Prepping for last-minute travel? Huh? (Nick’s Flying by the Seat of our Points Journal)

When Greg floated the idea that we all write a post about how we’re preparing for Flying by the Seat of our Points, I thought he was nuts. Prepare? For a last-minute challenge where I don’t know where I’m going or where I’m coming from or what’s next? How in the world would I do that?

Don’t get me wrong, having a general knowledge of award charts and award programs will help. And there are award booking tools that we’ve covered extensively. But I kinda figured that my job here was to show up when and where I’m told and then use an award booking tool to tell me how I’m getting to where I need to go. What more could I possibly do to prepare?

But I have to admit, Greg made me nervous. He made it seem like it should be obvious what I ought to be doing to prepare. That made me re-think things a bit.

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!

The post Prepping for last-minute travel? Huh? (Nick’s Flying by the Seat of our Points Journal) appeared first on Frequent Miler. Frequent Miler may receive compensation from CHASE. American Express, Capital One, or other partners.