Happy New Year!  I hope 2023 is treating everyone well so far.  December ended up being a CRAZY month for me, involving not one but two Virgin Voyages cruises and then a sudden trip to South Africa for a New Year’s Eve double wedding at a winery estate built in the 1600s!

Many of my readers follow my Instagram account, where they saw plenty of stories about my flights down to South Africa and back in what is widely acknowledged as the best Business Class in the sky: Qatar Airways QSuites.  People rightly assumed that I used miles for the flights, since I’m not wealthy and wouldn’t randomly spend $7000 at the last minute to fly to a wedding.

The QSuites Review is coming, with 50+ pictures from my 50 hours in the air over the past week, but everyone has had the same question:

How did you find the space and how did you book it?!

 

Here’s the part nobody tells you about travel hacking

There’s a new generation of travel hackers on Instagram and TikTok doing some great work teaching people the ins and outs of travel hacking.  

I’ve been around the block a few times and I think there are “generations” of travel hacking content creators:

• The FlyerTalk generation (TPG, Gary Leff, Ben Schlappig, etc.)
• The BoardingArea generation (many of my BoardingArea blogging colleagues who were inspired by the FT generation)
• The Facebook generation (mainly the Award Travel 101 Facebook group but there are many others)
• The New Social generation (Instagram, TikTok, and what’s left of Clubhouse)

It really doesn’t matter which generation people are from, most travel hacking content creators tend to focus way more on earning points than redeeming them.  This is understandable, because earning points is often way more fun than trying to get the most value out of them.

Getting the most value for your points and miles takes time, often while you’re on vacation.

 

Here’s the timeline of how I booked my trip

My friends were getting married in a double wedding in South Africa on New Year’s Eve (I know both couples from doing life here in Dallas, Texas).  They invited me to the wedding but I never thought I’d be able to make it because New Year’s Eve falls right in the middle of South African summer and, therefore, right in the heart of the peak travel season there.  Still, they were getting married in Stellenbosch, the famous wine region just outside of Cape Town, so I was bummed that I couldn’t go.

Tuesday, December 27th

It was Tuesday morning and a South African friend of mine and her boyfriend were about to leave for Cape Town for the wedding and she said “you should book a flight and still come!”  I felt bad because there was no way I would be able to find a good award ticket, I thought.

At about 11am, I logged on to AA.com.  I searched award flights from DFW to CPT.

…and there was space on that night’s flight to Doha and onward to CPT on Qatar QSuites, leaving in roughly 7 hours.

…for 75k miles.

I did like three double-takes to make sure I was reading everything correctly.  I was.  I hurriedly put the one-way trip to South Africa on hold (it’s a general best practice to book one-way flights instead of round trips when using your points/miles, by the way) while I looked for a return flight.  I couldn’t really find a return flight before like January 20th using my American miles.  I knew that South Africa might ask for proof of onward travel, so I needed to have something booked to show I planned on leaving the country.  I booked a random United Economy award ticket for the end of January, with the full intention of finding something better and booking it while I was on my trip.

I booked the trip, booked a car rental and guesthouse near the wedding venue through the 1st of January, ran home to pack, and went out to DFW to begin my journey!

Total miles spent so far: 75k AAdvantage miles, 40k United miles, roughly $100 in taxes/fees
Money spent so far: Roughly $100 in taxes/fees, $300 on guesthouse, $110 for rental car
Time spent so far: about 45 minutes

Wednesday, December 28th

Whilst on my flights to South Africa (and the very long layover at the Al Mourjan lounge at DOH), I would occasionally check for award space to open up for the first week of January.  Nothing so far.  I briefly saw the award space I wanted for the return and called AA when I was having trouble booking it, the AA reservation agent had the exact same issues so at least it wasn’t me.

