The 2024 Frequent Miler annual challenge is over, with Flying by the Seat of our Points being won by Tim (congrats again Tim!)
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!
Tim, Greg and Nick were the challengers, with me and Carrie being tasked with crafting the challenge and acting as judges. We certainly didn’t have the travails that Nick encountered along the way, but there were numerous challenges and dilemmas we faced when planning Flying by the Seat of our Points.
We received a number of reader questions and comments during and after the challenge about how it was designed, so we wanted to share a little more about the thought process behind it, the considerations we had and the challenges we faced.
New Challenge Locations
We’ve run several Frequent Miler challenges since 2019, visiting a couple of dozen countries between us during that time. Seeing as we’d been able to showcase a little bit of each of those destinations in the past, we wanted to pick countries for each of the guys to visit that hadn’t been included with past challenges.
Never Visited Locations
Once the Frequent Miler team had settled on the concept of the challenge, Carrie smartly had us all share which countries we’ve visited in the past. In addition to picking countries that were new to our challenges, we wanted to assign countries to Greg, Nick and Tim that were new to each of them too.
Similar Time Zones
With Carrie on Eastern Time and me on Alaska Time (i.e. 4 hours behind ET) during the challenge dates, it was already going to be a little challenging scheduling the live check-ins so that we could all be present. As a result, when selecting countries for Stage 2 where the contestants all went their separate ways, we wanted to keep them in similar time zones.
Picking Cities/Countries With Luxury Hotel Options
With ~25 countries out of the running based on their inclusion in past challenges, we made a list of cities and countries that we thought could be interesting to send them to.
That list was whittled down a little by our desire for there to be at least a few luxury properties that each contestant would be able to book.
Visas & Vaccinations
With this being a last minute travel challenge, the three of them wouldn’t have a chance to arrange visas and vaccinations ahead of time. That meant Carrie and I would need to select countries that didn’t require vaccinations and which offered visas on arrival if applicable.
Navigating Foreign Languages
Dublin had been one of the cities originally on the shortlist. In fact, we’d assigned it to Greg for a while before deciding to change his Stage 2 destination. While it wouldn’t have been a huge advantage, we figured that if Nick and Tim had to navigate foreign languages, Greg should too.
Heading West Vs Heading South Vs Heading East
One of our biggest considerations was which direction around the world to send them in. Our initial inclination had been to send them west to Southeast Asia; that would’ve provided the opportunity to book some good business class products, plus they’d have a great pick of luxury hotels for reasonably-priced award bookings.
Researching this showed it wasn’t a great option though. I checked flights to each of the potential countries we’d send them to, with Thailand, Malaysia, Indonesia, Hong Kong and Taiwan being high on the list of potential countries. First I checked flights for June (when we’d actually be running the challenge) and then looked at flight options on Google Flights for a day or two ahead of time to get a sense of what last-minute flights were bookable even though that displayed cash rates rather than award options.
For the purposes of Flying by the Seat of our Points, this suggested that sending them west at the start of the challenge likely wasn’t a good idea. Due to flight departure times, connection times and arrival times, it looked like too much time would be spent traveling in that direction, with very little time spent on the ground.
Another option was to have them all travel to different countries in South America. Travel time down there was less of an issue, but when researching flights from South America to Europe, Africa or Asia, it looked like we’d have a similar problem going from Stage 2 to Stage 3 with this option as we would with Stage 1 to Stage 2 if we’d sent them to Southeast Asia first.
Another option was Western Europe to Eastern Europe, but this seemed like it would be less challenging on the flight front.
A fourth option was to send them all to Europe, then have them backtrack to send them all to Mexico City where they’d meet up.
Ultimately though, it seemed like US > Europe > Southeast Asia was the best overall choice. Travel times should be reasonable, they’d fit in well with our hoped-for livestream check-ins, there should be some good business class flight options from the US to Europe and then Europe to Asia, plus there’d be plentiful luxury hotel options for them to choose from.
Once we’d settled on that general routing, it was time to pick all the cities the contestants would have to fly to.
Picking Domestic Convergence Destination
Now that we knew they’d be flying to Europe for Stage 2, we needed to pick their Stage 1 destination. This was known as the Domestic Convergence because all three guys would be meeting up in the same city in North America.
A major east coast city like New York, Boston or Washington D.C. was under serious consideration. This would have the benefit of plentiful flights to Europe, with hopefully great business class award availability. Carrie and I decided against that though as we wanted the challenge to be, well, challenging.
Picking a North American city that wasn’t in the US was something under brief consideration, with Vancouver, Toronto and Mexico City all being options on that front. While that could’ve made things more interesting, we decided starting them in one of those cities would have less utility for Frequent Miler readers who are primarily based in the US, so you’d benefit more from them finding awards originating in the US.
Another option was picking a good-sized city not on any of the coasts such as St Louis, Cincinnati, Austin, Denver, Indianapolis, etc. Several readers advocated for that, or for an even smaller location like Des Moines. This type of location was a strong consideration, but we decided to go a different route.
That’s because a complaint we frequently hear from readers living on the west coast is that it can be extremely hard finding business class award availability to Europe from there. We didn’t doubt that was true (in fact, Tim already experiences this seeing as he lives in the PNW), so we thought it would be interesting – and challenging – to have the guys set off from there.
We didn’t want to make it too challenging though, so we sent them to Los Angeles as that has better international connectivity than other west coast cities like San Diego and Portland.
