By now, most everyone who’s reading this post knows that we’re mere hours away from the beginning of the 2024 Frequent Miler Challenge, “Flying by the Seat of our Points.” The crux of the contest is that Nick, Greg and I have to do a multi-day trip that emphasizes both luxury and value, but that also has two main obstacles: 1) we won’t know any of the destinations until about 48 hours before we need to be there and 2) Carrie and Stephen will be giving us challenges along the way that we’ll have to complete with flair and panache if we want annual challenge glory to be ours.
Now, I can be fairly competitive and I do enjoy games. I won’t lie, my first impulse was to book a bunch of good-value, cancelable award tickets from my home airport of Seattle to every major North American airport so that I’d have something at a good price when the first destination is finally announced (which will happen tonight at 9pm Eastern, by the way). However, my better angels prevailed, primarily because it seemed contrary to the purpose of this whole endeavor.
After all, if it’s really meant to be a challenge that forces us to use our miles and wits for last-minute travel, pre-booking seems outside of the spirit (and the fun) of what we’re doing. If someone actually had to fly somewhere at the last minute, they wouldn’t have the luxury of having access to 20-ish pre-booked flights across the US on the exact date that they needed to travel. In fact, the more I thought about it, the more I felt like any advance preparation would be sort of like getting an unsportsmanlike head start.
So, instead of laying out how I’m preparing, I’m going to tell you why I’m NOT doing any preparation whatsoever in advance of tonight’s announcement, as well as talk through a couple of challenges that I envision encountering. For me, this will truly be “last minute travel.”
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June 3rd 2024 (challenge day one)
How I’m NOT preparing for Flying by the Seat of our Points
A couple of weeks ago, Greg wrote the following in the intro to his challenge prep post:
In a team meeting, I suggested that we each post about how we’re preparing for the challenge. Nick and Tim stared back at me blankly. How does one prepare for a challenge like this?
I’ll admit, he’s right on. My stare was about as blank as could be (but that’s normal). However, what I was actually thinking was “should we prepare for a challenge like this?” We already have one big leg up on anyone who would have to do a similar trip to what we’re attempting here: we know that it’s going to happen. Our schedules are cleared, our families know what’s up and we’re aware of the general timeframe that we’ll be travelling. Given that, I thought it would be fun to try to, as much as possible, maintain the same conditions that existed for me at the exact moment we decided to do this challenge.
So, in the hopefully true spirit of “last minute travel,” I’ve tried as best I could to not do anything out of the ordinary to prepare in advance. This includes:
- I’ve not transferred or earned any points or miles with the purpose of using them in the challenge. What I have, I have. What I’ve gained, I’ve gained through normal activity, without trying to change my earning patterns to accommodate the challenge. Those rewards programs that have extended transfer times will be out of reach for me.
- I haven’t read Carrie and Stephen’s post about how they’re going to score the challenge. There are two reasons for this: 1) I don’t want to allow myself time to strategize beforehand and 2) I don’t want the scoring rules to affect how I think about my primary goal: booking the most luxurious flights and hotels at the best value that make the most sense logistically based on our destinations. Anybody who watches tonight’s livestream will come in knowing more about how the gamemasters will be judging us than I will.
- I’ve not spent any time poring over award charts or program rules in order to prepare for short-in booking. What I knew when we decided to do the challenge is what I know today…and let’s be honest, given my age, I might even know a little less!
- I haven’t done any research on routes, schedules, weather or destinations.
- I haven’t practiced booking short term awards nor done any searches to see if/which programs are releasing close-in award space currently.
- I haven’t purchased any accessories or tools for use on the challenge, nor have I changed my subscriptions on any award tool services.
Now, those who’ve already read Nick and Greg’s posts about what they’re doing to prepare will notice that my approach is a little different. Will my dedication to observing both the letter and the spirit of the challenge rules give me any additional brownie points in the eyes of either the British or West Virginian judges (Stephen and Carrie)?
