Frequent Miler on the Air - Our worst travel challenge moments | Coffee Break Ep13 | 6-4-24

Episode Date: June 4, 2024

(00:00) - You know that sinking feeling when you know things are going wrong? With a brand new travel challenge just launched last night, we've got our past travel challenge snafus in mind. Coffee Break: Our worst travel challenge moments (02:53) - 40K to Far Away Learn more about the 2019 40K to Far Away Challenge here. (03:09) - Greg: Train breaks. Bus breaks Read Greg's story about his South African misadventures here. (06:18) - Nick: Asleep on bus, can’t enter Bangkok, bike ride to nowhere Read about Nick's misadventures during 40K to Far Away here. (11:20) - 3 Cards, 3 Continents Read more about the 2022 3 Cards, 3 Continents Challenge here. (11:46) - Nick: Canyoneering (12:48) - Greg: Air Canada married segment problem, then wouldn’t let me check in Read more about Greg's married segment problem here. (16:22) - Party of 5 Read more about the Party of 5 Challenge here. (16:52) -Greg (and Nick): Santiago, arriving at the Ritz w/out a backpack Visit here to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media. You’ll find all other Frequent Miler on the Air episodes here. Music Credit – Beach Walk by Unicorn Heads

Here we go. This is not your typical Frequent Miler on the Air episode. This is a standalone segment we're calling Coffee Break. Each Coffee Break segment will cover a single topic related to miles and points. And each Coffee Break is limited to 20 minutes or your money back. Enjoy. Today's Coffee Break, our worst travel challenge moments. You know that sinking feeling in your gut when you're traveling and something went wrong and it takes you, it dawns on you like slowly. It takes you a while to realize that like

all heck has broken loose and your great plans are now fully awry. That's what we're going to talk about today in terms of things we encountered on our past team challenges when things went terribly wrong. Hopefully this is not foreshadowing because we are about to kick off on our 2024 challenge, our Frequent Miler Team Challenge. In fact, when you can first listen to this, when this first publishes, we will have just known about where we're going to meet for our domestic convergence. So we're going to be meeting up somewhere,

Greg, Tim and I on June 5th. We don't know where as we record this, but by the time you listen to it, we'll know where we're going to meet up domestically on Wednesday, June 5th. And then we're going to live stream on YouTube at 9 p.m. Eastern time on Wednesday, June 5th. Is that right? 9 p.m. I hope it's right. Yes. And we will find out from Carrie and Steven where each of us will be going internationally. We're just going to

take off somewhere internationally and we're going to have travel challenges that we have to meet. And then after we do that in each of our own individual international destinations, Carrie and Steven will give us an international destination where the three of us need to meet up again. You're going to want to follow along on Instagram to see all the adventures, all the travel challenges, and to see us find out in the moment live where we're heading next. And of course, then we're going to have to scramble to book something, flights, hotels, trains, planes, whatever it may be, in order to get to where we need to go. So there is a lot of room for potential hangups in last minute travel. So maybe today's episode is really just to help us walk back through how we fixed our problems so

that we can hopefully handle them this time around. I don't know. I'm not sure about this topic. I'm a little nervous. Maybe this is a sort of rehashing lessons learned so that we don't make the same mistakes. But yeah, it's likely. It's very likely that we'll encounter some similar. I mean, they're not going to be the same, but things are going to go wrong for sure on this challenge. And hopefully it won't be too bad. I thought you were going to say, hopefully it won't be my trip. Well, that's true too.

Yeah, that goes double for mine. But we're going to go over the last three challenges and talk about the major things that went wrong and how we dealt with them briefly. The first challenge we're going to talk about is 40K to far away. That's where we each had 40,000 points and $400 to travel as far as possible. And in that case, we were traveling mostly in economy because the points go much further that way. But in my case, I had arranged a lot of my travel around the fact that there is a sleeper car that you can take from Johannesburg all the way to Cape Town, South Africa. So that's a long overnight journey and it's only $50. And so I sort of arranged my trip around this. And so I made it onto the train and the train was going fine

until it didn't. The train literally broke and broke down. Well, yeah, it broke, but that's not where the bad ended, right? I mean, the train broke down. That's bad luck, right? I mean, but that does happen on trains from time to time. And, you know, it would be a minor annoyance if it were only for a little while or if that were the entire story. But it's not, right? Yeah, no, it's not.

