A quick LA turnaround turns into a lot of striking out (Nick’s Flying by the Seat of our Points Journal)

Stephen and Carrie shared that my international divergence destination is Morocco! I had to scramble to get out of LA as quickly as I could — and unfortunately, I haven’t had much luck in figuring out this puzzle. Will I make it on time for the 2pm Friday live stream on Youtube? I legitimately don’t know — and neither will you unless you tune in!

Our 2024 team challenge Flying by the Seat of our Points tested our last minute award booking skills with a series of last minute travel challenges assigned and judged by Stephen and Carrie. Over the span of a week, Greg, Nick, and Tim used their knowledge, points, elite standings, and even upgrade instruments to tackle each challenge with the best combination of frugality and luxury they could, all before the next assignments were given. Final Scores: Tim won this challenge by the seat of his points!

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Check out our contestant journals, recap videos, and more here. And follow us on Instagram, YouTube, and this blog to find out about our future challenges!

June 6, 2024

We got our international divergence assignments last night from Carrie and Stephen and I’m being sent to Morocco! I was immediately excited both by the country and the challenges I’ve been given. I’ve never been to Morocco and have long been curious. Here we go!

Unfortunately, my enthusiasm was not met by much along the lines of award availability. In fact, all three of us found it exceptionally difficult to look at awards from the west coast last night. That was partly influenced by it just being harder than travel from the east coast and partly by the fact that by the time we got our assignments, flights directly from the west coast to Europe were already gone for the day. Whereas there are many later evening departures on the east coast, the west coast departures appear to be timed for an afternoon departure.

That made things much more difficult through the lens of our challenge. If we found a flight departing the west coast, it most likely wouldn’t be departing until this afternoon and arriving late morning (as late as noon in some cases) in Europe. That would make it tight for any of us who has to connect (which was certainly going to be the case no matter what for Greg and I and most likely for Tim also).

I quickly adapted to looking for awards from the east coast, but I couldn’t find anything that really worked there, either. I was still pretty confident that something would open up, but I didn’t know where that would happen. Around 9pm Pacific time, I realized that I had to get out of LA. If I stayed, given the arrival times of west coast flights to Europe, I’d have a very hard time connecting to Morocco and being there in time for our check in. Keep in mind that Morocco is one hour closer to Eastern time than Greg and Tim will be, so I’d theoretically need to be checked in at a hotel by the 7pm start.

I found that there was an American Airlines business class award available from Los Angeles to Chicago that was departing at 10:59pm and arriving in Chicago at 5am. It would only give me 4 hours in the air, and not in a flat bed seat, but I figured that I had to get some sleep. And by arriving in Chicago at 5am, I’d be positioning myself to be within about a 2 hour flight of so many airports, both east and west of Chicago, that surely I would find something available to Morocco.

A break came in the car on the way to the airport: Suddenly I found that the New York JFK to Casablanca Royal Air Maroc flight was available, but only as a married segment. Tim and I had discussed the fact that we had both seen the JFK-CMN flight widely available in the days before the challenge (I guess we both had our eye on it!), but when we signed off from zoom, we didn’t see any availability. On the way to the airport, I found it available from New York JFK to Casablanca (CMN) and onward to Marrakesh (RAK). That seemed perfect!

Perfect….except for the fact that I was in Los Angeles and on my way to fly to Chicago. Still, with my Chicago flight landing at 5am local time and the JFK to Morocco flight departing at 11:50am, I figured I had plenty of time to get to New York JFK.

As it turned out, I was wrong, The only flights from Chicago that would give me a prayer of making it were a Delta and a United flight, both scheduled to take off at 6am (which means they’d be boarding from a different terminal just 30 minutes after I was due to land) and both scheduled to arrive at New York LaGuardia at 9am. That would mean I’d have to get out of the airport and catch a Lyft to JFK and contend with morning rush hour traffic to be sure I arrived at the airport before they cut off international check-in (presumably at 10:20am). It was possible, but not a slam dunk by any means.

As fate would have it, I arrived at Chicago and knew exactly where to go for the bus that connects terminals airside at O’Hare airport…..only to find out when I got there (at the far end of the terminal at which I arrived) that the shuttle bus only runs between 11:30am and 9:30pm. After that time, you need to exit security, use the airport transit to switch terminals, and get through security again. At that point, it was about quarter after 5 and there was no way I was going to make it the length of that terminal, take a train to another terminal, clear security, and get to the gate in time. I was sunk.

So I had to cancel that itinerary. That was a shame since New York to Casablanca to Marrakesh was just 45,000 Alaska Airlines miles and about $240 or 57,500 American Airlines miles and $5.60. I had chosen to use the extra 12.5K AA miles to save the $200+ in fees, but it was no use. I had to cancel it.