Total miles spent so far: 75k AAdvantage miles, 40k United miles
Money spent so far: Roughly $100 in taxes/fees, $300 on guesthouse, $110 for rental car
Time spent so far: about 2 hours

Thursday, December 29th

Landed in Cape Town and immediately smiled, and that smile never really left my face until I left.  Cape Town is one of the great cities in the world, and the Stellenbosch region is absurdly beautiful.  I acclimatized to driving on the left side of the road, made my way to my guesthouse, took an accidental nap, and casually checked for flights every now and then.  Still nothing.  No big deal, yet, as I can work remotely if I need to.  A friend who works for an airline and LOVES Cape Town ended up finding non-rev space and was on her way down to meet me and join for the festivities.

Total miles spent so far: 75k AAdvantage miles, 40k United miles
Money spent so far: Roughly $100 in taxes/fees, $300 on guesthouse, $110 for rental car
Time spent so far: about 3 hours

Friday, December 30th

Drove down to Simon’s Town to see the penguins and other assorted Cape Townery.  My friend was casually checking flight loads for non-rev space as I looked for award space back to Dallas.  Neither of us were finding much of anything.  She needed to be back home by January 3 so I went ahead and zoned in on searching for flights departing January 1 or 2.  I wasn’t finding anything using American miles so I looked at United.  Yeah, nah.  United wanted roughly 180k miles for a one-way ticket in coach.  Not a chance.  I wasn’t worried yet, and just increased my cadence of searching in case some space opened up (I would just pull up American’s app while we were out and about, it took about 10 seconds to run a search).

Total miles spent so far: 75k AAdvantage miles, 40k United miles
Money spent so far: Roughly $100 in taxes/fees, $300 on guesthouse, $110 for rental car
Time spent so far: about 4 hours (including time talking about options)

Saturday, December 31st

Wedding day!  The wedding was in the evening so we had plenty of time for a hike in the morning.  We also had plenty of time to search for flights in earnest.  We were both starting to get a bit nervous.  My schedule was more flexible than my friend’s but it would be really good for me to be back by January 5th and I just wasn’t finding anything back to Dallas.

I reverted to another best practice that I like to follow (“at least get to another airport where there’s a chance for better availability”) and began searching flights just from Cape Town to Doha, instead of Cape Town to DFW.  BOOM.  Found CPT to DOH on Qatar in Business Class for 55k miles on January 1st!  I booked it immediately.

Total miles spent so far: 130k AAdvantage miles, 40k United miles
Money spent so far: Roughly $100 in taxes/fees, $300 on guesthouse, $110 for rental car
Time spent so far: about 5 hours

Ok and then I began searching for how I could get home from Doha.  Originating in Doha opened some options for me, since American flies DOH-JFK, but American wanted 110k miles to fly DOH-JFK…in coach.  No thanks.  I looked up the US airports that Qatar serves from DOH (BOS, JFK, PHL, MIA, ORD, DFW, LAX, SFO, SEA) and began searching DOH-[those airports].  I knew that if I could find award space back to the US on one of the Qatar flights I could have the previous award re-priced as if it was one award.  But I couldn’t find ANYTHING.

Ugh.

I started looking at paying cash for the nonstop from Doha to DFW.  In coach.  I had the business ticket to Doha but didn’t want to enter Qatar, so I needed an onward ticket.  I had previously looked at one-way flights from Doha to DFW and they were like $2000!  I searched that day and it was “only” $953, so I just bit the bullet and bought it.  My “free” trip just got much more expensive and that was going to be a LONG flight in coach back to Dallas.  I went ahead and canceled my United trip so those miles could be reinstated into my account.

Total miles spent so far: 130k AAdvantage miles + 40k United miles
Money spent so far: Roughly $100 in taxes/fees, $300 on guesthouse, $110 for rental car, $953 one-way DOH-DFW
Time spent so far: about 8 hours

It was time for the wedding!

Sunday, January 1st

The weddings were fantastic and it was a great New Year’s party with some of the most fun and friendly people I’ve ever met.  We had such a great time.  I woke up the next morning pretty early, having not really adjusted to jet lag yet.  I couldn’t go back to sleep, so I just decided to search all the Doha-US flights again for awards.

WAIT.  THERE’S BUSINESS CLASS SPACE FROM DOHA TO MIAMI.