They got the train, like, moving in fits and starts. So it was quite a while before anything happened. But eventually the conductor came around and said, you have a choice. You could wait here for, we don't know how long to, until the train is fixed or we're sending buses and you can, you can take a bus the rest of the way. I mean, that seems like a much better idea than waiting around for the fix of broken train, right? Well, yeah. Plus I had a, you know, my challenge wasn't over. So I had a plane to catch the a day later. So I had to get to Cape town before going on to the next journey. And so,

so I took the bus and, and the bus was going along and then all of a sudden we hear a big crash and we're like, what is that? And the bus pulls over. We're still like all kind of looking around like what's going on? The driver and a guard who was on the bus get off and are walking back down the road where we were. And I look out the window and I look back,

a big piece of the bus from the roof was on the ground back there, had somehow fallen off the bus. Woo! Roof lies off. Yeah. That's some rough luck there. Right.

Luckily, it turns out a roof isn't necessary for a bus to work. So eventually we got rolling again and made our way to Cape Town. It's not an operational piece. It's not a must. It's just a luxury. So you just, you know, a luxury. So so you could deal with that a little bit of roof, probably. So, yes. Who needs a roof?

I mean, did they put the roof back on or did they just leave it there? What happened with the roof? They strapped it to an SUV came and they strapped it to an SUV with like giant duct tape rolls. As one does. As one does. I mean, you never know when the next bus is going to come by and need a little extra roof. So there we go. That's so you made it though. You made it to Cape town and you had to do something there, right? Oh yeah. Actually we had a great time. All that went really wrong

in Cape town is we had a dinner much later than expected. And because it was really our plans for doing stuff in Cape town were the next morning. And then I flew out the next afternoon. So it worked out fine, actually. Well, there you go. But it did add a little bit of drama for a little while. I imagine you were sweating it a little bit sitting there on the broken train and then on the broken bus. That's a rough train of events. Speaking of a rough train of events, my 40K to far away trip had some low lights, I guess you would say. There were a few moments

that didn't work out well. I'm sure a lot of people remember me sleeping on the concrete slab outside of the Honolulu airport. That really wasn't that bad comparatively. I wouldn't even consider that among the low lights. So before I ended up on the slab outside of the airport, I was taking a bus to the airport because I was trying to stay awake desperately while I was working in the lobby of the Hyatt place that I wasn't staying at, but I had a key left over from a previous day. So I had that sitting on the table. So security wouldn't bother me as I worked late at the Hyatt place in the lobby. But I got so tired, I was having a hard time keeping my eyes open. I said, OK, I just need to take a bus to the

airport. So I'm there at least. And that seemed like a great idea until I woke up well past the airport stop or whatever stop I had to get off at. And I realized I have no idea where I am on this bus. And it pulled into a bus station and was like, OK, this is the final stop. And I'm like, the final stop? Like, is the bus done for the night? Am I just stuck in the middle of nowhere? This like bus station and, you know, bus stations are not always in the like most glamorous part of town. And so I was nervous, a little nervous when I woke up out of a dead sleep to that, but it worked out. And you had to get to a flight, right?

I did, but not until morning time, I think. And it was like three o'clock in the morning. My flight, I don't remember what time it was, but I had plenty of time to get there. I just wasn't even sure where I was. And then I took a look and it wasn't particularly close to the airport, but luckily there was eventually another bus, I guess, because I did get to the airport. It just wasn't quite as quick as I thought. And I ended up having to sit on a bench at the outside the bus station for quite a while, but, but, you know, it worked out all well, worked out in the end on that one. What didn't work out was that I, after I flew on from there to Tokyo and then to Bangkok, I flew from Tokyo to Bangkok to Brisbane on an AirAsia ticket.

And I got to Bangkok and I had this plan for where I was going to go because I could get somewhere like cheaply on a tuk-tuk or something from the airport. How long was your layover? Oh, it was eight, eight hours, I think something along those lines, eight or nine hours. And and it was the not the larger Bangkok International Airport, but the smaller one that's a little closer to the city, I guess, the DMK airport. So I thought, oh, this is great. I can take a tuk tuk.