I hustled up and looked for other awards. It looked like there was tons of Swissair space from several airports. The night before, Chicago to Zurich had shown 3 seats available. Tim had tried to book that only to have it error out. He called and they couldn’t see it. The space turned out to be phantom. A later search at United and click through attempt to see if I could get to a checkout page (after the same flight showed five available seats the next day) proved that it was phantom. Tim tried a bunch of it to. That was frustrating since it showed up via some of the award search tools but it wasn’t actually bookable.

I would have loved to have used my Air France KLM Flying Blue miles, but the only airports where I found reasonably priced Flying Blue awards (less than ~150K one way) were in Canada. All of those flights arrived a little too late in Europe — the available connections to Morocco from those all landed in Morocco after the 7pm check-in time. I had already used 25K Alaska miles getting to Chicago — I didn’t want to use another 150K+ to get to Morocco.

I went through similar stuff with other dribs and drabs I found — there just wasn’t something that didn’t cost an arm and a leg that did get in on time. I take that back: there was one flight from Dallas to Madrid to Casablanca and Alaska had availability for just 7,500 miles for the Chicago to Dallas leg, but that flight would leave in just 1 hour. I scrambled to book the Dallas-to-Morocco portion — and then it became too late to book the leg from Chicago to Dallas (it was no longer bookable online at all, whether with miles or money). I ran into trouble with miles from my cancelled Royal Air Maroc itinerary not automatically redepositing — and then we used my wife’s miles to book that Dallas-Madrid-Casablanca itinerary that I couldn’t make and it errored on the payment page and just put the itinerary on hold. She wasn’t available to call and I couldn’t get to Dallas in time.

Eventually, I settled on a far-from-ideal option also departing from Dallas and going through Paris. The way I put it together, which I’ll share later, left me with a tight separate ticket booking that I thought was possible and not terribly reckless, but also optimistic.

And in fact, I am finishing this up aboard the now-hour-delayed flight from Dallas to Paris pretty sure that this isn’t all going to work out according to plan. Of course, while I sat at the gate waiting to board, I worked out a backup plan.

Will I make it to Morocco in time for the 2pm Eastern time Friday check-in? I really don’t know. I hope so. Will I have used more miles than everyone else? Again, I don’t yet know. You and I will both have to hope to tune in at 2pm Eastern time tomorrow to find out!

Previous Journal entries

June 4, 2024

Installing the Points Path browser extension mere hours before Carrie and Stephen revealed the first destination turned out to be a great decision. I was able to look quickly at Google Flights and sort by arrival time to see which of the major US programs had availability and flights that arrived with good timing. Since the major US programs don’t offer much award space to partners, this proved to be a great way to get a lay of the land from the jump.

Sure enough, I was stymied by United’s newfound stinginess. I initially figured it would be easy enough to book a United economy class award via Turkish Miles & Smiles, but I found almost no United award availability that could be booked via partners from my home airport of Albany or from the New York and Boston area airports. I certainly wasn’t going to pay United 36,000 miles for an economy class award to LA!

With Southwest prices being high close-in to travel and Delta prices being Delta prices, that left me to pretty quickly zero in on American Airlines AAdvantage.

When we laid out plans for the challenge, and even when Stephen and Carrie began explaining our initial destination last night (on our live stream, they revealed that the three of us will meet in Los Angeles tomorrow), I figured this part of the challenge would be incredibly easy for me. Living in the Northeast, I have my choice of airports. Yes, Albany (ALB) is my closest. But within a 4-hour drive, I’ve also got White Plains (HPN), Syracuse (SYR), Hartford-Bradley (BDL), Newark (EWR), New York-JFK, New York-LGA, Long Island-Islip (ISP), Binghamton (BGM), and Ithaca (ITH). I walked into this like a major leaguer at a tee ball game.

However, Stephen and Carrie did a remarkable job setting the constraints on this part of the challenge: the rule was that contestants should not arrive before 3pm local (Pacific) time. That meant arriving in a pretty tight window since our live stream is at 9pm Eastern (6pm in Los Angeles). We would essentially need to arrive after 3pm but probably on something scheduled to land before 5pm to allow for enough time for us to get out of the airport, through LA traffic, and to our hotel in time for the 6pm live stream.

Recognizing that it might be tough for me since I’m traveling from the east cost, the judges built in a rule-breaker: if a contestant arrives on a flight scheduled to land before 3pm, they must not leave the airport before 3:30pm. That was meant to prevent Tim from flying in at 8am to beat us to the hotel. If you missed the live stream, we only have two hotel rooms for the 3 of us, so the first person to arrive gets their own room whereas the other two have to compete to keep each other awake with their snoring.