As a reminder: I had a 55k business class award ticket from CPT to DOH booked and a $953 cash fare from DOH to DFW.  The flight from DOH-MIA was pricing out at 70k miles, but I knew that American would likely reprice everything into a single 75k business class award CPT-DOH-MIA (in accordance with their oneworld partner award chart), but I needed to get American on the phone, and fast (my flight to Doha left in five hours).  It was 8:10am in Cape Town when I called American’s Executive Platinum line back in the States.  The reservation agent who answered was as chipper as could be and wished me a Happy New Year, and I realized it was just after midnight on New Year’s Day for her.  I needed an experienced agent to do some of what I needed to happen, so my fingers were crossed that she was the one.  She was AWESOME.  She knew what needed to happen and in what order.  I canceled my cash ticket DOH-DFW and she saw the award I had on hold.  She was able to combine the tickets into one award but, since the first flight was leaving so soon, was worried that it might not get through ticketing in time.

My friend and I were hurriedly packing and getting into the car.  It took the American agent 48 minutes to work through everything with a supervisor, and they reached out to Qatar and got everything ticketed!…but only to Miami.  There was no availability onward to Dallas.  I told her that was fine with me and we made our way to Cape Town and began the long journey home.

I’m so glad I was able to make it all happen but it certainly took a TON of time.

Total miles spent so far: 150k AAdvantage miles + 40k United miles
Money spent so far: Roughly $180 in taxes/fees, $300 on guesthouse, $110 for rental car, $953 one-way DOH-DFW
Time spent so far: about 12 hours

Monday, January 2nd

I was on final approach to Miami after an absolutely wonderful!  But I don’t live in Miami, I live in Dallas.  I had spent an hour or two searching online during the DOH-MIA flight and, unsurprisingly, there were few options to get back to Dallas using miles, and cash fares were VERY expensive.  I was exhausted from the entirety of the trip and just wanted to get home.  The only reasonable award flight that would get me home involved a late-night flight from Miami to Orlando, spending the night at MCO, and an early flight back to Dallas the next day.  For 29k miles.  Uggggggghhhhhhh.

I went ahead and booked that award flight, since cash fares were like $2000 (not kidding) since the only seats left were in First Class.  Just after we touched down in Miami, I was searching for cash fares MIA-DFW hoping some coach seats would open up as standby passengers cleared onto earlier flights (as is pretty common), and suddenly I saw a one-way fare for $476 for a flight that would get me back to Dallas that night.  I snatched it up, not even caring that it was normally WAY more expensive than I would typically tolerate.  I was ready to get home.  

The final tally and my thoughts on how I did overall

Here was the final tally across the six different versions of my itinerary.

Total miles spent so far: 150k AAdvantage miles + 40k United miles + 29k AAdvantage miles MIA-MCO-DFW
Money spent so far: Roughly $180 in taxes/fees, $300 on guesthouse, $110 for rental car, $953 one-way DOH-DFW, $476 one-way MIA-DFW
Time spent so far: about 13 hours

Anyone who travels a lot with miles and points will tell you that situations like what I was going through are not really that uncommon.  You can have the most points in the world but it just doesn’t matter if the availability isn’t there.  You are subject to what pricing algorithms and supercomputers tell an airline to release.  I did really well on this trip and got incredible value for my miles, but man I paid for it in the time I spent making it happen.  And it wasn’t just the time I spent booking it either, if I was not checking for flight availability I was usually thinking about it, so it occupied a lot of headspace for me the entire trip.  Time is a currency as much as money and miles are, and any points/miles enthusiast needs to be aware of the time it takes to make some of these “free” trips happen.  

In a perfect world I would’ve planned this out much further in advance, but I don’t think I would’ve been able to find the South Africa-America award space no matter how far in advance I checked, since it was peak season.  No matter what, I was going to end up spending lots of hours checking flights while I was on vacation.

Getting to see my friends get married in Stellenbosch on New Year’s Eve, though, was worth every second, mile, and dollar it took to make it all happen!

 

Hope you enjoyed the play-by-play of how I booked this trip!  Leave questions in the comments below!