Probably not. They’re a tough crowd.
However, I hope that it will make all this business just a teensy bit more fun.
Things I hope will help me during Flying by the Seat of our Points
One advantage that Greg, Nick and I have with last minute bookings is that all of us travel a lot…and we book more flights and hotels with points than the average Jan or Joe. As a result, we all have practices that we’ve developed over the years that will hopefully help us wow the judges this week. Here’s a few of mine:
- Travel light, pack well: It normally takes me under ten minutes to pack for a trip and I organize things so that I rarely have to worry about forgetting something day of (which I would undoubtedly do otherwise).
- For this one week trip, I’ll only bring two pairs of quick dry pants, one jacket (that I’ll be wearing), one pair of shoes (that I’ll be wearing) and one or two long-sleeve shirts. I tend to work out daily, so the bulk in my carry-on will be socks, underwear and undershirts that allow me to exercise and still live life as odor-free as possible.
- I have a travel toiletry kit that duplicates everything that I use at home in small bottles. I replenish it when I get back from a trip so that, when I need to leave, I just put the whole kit in my bag and know that I’m good to go.
- I do the same thing with power cords and try to have a duplicate of everything that I need, including a travel adapter, hanging out in my suitcase so that I’m not moving cords back-and-forth.
- I try to keep my carry-on electronics to a minimum: laptop with extra cord, Kindle, two sets of earbuds (because I lose them constantly), charging cable and a backup cellphone battery.
- I don’t need to waste time retrieving checked baggage. I’ll fit everything into a bag that I can take with me onboard almost all airlines.
- I always travel with my Schwab Investor Checking debit card, which waives ATM fees worldwide. This has the dual function of eliminating fees so I can carry less cash (by making smaller withdrawals) and also keeps any potential loss to a minimum should I fall victim to some sort of ATM scam/skim. I usually keep a couple hundred bucks in the account so that I automatically know there’s something in there when I arrive at a new destination (as there’s a four-day waiting period for deposits to be credited after they’re initiated – and I’m not transferring anything additional in advance for this trip because, you know, it’s last minute).
- I always have and bring some sort of prescription traveler’s sickness medication (ie, Cipro). I rarely need to use it, but on those occasions that I have, it’s been a lifesaver…and I won’t have time on this challenge to stop for a day or two because my tummy’s ruffled.
- Usefully diversify points and miles: As you’ll see from the inventory below, I always try to keep my points and miles spread around a variety of programs, keeping redeemable amounts in all the big hotel chains, domestic airlines and transferable currencies (and away from smaller, more obscure programs). This is mainly so I can book fast if I find an award I want and don’t have orphaned miles in programs I rarely use. I think that it will also be handy here, when both price and available inventory will likely be stretched.
- Note that I highlighted “redeemable” above. If you don’t earn a bunch of points/miles throughout the year, it will usually be better to concentrate them into usable amounts within fewer programs. That’s not my situation, so I want to spread everything out just a bit more.
- Use the tools I have: When it comes to being a walking, talking award chart, neither Greg nor I can hold a candle to our friend, Nick Reyes. Nick seemingly has photographic memory when it comes to these sorts of things, and can instantly recall the intra-Asia 500-1000 mile business award price for obscure programs at the drop of a fedora. That’s not me. There’s a reason that I write this stuff down. What I do have is award search tools that I know well and use often. These tools allow me to search multiple programs, alliances, regions and routes fairly quickly and with a high degree of accuracy. My favorites (that I will be using during the challenge) are:
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- Seats.aero – probably the search tool that I use the most often as it allows me to search broad swathes of program-specific availability incredibly quickly
- Pointsyeah and Awardtool – great for drilling down on specific routes over a shorter window of dates
- MaxMyPoint – excellent for hotel availability, with a good mix of search filters (see: Tools for finding impossible hotel awards)
- MaxFHR – the best that I’ve found to quickly look at Amex Fine Hotels and Resorts availability, filterable by price range
Ways that I’ll be challenged during Flying by the Seat of our Points
There’s a few things that will keep me on my toes (literally) over the next 7-8 days. Here’s a couple that I’ll need to negotiate; one by birth, one by choice.