That all sounded well and good until I realized that in order to arrive at Los Angeles around 3pm, my only options from the east coast, no matter which airport I tried, would be leaving early in the morning (like between 5am and 9am). That turned out to be hugely problematic. I was really excited when I found lie-flat business class availability from Boston to Los Angeles for 35.5K American Airlines miles or 35K Alaska Mileage Plan miles through an award search tool. A little further inspection of my own revealed that the same lie-flat seats were available via Cathay Pacific Asia Miles for 33K miles. That sounded great….except that of the few options available, the latest departure was about 9:30am. That would put me in Los Angeles well ahead of schedule, meaning I’d take the 3:30pm penalty.

But that didn’t end up being the biggest part of the problem. If I were departing Boston at 9:30am, that would mean I’d need to arrive at Boston by 7:30am. Given that Boston is about 4 hours away, that would mean leaving my house around 3:30am to drive for four hours. That didn’t sound good. Even if I wanted to drive for four hours at 3:30am, would I pay for a week’s worth of parking at Boston airport? Then I’d have to fly back into Boston (and drive 4hrs after a week of exhausting travel). And I’d be on the hook for parking. I could alternatively do a one-way car rental, but then Carrie and Stephen would be figuring that expense into the judging. Arriving in Boston the night before the flight (tonight) sounded better, but then I’d have had the cost of a hotel on top of the cost of parking at Boston for a week or a one-way rental. Amtrak sounded like it might be a good fit, but we had a commitment at home today from 3pm-4pm, so I couldn’t make a train that would get to Boston tonight and I’d still be on the hook for a hotel even if I could have.

I essentially ran into that same problem with every airport. I was looking at ~6am flights out of most of them and the cost of either a hotel and parking or a hotel and rental car, which would drive up my cost considerably. Parking at Albany airport is pretty reasonable, so I’m a bit spoiled by that.

After hours of looking at other options, I realized that departing Albany, which is about an hour away from home for me, was the only realistic option.

Once I resigned myself to flying out of Albany, I thought that if I could get to some other west coast airport, I could stay there and time out a perfect arrival at LAX around 3pm (which is what I imagine Greg and Tim are trying to do). For example, I found that there was a United flight that was scheduled to fly from San Francisco (SFO) to LAX and land at exactly 3pm. Unfortunately, I couldn’t find a great option to get to San Francisco using my American Airlines miles.

I looked at every other major airport in California as well. I found a one-stop itinerary from Albany to Santa Barbara that would land around 11:40am and it only cost 9,000 miles one-way. That seemed like a really cheap way to get to the west coast. Then I could get a bus for $65 that would be scheduled to arrive at LAX at 3:15pm. But it’s a long drive from Santa Barbara and LA traffic is notoriously slow. That made me a little nervous. And it didn’t seem terribly comfortable. One-way car rentals were pricey enough to erase the savings of not flying into LAX.

And so, in the end, I kept coming back to an option I found very quickly at the beginning: a two-stop itinerary from Albany to Los Angeles that is scheduled to arrive just after 3pm. I booked an economy class award for 13,000 American Airlines miles and $5.60. I picked the specific itinerary I did in part because of the available seats: thanks to my American Airlines elite status, I was able to select exit row seats for free. I got an aisle exit row seat on each flight. Then I also noticed that the longest flight in the itinerary (Philadelphia to Phoenix) is scheduled to have snacks and drinks for purchase. My AAdvantage Aviator Silver card offers up to $25 per day in statement credits for in-flight food and beverage purchases, so I’d eat and drink for free. It also offers up to $50 in Wi-Fi fee reimbursements (in case my flight doesn’t have free T-Mobile internet). With a bunch of extra legroom, free food and drinks, and free Wi-Fi, I decided that this felt like a pretty close approximation of the domestic first class experience but at an economy class price!

But that wasn’t all. There were also a lot of open seats in first class. I knew that there was a chance that I might score a free upgrade. I ended up booking this itinerary last night. Early this morning, more than 24 hours before my flight, I got the email saying that my complimentary upgrade cleared for the longest leg, Philadelphia to Phoenix. For those curious, I had looked up the cost of a cash upgrade for just that segment shortly before that and the cash cost to upgrade that segment was $702. I scored that upgrade for free thanks to the American Airlines elite status that I’ve earned through shopping portal shenanigans!