Sending the three of them to the west coast for Stage 1 also had another potential benefit. We thought that they’d assume they’d be getting sent to Asia next, so we’d get to surprise them when we revealed their European countries. That plan worked up until the last minute when Greg and Nick guessed that they’d be sent to Greece and Sweden respectively rather than the Asian cities they’d originally anticipated.
Similar Connection Requirements
In addition to making things challenging, we wanted to make things fair. We didn’t want to assign a country to a contestant where they’d have to take 2-3 flights if the other two guys would potentially have numerous nonstop booking options.
This didn’t quite work out as Tim did have one potential non-stop option pending availability, but we didn’t feel like that limited option would give him much of an advantage over Greg and Nick.
Contestant Comments
We’d considered a few different European cities/countries for Greg and Nick. Dublin, Lisbon and Greece had been on Greg’s shortlist and Bulgaria had been one of the countries on Nick’s. With Tim, we had fewer options as he’s visited most countries in Europe and so we’d already settled on Geneva or Zurich (both in Switzerland) for him.
We’d somewhat settled on Athens for Greg, Sofia for Nick and Geneva for Tim. However, during an Ask Us Anything livestream before the challenge we’d asked the three of them where they thought we’d send them. Nick said he hoped we didn’t send him to Europe, so that made us reconsider Sofia, Bulgaria for him. We wanted them to all be in a similar time zone and have similar travel times, so we looked at North Africa. He’d visited Egypt during a past challenge and Tunisia didn’t have a ton of good hotel options for the purposes of the challenge, but Morocco did have a number of hotel choices. Morocco also had the benefit of being classed as part of Europe by Air France/KLM Flying Blue, so that might provide an interesting award booking option.
I therefore researched flight options from LAX to Marrakech and Casablanca and there seemed to be several that would work provided there was award availability. Failing that, I figured he’d be able to get to Europe and catch a cheap flight from elsewhere or take a ferry from Spain, so we gave Nick his wish of no European country.
Cities Vs Countries
We continued to consider different European cities for Greg, Nick and Tim in the weeks leading up to the challenge.
We’d had Lisbon as Greg’s choice for a while, but then Carrie suggested that we pick somewhere in Croatia for him. Flight options in and out of Croatia seemed to work, but this left us with a dilemma – which city should we pick for him to visit? Split and Dubrovnik are both on the coast and each had a couple of interesting-looking hotel options via Amex Fine Hotels + Resorts and more. Zagreb meanwhile had better flight connectivity.
We had similar dilemmas for Tim and Nick. Should we send Tim to Geneva or Zurich? Should we send Nick to Marrakech or Casablanca?
We ended up coming up with what we thought was a good solution. Rather than giving each of them a city to visit, we’d assign a country. That would maximize their flexibility, thereby allowing them to book the best flight options, while also picking a city with hotel award options and attractions that interested them.
Asian City
After visiting Croatia, Switzerland and Morocco, we knew we’d be sending them to meet up in the same location in Asia, but which Asian city should we pick? Our decision was made a little easier by our self-imposed requirement that they only visit places none of them had spent time in before. Kuala Lumpur was the clear winner as somewhere that none of them had spent time in in the past, while having good flight connectivity and lots of luxury hotels to choose from.
Exploration Challenges
For each of the stages, we wanted to assign them some kind of Exploration Challenges. This too provided its own challenge for us. We’d need to assign tasks that were somewhat destination-specific in order to highlight the places they’d be visiting. However, we wouldn’t know ahead of time which cities they’d be visiting for Stage 2 and so the Exploration Challenges couldn’t be too specific there.
Carrie ended up doing a wonderful job with this, crafting fun tasks for each of the guys to complete that showcased the countries they were in but which would be achievable no matter which city they’d end up in, such as Nick needing to eat something in a tagine and Tim drinking absinthe (which is from Switzerland).
Livestream Timings
For each of the stages, we’d be checking in with the contestants live on YouTube. I mentioned in the Time Zones section earlier that Carrie would be on ET and I would be four hours behind in Alaska. This made things challenging when it came to choosing what time to arrange those livestreams, especially when it came to whether or not we should disclose those timings ahead of time. If we shared the timings ahead of time, the guys might get a sense as to where we’d be sending them. Not disclosing those times would make it harder for readers/viewers to watch the livestreams if they weren’t given much notice as to when they’d be. In the end, we decided to announce the timings ahead of time and hoped Greg, Nick and Tim would still be somewhat in the dark about where they’d be sent.
Our normal livestream time is 9pm ET, but that would make it 2am or 3am local time for them when in Morocco and Europe respectively. That seemed potentially cruel, although jetlag might’ve made that possible. In the end though, we settled on the much more reasonable 2pm ET which was 7pm and 8pm respectively for Stage 2.
For Stage 3, we wanted to plan the livestream at the very end of the challenge so that we could announce the winner during the livestream after we’d had a chance to award points for their hotel bookings and Exploration Challenges there. The time zone difference worked in our favor with this. Malaysia is 12 hours ahead of ET, so scheduling it for our normal livestream time of 9pm ET meant it would be 9am for Greg, Nick and Tim – late enough in the morning for them to have had breakfast, but early enough for them to catch a flight out later that day if they found some kind of great award flight for their way home.
Questions?
Carrie and I had many lengthy discussions about plans for Flying by the Seat of our Points, so I’m probably forgetting other considerations that we had when planning the challenge. Is there anything else you’d like to know about how the challenge was organized or why we made the choices we did? Let us know in the comments below.
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