want to learn how to “Travel Hack”, and not for a trip report.
Back when SPG and Marriott were starting their integration, I purchased a few big chunks of Starpoints when they were discounted, converted them into Marriott points, and redeemed 270,000 of them for 120,000 Alaska Miles + a 7-night hotel stay (stay tuned for what I’m using that for!). I also went on a few mileage runs to earn the rest of the difference (including one routing from GIG-GRU-JNB-LHR for only ~$600 in business class that allowed me to experience JNB for the first time on a long layover, and also fly on the upper deck of an A380 for the first time!).

I found a date in August 2019 back in late 2018 that allowed me to book 1 seat each in First and Business from DFW-HKG, connecting in LAX with the first leg on Alaska in First Class, stopping over for ~30 hours so we could rest and get our dim sum fix on, and continuing from HKG -JNB in Business Class. Cathay doesn’t release more than 1 First Class seat in advance (naturally I gave Robert the available First seat and I took Business), and also doesn’t operate a plane with First Class to JNB. Cathay has historically released unsold first class seats in the weeks and days before departure, and with mid-August typically being a slower season for US-Asia travel, I thought the chances were good that another seat on the same flight (or two seats from a different US gateway) would be released so that we could fly together. Even still, I thought 30 hours x 2 people flying a mix of first/business class on one of the world’s best airlines, with a stopover in Hong Kong, was a phenomenal deal for 132,500 Alaska miles, which I spent a total of roughly ~$2200 for.

Eventually, I also discovered that I could book a trip on Singapore Airlines on the A350 from CPT-JNB-SIN-BKK for only 45,000 KrisFlyer miles. Singapore KrisFlyer miles are extremely easy to accrue, since they transfer from all US based credit card rewards programs (Chase, AMEX, and Citi). I thought this was another phenomenal deal for 15 hours in the sky in Business Class on one of the world’s most legendary airlines. I built in a long layover in SIN to explore the renowned airport and perhaps hop into the city to try some of the street food. Later, I found out that our flight from SIN-BKK got swapped to the new Boeing 787-10 Dreamliner, which means we get to fly in flat beds even on the short regional flight, and I get to check a brand new plane type off of my #avgeek list. Score!

In mid-2019, Chase announced the end of their partnership with Korean Air. The Korean Air Skypass program charged only 80,000 miles to travel from North Asia (anything from Hong Kong northwards) to North America in First Class, and includes a free stopover in Seoul. I speculatively transferred over 160,000 Chase points before the partnership ended in anticipation of utilizing this sweet spot. KAL always releases 2 seats for award tickets in advance, and after wiffle-waffling between flying on the A380 or the 747-8i, I settled on an itinerary from HKG-ICN (in First, operated by the 77W), stopping over for two days in Seoul, then taking ICN-ATL (in First, operated by the 747-8i) to take advantage of one last flight on the Queen of the Skies. I thought that was a great value for 160,000 Chase points, which is worth $2,400 in travel credits otherwise at 1.5 cents per point through the travel portal.

To fill in the remaining holes in the itinerary, I booked a flight from BKK-HKG on Cathay Pacific using British Airways Avios for only 15,000 Avios. Since there are plenty of flights between JNB-CPT available to travel standby on (a perk of Robert’s position with AA), and even confirmed last minute travel was cheap ( <$100 per person), I decided not to book a confirmed ticket as even booking through BA Avios would cost 15,000 miles and over $120 in taxes and fuel surcharges. Also in consideration was our lack of firm plans in CPT, so we had full flexibility to utilize standby travel. For that short flight, we instead paid roughly $44 for our standby tickets.