At the end of the day, I’ve got a mixed-cabin itinerary with my longest leg up front for just 13,000 miles and $5.60 thanks to my easy American Airlines elite status. And I’m not even sure we’re done on that front — there are several seats still available up front on my flight into LAX. I won’t hold my breath, but I think there is a chance that I could end up in domestic first for 2/3 segments. We’ll see!

My flight is scheduled to land at LAX at 3:18pm. If it lands directly on schedule, I’m concerned. If Greg or Tim decided to arrive early, one of them could be waiting at the door ready to walk out at 3:30pm, and I’m not confident that I’ll be deplaned and at the door ahead of them. However, looking over Flight Aware, it appears that this flight is about 15 minutes early around half the time. If that happens, I feel like I could make a run for it. On the other hand, the same flight arrived about 45 minutes late one day within the last week. That would stink!

At the end of the day, I was a little disappointed that I couldn’t make a lie-flat transcontinental flight work. Leaving out of any airport other than Albany just didn’t make sense. That was a shame because a reader shared a hot route tip that I couldn’t use.

Still, if I use just 13,000 miles, fly the long segment in business, arrive right at 3pm, and still lose this segment of the challenge, it will mean that Tim and Greg must have really gone all-out.

Regarding food: Our travel challenge in Los Angeles is to find some food that represents where we think we’re headed next. The contestant who comes geographically closest gets bonus points. I narrowed down to three pretty specific guesses today and I consulted with a friend who lives in LA. Our friend is not a culinary concierge, but both my wife and I immediately thought of her when Carrie and Stephen outlined this part of the challenge. She really came through (I think) with some good recommendations. I’m going to hold off on sharing my guess until the live stream, but I feel pretty good about the cuisine that I’m settled upon for dinner tomorrow night — and what I expect may also be lunch the following day :-).

June 3, 2024 (Hours before we begin!)

Over the past 48 hours, it’s started to feel very real that I’ll be taking off in a couple of days with no idea where I’m going. I ended up doing quite a few last-minute things to prep over the past 24 hours:

• I finally installed the Points Path browser extension. Frankly, it was stupid that I hadn’t done that previously. I realized that when we get our Domestic Convergence destination announced, this extension will give me a really quick way to immediately search availability via the major US programs so I can book something in seconds and then move on to improving it thanks to free changes and cancellations from the major US-based programs. Hopefully, that will give me a small leg up.
• I had a small fib in my points balances below. I had listed about 280K Virgin Atlantic Flying Club points, but that was a half-truth. Those points were tied up in a booking I’d made for later this summer to fly from Johannesburg to New York. I’ve long since changed and plans and won’t be going to South Africa this year, so I’d been meaning to call and cancel that booking — and as such I had counted the points in my balances. I’d been too lazy to actually call and cancel, but I realized that much yesterday and thought that I’d love to be able to use these existing miles instead of transferring more points if I can, so I finally called to cancel. A nice surprise: I expected a $50 cancellation fee per passenger, but it turned out to be 30 Great British Pounds per passenger. That worked out to just over $38 per passenger, which meant that cancellation cost me almost $50 less than expected! The points were immediately redeposited, so they are officially available as listed below.
• I decided to go rogue and try to add a wildcard piece of equipment to my trip. On our Party of 5 challenge last year, Greg brought an Insta360 X3 camera. We got some awesome footage of ANA First Class, rafting and helicoptering around Igauzu Falls, and a lot more. The camera’s proprietary software ended up being something of a bear to use and as a result, we lost some steam with its use over time. Still, I couldn’t get it out of my mind. Yesterday, I bought an Insta360 X4 (our Amazon affiliate link) — the 2024 version — with the intention to try it out on this trip and see if the software has improved at all and whether I can get into the swing of taking footage and editing it on the fly. I am thoroughly unconvinced that this will be useful, but I am simultaneously excited to try it out and see how it goes because I could see this being a great way to capture some of our family adventures as well if I can master it. We’ll see!
• I’m leaning into loving Seats.Aero. I love messages like this one, that tells me that another program can book the same flight for fewer miles!
• I’m starting to get packed up and I did in fact buy another wool shirt for this trip (to have 3 in total), but I didn’t buy from Wool & Prince. Rather, I bought from Amazon instead to save a few bucks and see how it goes. I’ve also decided not to bring my Rimowa carry-on but rather my Muji carry-on for this trip. I’ve previously written a post comparing them (which is pretty ridiculous when you consider the fact that the Rimowa literally costs 10 times the price of a Muji!). For this trip, I decided that I just value the ability to zip away wet / dirty clothes to keep them separate too much to bring the Rimowa. I also miss the wheel-locking feature every time I’m without my Muji bags. Muji for the win!
• I’ve got a small bit of panicked searching. I’ve misplaced a spare wallet at home that has my Venture X card in it. I’ll be really burned if we end up getting sent to or through Dallas-Fort Worth airport or Washington Dulles and I don’t have access to the Capital One lounge! The hunt is on to find it — and I’m under the clock!