I can go get some street food. This is going to make for some great Instagram footage until I went to exit the secure area and they wanted to see my boarding pass. And I had to dig it out and find it. And then they were like, oh, no, you can't leave the airport. And I was like, what do you mean I can't leave? Of course I can leave the airport. And they were like, no, on this kind of ticket, you can't leave the airport. I'm like, but I'm American. I don't need a visa to enter Thailand. Like I can go in. This is not a problem. And but no, it was apparently a problem. And what I've since learned is I think AirAsia, one of the ways they stay so cheap is they

don't they don't pay some of the taxes that you would ordinarily pay to transit certain places. And so, for instance, there they weren't. I think the problem is that they weren't paying the taxes or thereby I wasn't paying the taxes to enter Thailand just to transit Thailand. And so I could not leave the airport because those taxes presumably were not included in my ticket and there was no way to pay that or anything. So I got stuck in the Bangkok airport for the eight hours or so. And it wasn't even, again, the major international airports, the smaller,

less glamorous of the two Bangkok airports. So, I mean, I solved that by using my Priority Pass membership to get a free head and shoulders massage in one of the Priority Pass lounges. I did a little Priority Pass tour in that Bangkok airport that was not all that good, but I did it. And then my last little low light was my bike ride to nowhere. And that was in New Zealand. I had, again, an eight or nine hour layover in Nelson, New Zealand. And there's a bicycle rental shop directly next to the airport. Like literally you could throw a stone pretty hard and hit the airport. And so I rented a bicycle and I took this long ride, 20 miles or whatever, to get to a ferry so that I could go see something cool.

And I got to that point as the ferry was pulling away. And I did a lot of bike riding for nothing. And of course, I didn't bring any food because I was going to eat on the other side where the ferry was. And I figured out there'll be places to get water or snacks or something along the route. Nope, not a single place. If I remember right, the pizza place was across the highway, right? And you couldn't get there. It was. It was like this huge multi-lane highway with like fences and stuff. There was no way to get across it. So yeah, it was painful.

Those last few miles getting back to the airport were painful because I had nothing to eat all day long. Yeah, that was, that was rough. Ouch, ouch, ouch. All right. Well, let's move it along to three cards, three continents. Everything went right in that challenge, right? Mostly. I mean, mostly. For me, actually, truth be told, it went pretty well. I mean, I think maybe if I were to look back at what went, it didn't even go wrong. I think my most disappointing moment was when I was done making the reels for the North Pole because I was like, man, I've been looking forward to this for weeks and it's done.

Wow. But no, I think in terms of something kind of going wrong on the canyoneering that I did in the Philippines and Cebu, Philippines, I am not particularly fond of heights or cliffs. And I did not realize, silly me, how much jumping off of cliffs would be a part of that day. And of course, once you've jumped off, you know, one or two or three, there's no climbing back up. So there's no way to get out of it. You just have to keep going down until you hit the bottom. So, so I, you know, after the first couple, I was like, I don't know if I really like this or this whole

idea. I'm there with one person who, you know, is significantly smaller than me. I wasn't sure he would be able to pull me out to a hospital or whatever if something went wrong. So I was not feeling super confident after the first couple, but there was nothing I could do. So all I could do is keep going forward, which, you know, I guess that's a metaphor for life, right? So yeah, keep going forward. It turned out fine, right? I mean, it did. I mean, I lived stressful time. Stress. Yeah. A little bit of stress, but out fine. Right. I mean, I mean, I lived stressful time stress, yeah. A little bit of stress, but it was, yeah. Three cards, three continents. Wasn't as smooth for me as you know. Um, I had booked around the world ticket using ANA miles and it was a star

Alliance around the world ticket. And the very last part of it was I arrived from Bergen, Norway to Newark airport. And then from Newark, immediately on Air Canada to Toronto, and then the next day, Toronto to Detroit. And that last segment, Toronto to Detroit, I had booked the morning flight, but what I really wanted was the afternoon flight because there otherwise wouldn't be any time to do anything in the Toronto area. And it was necessary for the challenge for me to do something in Canada. And so I thought, okay, I'll just set an alert for the award space to open up for that afternoon flight.