- Sleep: As Greg noted in his prep post, Nick is made for these sorts of trips. Not only doesn’t he need much sleep to begin with, he has the uncanny ability to almost instantly fall asleep the moment he sits down in a plane, train, car, boat or ox cart. Greg does need a good amount of sleep each night to avoid turning into The Frequent Pumpkin, but he shares Nick’s gift of being able to sleep when opportunity strikes (as you can see here). Unfortunately, I’m the exact opposite. I have an occupationally inconvenient inability to fall asleep in any sort of upright position regardless of how tired I am. I can even struggle to sleep for a decent amount of time in lie-flat seats. Because of this, I know I’ll probably be tired after a couple of days. The primary way that I plan to combat this is to exercise daily and, like Greg, I’ll have some sleep aids with me in case I need them on flights or while jet-lagged in hotels.
- Avios: Confession time. My Avios programs are a mess. This is most likely because, when I set each individual program up, I probably used slightly different info in the registrations. What this means now is that I can’t transfer between any programs except for British Airways and Qatar. I was going to fix it months ago, but there was that whole not preparing thing. So I left it broken and won’t be able to consolidate Avios for the challenge and will need to rely on separate transfers if I want to use any of the Avios programs.
Inventory (Points, Certificates, Credits, Lounge Access)
Last Updated: 6/3/24
I feel pretty good about where I’m at with my points and miles balances currently. I’ve got a good chunk in each transferable currency, as well as in all of the major hotel programs – which should come in handy when it comes time to book lodging.
Transferable points
- Amex: ~1.5M points
- ~$150 in airline fee credits
- 2 $200 Fine Hotels and Resorts credits
- Centurion Lounge access
- Bilt: ~2K points
- Capital One: ~510K points
- $300 in travel credit
- Priority Pass access with restaurants
- Capital One Lounge access
- Plaza Premium Lounge access
- Chase: ~150K points
- Citi: ~350K points
Airlines
- Air Canada Aeroplan: ~32K points
- Alaska Mileage Plan: ~1.7M miles
- MVP 100K / oneworld Emerald
- International oneworld Business/First Class lounge access
- 4 Alaska lounge passes
- 12 MVP® Gold Guest Upgrades
- 2 one way AA international upgrades
- ~$900 in travel wallet (from Amex incidental fee credits)
- MVP 100K / oneworld Emerald
- American Airlines AAdvantage: ~850K miles
- Avianca LifeMiles ~14K miles
- Avios
- ~64K with British Airways
- ~50K with Iberia
- ~2K with Qatar
- Delta: ~390K miles
- Etihad: ~4K miles
- Hawaiian: ~3K miles
- JetBlue: ~16K miles
- Lufthansa: ~80K miles
- Southwest: ~175K points
- United Airlines MileagePlus: ~57K miles
- Premier Silver status
- TravelBank: $126
- Virgin Atlantic: ~45k points
Hotels
- Choice Privileges: ~45K points
- Hilton: ~1.1M points
- Diamond status
- 2 free night certs
- Hyatt: ~2.1M points
- Globalist status
- 2 free night category 1-4 cert
- 3 suite upgrade awards
- IHG: ~680K points
- Platinum status
- Marriott: ~500K points
- Titanium status
- 3 85K free night certs
- 2 Nightly Upgrade Awards
- Wyndham Rewards: ~315K points
- Diamond Elite status
Car Rental Programs
- ~2,600 Enterprise points
- ~2,800 Hertz points
Join Team Tim (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 Last Minute Travel Challenge? Prepare I will not! (Tim’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.