Otherwise, I’m mostly ready for anything. I often say that as long as I have my ID and a couple of credit cards, I’m good to go. Hopefully that holds up!

May 24th 2024 (1.5 weeks before the challenge)

With a week and a half to go before we find out where we need to be domestically, you might imagine that I’m at home poring over award charts, familiarizing myself with availability patterns, and trying to figure out how to pack for a trip where I have no clue what to expect. That would be a safe bet, but scared money wins no money: I’m typing this post on my way to fabulous Las Vegas for an epic status match run. That’s right, I’m throwing caution to the wind and puttin’ it all on red.

Who am I kidding? I’m in Las Vegas so my wife can enjoy the $150 Fine Hotels & Resorts and $100 Platinum status spa credits at Wynn (times two each), $300 in spa credits at Fontainebleau (both her $150 and mine). That’s because, for the 5th time in the last 5 or 6 years, I’m about to jet off around the world on a wild adventure while she maintains the home front. A trip to Las Vegas to let her enjoy copious spa credits made sense to butter her up before I sip champagne and chow down on fine food with good friends somewhere exotic. Oh, and we’re suckers for two more “free” Holland America cruises.

But I digress. What’s this about preparing?

What I know about preparing is the phrase my father held onto (and later imparted upon us) from the sign that hung above his college gymnastics team’s locker room door: The will to win is not nearly so important as the will to prepare to win.

I’d like to think that I’m willing to prepare…..but I don’t think I’m preparing the same way as Greg.

What to pack?

While Greg is greasing the wheels of his loyalty programs, my thoughts turn to an entirely different set of wheels: the ones on my carry-on bag. No, I’m not really worried about my bag’s wheels, but I am worried about what in the world is going to be in it?

I know that stands in stark contrast to Greg’s preparation post. If you read Greg’s post the other day, you would know that Greg has wanted to make sure that his accounts are linked and functioning and that transfers work from here to there and everywhere. Personally, I’ve rarely ever run into issues transferring points or miles to my own accounts. The times I have had an issue have almost invariably been when trying to make a small transfer followed by a larger transfer to the same program. I’ve long railed against the whole idea of a “test transfer” as I think it only increases one’s odds of having a problem. If you have a complicated name situation (like Greg’s hyphenated last name!), then I can see wanting to make sure everything is linked up properly. But for guys named Nick Reyes, I don’t think a test transfer makes sense.

And thus the only “greasing of the wheels” I’m doing in that realm is making sure that I have programs linked where applicable (not testing transfers) and making sure that, for my Amex cards, I have access to a file that contains the 3-digit codes from the backs of my cards as Amex often asks for that while making a transfer.

I’m not too worried about the points transfer side of things, but I am quite concerned with how I’m going to pack for a trip with no idea where I’m going or exactly how I’m going to get there. It probably goes without saying that I’ll travel carry-on-only. And while I’ve tried to do past challenges with only a large Tumi backpack, I’ve had to change to a newer (and unfortunately much smaller) Tumi backpack (I flew with it today and I am already regretting settling on the smaller size — I might end up selling it after this challenge to buy something bigger). I definitely can’t carry everything I’m going to need in my new backpack, so I’m going to be bringing a rolling carry-on for sure this time around. Hopefully I don’t end up getting dinged for carry-on fees with a budget carrier somewhere!

But having space to put things is only half the battle: what do I put in my bags? Shorts? Pants? Do I need a winter coat or a bathing suit — or both? What about footwear? I have comfortable shoes for walking around, but if I’m going to the beach I’d rather have sandals. And am I going to have any time for laundry along the way?

Shirts

To that last point, I’ve all but decided that I’m going to go for a full Merino wool strategy. I tried out a Merino wool shirt on our 3 Cards 3 Continents challenge and I was really pleasantly surprised that it lived up to the hype: Merino wool doesn’t seem to pick up any odor at all. Even better, Merino wool seems to dry very quickly. A couple of times, I’ve washed one of my wool shirts in a hotel room sink (using shampoo since the thing is made of animal hair!), rung it out as best I could (rolling it into a towel to squeeze out as much excess water as possible helps!), and then hung it up and it was dry by morning.