And I'm sure it will. And ANA lets you change for free as long as you have the same route and same carrier. And it did open up like about a week before called ANA. They're perfectly happy to change it. But Air Canada would not allow it to be reticketed that way. And the reason was the ticket, it was like a married segment logic thing that when they ticketed the part from Newark to Toronto to Detroit, it was ticketed as one flight. So that's how Air Canada had it recorded was a single flight with a layover in Toronto. to the Toronto to Detroit part to that other time, they would have had to cancel the whole thing, including the Newark to Toronto part, which was no longer available as an award. So I flew to

Toronto thinking that I might be able to get them to just give me a free standby on the later flight. They wouldn't. And then at the last minute, I booked an award ticket for that last segment, a cheap award ticket. And it was within two hours. And they wouldn't let me check in for the flight. So I'm at the gate going, come on, I just booked this. It's a paid for flight. Let me check in. They're like, no, sorry, two hours. That's our rule. And finally, luckily I went to, there's like this exceptions desk. I went there and at first the guy there also was like, no, there's nothing we could do. But then when I said I have global entry, so he had said there's not enough time to get through security for this. And when I mentioned I had global entry, he made me show him my actual physical global entry card, showed it to him because I actually had it with me. And he let me in and

I made it actually pretty easily, even with my bag getting flagged and them rummaging through my bag to see whatever my microphone or something was. So I did get in, but man, the whole Air Canada experience left a bad, was bad time for me. Yeah. Yeah. You know, I love Air Canada Aeroplan, but the one time I flew Air Canada, I also just had like a bad experience with, with just the way that things worked in the airport. Yeah.

The flying itself was good. Like I actually liked the onboard experience, but the, their processes and everything, they're so inflexible. It's really, really frustrating. Yeah. I totally agree. Killed me. I I'm, I've not flown again since, and that was probably more than 10 years ago. I've not flown with Air Canada 15 years ago. I haven't probably flown with them since, but anyway. All right. So, I mean, that that's, you know, we made it through. What about party of Five? Let's talk about Party of Five. Last year's challenge where we traveled as a team with all five of us.

Right. What went wrong there, Greg? Yeah. Yeah. So the worst moment was when I lost my sunglasses in a waterfall and I was like, oh, no, what's that? That was the worst moment of like day two of the trip. Later that same day, the worst moment was when everybody on the team saw the sea turtles but me. I don't know how you didn't.

It was like right there. Snorkeling. But no, the worst moment by far. We flew into Santiago, Chile. We got in a Uber. It was supposed to be an Uber Excel. But there was only four passenger seats and there were five of us. So four of us had to cram in the back seat.

So I put not just my suitcase, but also my backpack in the trunk. And we drove to the Ritz Carlton and we got there and we got all our bags out. And I kept looking, where's my backpack? Where's that backpack that has like everything? Luckily, my passport was in my pocket. My wallet was in my pocket and my phone was in my pocket. But there's a lot of stuff that I needed in that in that backpack. And it wasn't there. It was at the airport. Yeah. And that led to like an entire day of well of bouncing from police station to police station as we tried to get the police to bring us to where the you know, where it showed on the map that Craig's AirPods were,

because he could see that on his phone. And we figured, well, maybe his bag is traveling with somebody and we can find them and get it back. And that was a challenge to get a police officer who would entertain that thought to begin with. And then we were bounced like one precinct to another because it kept moving around. The police weren't allowed to go to another precinct. And so when the AirPods kept moving to other precincts. Right. Right. But we did finally get like after all day long of this, we did finally get someone to drive us around in the cop car. So we did get a ride around in a cop car in Santiago and like stop somewhere on the street. And they made someone open their bag and everything. You know, a little bit of excitement. But yeah, for me, that my little light would be when Greg's bag got stolen in Santiago

because I obviously felt bad for Greg and it made for a not so much fun day. And of course, Tim had planned a pretty incredible day of whitewater rafting in the mountains and sunset at a hot spring in the Andes Mountains. It was going to be pretty awesome. And of course, we couldn't do that. Although, truth be told, I think like half the group at that point was probably not feeling

very well, like people have been coming down with colds by that point. So maybe it was all for the best. But hopefully this trip goes a little bit smoother. But we're almost out of time and I don't want to have to give any refunds today. So don't forget, follow us on Instagram, FrequentMiler. Join our FrequentMiler Insiders Facebook group and check out frequent miler on the air dropping every Friday. Follow us on the challenge and we will see you guys soon. We'll see you on the challenge. Bye everybody.