Lastly, to bring us back home, I found a ticket from ATL-DFW in First Class on AA, that connected on to one of the last scheduled MD-80 flights from DFW-IAH, for ~$180. Robert and I also both get 20% off all AA operated flights as a further perk of the job, so the price was $300 total, which I covered with $250 I had in random AA gift cards, along with $50 on my credit card. I would get to spend some time with friends in Houston, then could catch one of the numerous flights from Houston to Dallas to conclude our trip.
Cue Plot Twist!!
Two major events in 2019 would throw my meticulously planned trip into disarray. The first was Cathay Pacific’s infamous NYE Error Fare, in which they sold roundtrip tickets from Asia to the US in First Class for only $1100. It was an incredible deal for those that were able to book (I was at work, unfortunately), but it dried up almost all First Class availability from the US-HKG for revenue flights, much less Award Availability. At first, flights from LAX-HKG seemed relatively unaffected by the mistake fare tickets, but in Spring of 2019, Cathay Pacific pulled award availability 100% for ALL routes from US-HKG. It was a frustrating and seemingly punitive move against the “travel hacking” community, perhaps an effort to avoid further “cheapening” a flagship product that they already gave out virtually for free to thousands of people. I followed award availability like a hawk for months, and never saw a single seat open up for redemption in 2019, whether close in or far in advance.
That development in itself wasn’t enough to force me to change my plans. Even if we wouldn’t get to fly together, the ticket as is was still a great redemption, and I was only seated two rows behind Robert in Business Class, hardly slumming it ;). Plus, there were unconfirmed reports that flight attendants on Cathay were lenient with seat swaps and visits between cabins, so there was hope that we could at least share a glass of champagne together. And Robert would still be able to “guest” me into the exceptional First Class lounges in LAX and HKG.

The events that changed my mind, however, were the unfortunate developments in Hong Kong. The demonstrations near where we were planning to stay meant our relaxing, dim-sum fueled layover would be in a tense, potentially dangerous atmosphere. The disruption to airport operations, including two days of cancelled flights and countless other flights delayed, along with the dramatic ouster of several Cathay Pacific executives meant that there was a significant chance that our flight to JNB might be affected. Wanting to make sure our honeymoon got off to a good start, and with a nonrefundable safari lodge booking waiting for us in JNB, routing away from Hong Kong (at least on the outbound) was a no-brainer, even if it meant we would lose our coveted First/Business Class award redemptions.
Fortunately, the stellar customer service staff at Alaska (who we booked through originally) granted me a waiver, allowing me to cancel the tickets with a full refund without fees as soon as I found alternative flights. I eventually settled on Lufthansa First Class, as they offer the most luxurious and special product to JNB that is relatively easy to obtain using Points and Miles. LH First Class is legendary among the frequent flyer community, and combined with the impossibly extravagant First Class Terminal experience in Frankfurt, I’d been dreaming of trying it ever since I took my first exceptional flight on LH in Business. I considered Emirates First Class as well, but that would have cost me about 200,000 points + $1000 in surcharges to book….each!

I quickly started stalking the award availability trends on Lufthansa from FRA-JNB and was able to secure a pair of seats on the 747-8i (should make an interesting head to head with the Korean Air 747!). I booked one with 87,500 Aeroplan miles (I had ~17,000 left over in the account and transferred the remaining 70K from AMEX) and the other with 80,500 Singapore Krisflyer miles (I had ~1000 left over from a previous redemption and transferred 80K over from Chase) with ~$400 in taxes/fees per person, yielding a total “cost” of roughly ~$3200. AA flights from DFW-Europe were wide open when we needed to travel, so we hopped the pond for free and even secured a pair of premium seats. While this redemption wasn’t as **incredible** of a value as the Cathay redemption through Alaska was, it was still very good, allowing me to check off a bucket list item, travel in style, while minimizing any out of pocket expense.
People tell me all the time how rich they thing I must be to afford all this travel. While this trip certainly wasn’t cheap by any means, and exhausted a big chunk of my miles and points balance, it wasn’t nearly as pricey as if I had booked the trip with cash. It’s certainly worthwhile for a special occasion, in my opinion, and easily attainable even for somebody on a decidedly average service industry salary.
TOTAL COST: 160,000 Korean Air SkyPass Miles, 87,500 Aeroplan points, 170,000 KrisFlyer miles, 30,000 British Airways Avios, plus approx $1200.
If you’re made it till the end here, please let me know if you have any questions about how we booked this incredible trip! I may launch a travel hacking/booking service in the future, but right now the advice is free :). Which airline/plane/product are you most excited to see us review?