I think I’m going to pick up at least two more merino wool shirts — one with short sleeves and one with long sleeves since I have no idea where Carrie and Stephen will send us or what kind of weather to expect. I’m hoping that by bringing those two new shirts and one of my existing Merino wool shirts, I’ll be good to go for shirts. For those curious, I bought Wool & Prince Merino wool shirts before (that’s not any sort of affiliate link, just a link to their site). That’s the only brand I’ve tried, so I can’t speak to them compared to others.

To-do: Buy another shirt or two from Wool & Prince in the coming days.

Footwear

For footwear, I’m going with Allbirds. I finally gave them a shot (thanks to a sale and 22% back from Capital  One Shopping) long after their moment as the “hip” brand of travel footwear had seemingly passed and I’m in love with them. My merino wool pair is comfortable enough to walk around for hours and stylish enough to look good when I want to pull off a more business casualy look. Best of all, they don’t pick up any odor, even if I don’t wear socks.

If space allows, I’ll also put a pair of rubber sandals in my bag. A few years ago, I used a Saks $50 Platinum card credit to buy a pair like this only in solid black. I’ve worn them all summer long around the house and around town for the past summer or two and I’m starting to finally understand crocs (which never remotely appealed to me!).

Pants

I know that in most parts of the world, people wear pants even when it’s very hot. I’m cool with that, but at the same time if Carrie and Stephen send me somewhere where it’s 90 degrees in a shady breeze, I’d probably prefer some shorts. I’m currently leaning toward bringing one pair of regular pants and one pair of zip-off “convertible” pants where I can turn them into shorts by zipping off the legs (I have a pair like this one that I’ve had for probably 15 years and a second pair I bought in South Africa almost 10 years ago).

Warmth

I love a good hoodie.

I have had Baubax and Scottevest travel hoodies in the past. I really love the number of pockets in the Scottevest hoodie. And I love the feel and look of the Baubax hoodie (and that it maintains a far number of pockets). Unfortunately, my Scottevest hoodie has been worn to the point of falling apart and my last Baubax hoodie must have gotten lost in the shuffle at some point, though construction quality wasn’t as good on version 2.0 as the original Kickstarter one.

Last winter, I bought a regular hoodie — nothing “travel” related about it — from a Canadian company called Wanakome. I love it. It only has two regular side pockets, so it is totally unideal from a “carrying stuff” standpoint, but it’s warm, it’s comfortable, and I love the thick straps. That’ll be the hoodie that comes in my bag.

I’ve also got a fleece-lined windbreaker that is reasonably waterproof and warm. I’m hoping that between that, the hoodie, and a long-sleeved merino wool short, I’ll be totally covered if I end up somewhere cold. And if I end up only spending time in warmer climates, you certainly won’t hear me complain.

Hatwear

As a man of many hats, which one will I bring on this trip? I obviously have to bring my Flying by the Seat of my Points official merch “trucker hat”.

Beyond that, what hat will I bring?

I don’t yet know! I have an old sort of fedora-style hat that’s not in the best of shape but that is incredibly comfortable for travel as it is lightweight, extremely breathable, and with a wide enough brim to block out a lot of sunlight. It’s lost its shape a bit, so I’ll have to see if I can fix it up or if I need to find a replacement.

Eyewear

I’ve been ordering my eyeglasses online for at least 15 years (I’m no eye doctor – proceed at your own risk). I long ordered from a site called Goggles4u that was incredibly cheap. I also tried Zenni Optical once or twice.

Then, a couple of years ago, I discovered KITS.com. I am a huge fan. KITS makes their glasses in Vancouver, ships within a day or two, and prices are more than fair (they switched pricing models this year and now all of their in-house frames are $28 with prescription lenses!). Quality is higher than I’ve found with the other online sites from which I’ve ordered.

I just recently bought a new pair of glasses from KITS and I ordered them in both regular eyeglasses and polarized sunglasses and I love them. I’ll be bringing both pairs with me on the trip.

GoPro

Switching gears from clothing to equipment, I plan to bring my GoPro. I have a super old model at this point — I think we got it as a gift in 2015 — but it functions as good as new and I’ve always been happier than I expected to be with video quality. My model is terrible in low light, but it’s great for that fisheye lens sort of shot when taking a picture of a business class cabin, a hotel room, or getting video footage under water. I brought the GoPro on our 3 Cards 3 Continents trip (which is how I got videos of me ziplining and jumping into waterfalls in the Philippines!), but I didn’t bring this along on my last trip or two and I really regretted it. I’m definitely bringing it this time.

To-do: Find my spare batteries and external charger and make sure I have an empty memory card or two.

Waterproof bag

Years ago, my sister gave my wife and I small waterproof bags as a Christmas gift. I’ve used it tons of times to carry my wallet into the pool / ocean so that I didn’t have to worry much if our bag got stolen while we were in the water. I’ll be bringing this along since I’ll be alone on the trip and might want to swim or be able to keep some things dry while sightseeing.

Award search practice

Familiarizing myself with bells and whistles

In late April and early May, I was busy trying to put the finishing touches on a big summer family trip that will happen later this summer. I had to work to thread the needle in terms of finding availability for the four of us en route to multiple stops while also having time to get work done and get back home in time for school to start. And we have a family member flying separately to join us for part of the trip. That gave me some opportunities to pick up real-world use of some booking tools.

I’ve really come to love Seats.aero. While I’d read Greg’s previous posts about it, it really started to click as to why he loves it so much as I got used to using it more and more often. I’ve been using the search within 60 days to monitor availability via several key programs in order to give me an idea as to which routes and sweet spots are at least somewhat likely to be available for booking close-in. I’ve also had fun testing out the Live Search.

I’ve similarly gotten used to frequently using both Pointsyeah and AwardTool over my many award searches. Pointsyeah’s Daydream Explorer is fun and I can really appreciate the multi-point search aspect of AwardTool. I’m starting to feel far more confident using these tools.

One thing I’m trying not to do is become overly reliant on search tools. My high school math teacher’s favorite refrain was, “There’s a U in calcUlater” — in other words, the operator of the tool needs to know enough about how it works to recognize whether the results make sense. Applied to award searches, this means that I need to be able to recognize which programs aren’t being searched — and which ones might offer even better pricing for the awards that come across from a search tool. Being ready to get the best value will mean brushing up both on the programs I know well and some that I know far less intimately.

Award chart brush-ups

I’m reasonably familiar with common award chart sweet slots. I have a pretty firm handle on how much American Airlines charges for various region combinations. I have a reasonably good idea of what to expect from programs like Air Canada Aeroplan, Virgin Atlantic, and Air France / KLM Flying Blue. That’s not at all an extensive list — but my point is that there a quite a few that I already know quite well. I’ll still brush up a bit to make sure that I have current pricing relatively fresh in my mind, but I won’t need extensive study on many programs.

However, there are a few where I think I could use a more thorough or focused brush-up, as follows:

• Etihad Guest: I know that they used to have different charts for different partners and now they feature one main distance-based chart, but I need a review of which airlines they partner with and to have a look at distance bands and hub airports for its partners as I feel like there could be something here somewhere.
• Gol Smiles: There’s no easy way to get Gol Smiles, but I want to review Gol’s route map. Before Party of 5, I hadn’t realized that I could use American Airlines miles to book Gol flights. I want to know more about where I can go and how much it would cost, whether booked via American, Air France / KLM Flying Blue, Etihad — or something else
• Avianca LifeMiles. I am very familiar with LifeMiles and have written extensively about the program and pricing sweet spots. What do I want to do here? Dig through partners for value. I only realized last year that LifeMiles partners with AeroMexico and I only recently realized that they partner with Iberia. I want to search through for what other partnerships I may be missing — and which may have pricing anomalies I can work.
• Virgin Atlantic. I know this program as well as I feel like I need to, but I want to look at last-minute availability trends. I figure that I will very likely fly Southwest to our domestic meetup point, but I’d like to have a better handle on what my other options might be. I have no idea what last-minute Delta availability looks like via Virgin form my home airport.
• Emirates Skywards. I’ve dug through Emirates partner awards a bit before and found nothing exciting, but since we have about 200K Emirates miles that will expire in a couple of years if not used, I feel motivated to figure out how I can use these other than flying Emirates first or business class.

Plan for Maintaining Sanity

Unlike Greg, I’m not really concerned about maintaining my sanity at all (maybe that’s easy if there’s none to maintain?).

As Greg knows, I don’t need much sleep — I often function well on 4 or 5 hours per night for a week or two before needing a full night’s sleep. The one thing I’ve found is a key for me is listening to music. And I get sick of both headphones and earbuds from time to time, so I’ll be bringing both my Google Pixel Buds Pro and my Bose QuietComfort 45 over-ear headphones so I can switch it up.

True confession: Part of the reason I bought the Pixel Buds Pro a couple of months ago was for this trip. I had Pixel Buds Series A that I liked well enough, but I went for the Pixel buds Pro in part for the extensive listening to music that helps me stay focused when it’s time to get a task accomplished and partly for the live translation feature. I’m really betting on the ability of the earbuds to listen to a foreign language and translate to come in handy at some point during this challenge. We’ll see!

While not mandatory for this challenge, I’m going to set a goal: on at least one flight or on at least one night during the trip, I’m going to watch a full movie on my laptop. I switched back to an Asus Zenbook a few months ago in part because I just love the OLED screen on it. I’ve really been wanting to kick back and enjoy a movie on it and I just haven’t made the time. So while it’s not really related to the challenge and I don’t need it to maintain my sanity, I’m setting a goal to relax enough at some point to watch a 2-3 hour movie on my laptop, start to finish. We’ll see if I make it! Leave me your suggestions for a great movie to download in advance and watch! It doesn’t need to be travel-related (though it can be). For what it’s worth, I tend to enjoy drama, action, biopics, and sci-fi. If you recommend Lord of the Rings or Harry Potter, I will fail at this goal because there is no way I’ll keep my eyes peeled for long enough to see the whole thing….no matter how much sleep I’ve had.

Inventory

Believe it or not, the pandemic did not do this to me. For many years, almost all of my points were in transferable currencies. I was lucky when the pandemic hit that I didn’t have much of anything booked that needed to be cancelled. The fragmentation you see below has been largely self-inflicted thanks to trips we have cancelled to change to something “better”. As a result, I have some semi-orphaned piles of points that I would love to use, though I won’t allow myself to lose at the cost of up some orphaned miles.

I’ll note that Greg (and probably Tim, too) has me by a country mile when it comes to point balances. Don’t get me wrong, I’ve got plenty of points — I’m not feeling sheepish by any stretch. But in comparison, my balances are significantly lower in part because I’m typically using double the points of Greg or Tim in order to fly my family of four. No complaints here at all, but it means that I burn through points at a fairly rapid clip. I’m not worried — I’ve already got the major flights and hotels booked up for a major summer trip for my family — the balances you see below are all fair game for this challenge. And in fact, because I’m comfortable enough with where we’re at and the speed with which we’ve earned points, my wife and I recently went after several cash back bonuses — we’re halfway to earning a combined $2,950 in cash back welcome bonuses right now. I might invest some of that money to buy a few more points in a crucial program or two ahead of the challenge, but as of now my balances are as follows . . .

Transferable currencies

Chase Ultimate Rewards: 550K

Amex Membership Rewards: 600K

Capital One miles: 245K

Citi ThankYou points: 12,000

Airline miles

• American Airlines AAdvantage: 500K
  • Platinum / oneworld Sapphire status
• Air France / KLM Flying Blue: 299K
• Virgin Atlantic Flying Club: 280K
• Southwest Airlines Rapid Rewards: 190K
  • $1850 in travel funds
• Emirates Skywards miles: 204K
• Alaska Mileage Plan: 108K
• United MileagePlus: 2K
  • $2200 in TravelBank (and a relevant Mile Play offer)
• Air Canada Aeroplan: 8K
• ANA: 30K
• JetBlue TrueBlue: 18K
  • $40.20
• Delta SkyMiles: 28K

Hotel points

• Marriott: 525K
  • Gold status
  • 3 free night certs: One 25K, two 35Ks
  • ~$750 in gift cards from my grandfathered 1.4cpp Capital One redemption
• Hilton: 290K
  • Diamond status
  • 2 free night certificates
• Hyatt: 250K
  • Globalist status
  • 2 suite upgrade awards
  • Two Cat 1-4 certificates (currently attached to a standard-priced Cat 4 stay after challenge)
• Wyndham: 100K
  • Diamond status
• IHG: 95K
  • Platinum status
  • One 40K free night certificate (not-top-offable)
• Choice: 54K

Car rental

• Hertz: 2300 points

Other points

• US Bank Altitude Reserve: 40K points (I might use these for a car rental or to see if I can find something interesting in the travel portal)

Join Team Nick(Subscribe to this Post)

When the challenge begins, I’ll be updating this post regularly. This will be my daily journal where I’ll document my plans, successes, and failures as I go along. I’ll also welcome help. Once we find out where I need to get to, you may have ideas that you’d like to share with me. Perhaps you’ll know a particularly great sweet-spot award to get me there. Or maybe you’ll know a great hotel deal in the destination city. Or maybe you’ll have other advice for the destination city: how to get around, where to eat, etc. If you’re interested in helping me, then commenting at the bottom of this post is how to do it. Also, by subscribing to this post’s comments, you’ll get emailed whenever someone (including me) adds a comment.

Each of the contestants will have a post like this one where everyone is welcome to participate by making suggestions in the comments. You can pick a single team to join (Team Greg, Team Nick, or Team Tim) or, you can click back and forth and help us all. Either way, we’re eager to hear from you!

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