Frequent Miler on the Air - 100K Vacay Livestream Kick Off | Frequent Miler on the Air Ep326 | 10-3-25

Episode Date: October 3, 2025

Greg's benchmark trip is done, and that means it's time for the 100K Vacay team challenge to begin! In this episode, you'll get a chance to listen to the kick-off live stream that aired on October 1st at 9 pm Eastern Time and reviewed all the things that went well (and could have gone better) with Greg's 100K Vacay benchmark trip to Malta.(01:14) - Here's the timeline of the challenge (starting with the October 1st live kick off).(03:14) - What is 100K Vacay?(03:54) - What's the deal with Greg's benchmark trip? Why isn't he being judged?(06:26) - Greg's benchmark trip - what was it and how did he do?(28:20) - Greg's final totals for his trip and why he scored himself a B+You can read Greg's trip journal here.(35:43) - How do our competitors feel? What are they confident about, and what are they less confident about?(53:08) - How do Nick and Stephen feel about the fact that Tim's already hit the ground running?(1:00:35) - Redemption on VS in Europe is distance-based, not considering layovers (something you advocated). Is it worth the extra time to save some miles due to layovers in AMS or CDG?(1:03:01) - How did you end up in Business Class on Air Serbia? I never even heard of it before.(1:04:29) - How was the breakfast at the Hyatt Centric Malta? Did they have local food?(1:04:27) - Did any of your trips take advantage of mileage transfer bonuses?(1:05:32) - How was the breakfast at the Hyatt Centric Malta? Was there local food?(1:06:25) - Was there anything you would do differently?Subscribe and FollowVisit https://frequentmiler.com/subscribe/ to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media.Music Credit – “Ocean Deep” by Annie Yoder

This is a Voyescape podcast. You can find all of our travel podcasts from around the world at voyescape.com. The 100KVK Team Challenge begins. Frequent Miller on the air starts now. My benchmark trip is done. I spent four nights in Malta, and in today's episode, I'm going to give you a full overview about that. We'll discuss what went well and what didn't. And then we interview challengers.

For each contestant, we asked, are they confident or quaking? Now that they've seen what my benchmark trip looks like, we learn that both Tim and Stephen are starting in New York City. This is kind of ironic because Nick is the only contestant who actually lives within easy driving distance of New York City, but we don't know where Nick is starting. and we also learned that Tim kick things off already with a daytime flight and you'll learn all about that in today's episode. If you're interested in following along and you should, make sure to follow Frequent Myler on Instagram. That's where the stories and reels are presented in as close to

real time as we can and it really brings the challenge to life. That's where you'll get all the excitement of the challenge as it unfolds. Here's the timeline of the challenge as far as you need to know it. On Wednesday, October 1st, that's a couple days ago as this is published, we did a live stream where Carrie and I and all three contestants met to kick off the contestant part of the challenge. And Saturday, October 4th at 6 p.m., we're going to do a mid-challenge check-in. So that'll be another live stream. Make sure to follow Frequent Myler on YouTube if you don't already, because that way you'll get notified about this live stream and all the others that we do regularly. That'll be our chance to see where the contestants are at that moment

and to interview them about how the trip's going so far and what's next if they're willing to divulge any of that. And we will also, as judges, Carrie and I will give preliminary ratings for how well they've done. Finally, on October 8th, at 9 p.m. Eastern time will be the final challenge live stream and that's where we will crown the challenge winner. So be sure to check that out because we will, of course, discuss each contestant's trips and find out then what went well, what didn't and crown a winner. So without further ado for the rest of this episode, what follows is the recording from Wednesday night's live stream. All right. Welcome everybody to frequent mylers. Ask us anything, but this is a special

episode where we're going to be launching our 100K vacay challenge. Wherever you're watching, you're listening, don't forget to like, give us a thumbs up. Leave us some stars if you're listening in podcast format, all right? We always appreciate that. Leave us a comment or review. Let us know what you think. We're obviously going to be talking and taking questions live on YouTube as we record this. But if you're listening to it later on, don't be afraid to comment on the post or the

podcast or the YouTube video, wherever it is you're watching. So now I'm going to kick it over to Greg to tell us about the 100K vacay. All right, great. So every year we do a team challenge where we compete to see who can make the most of points in miles. And each year we make up a different game. And this year's game is we each, each challenger has 100,000 transferable points and a budget of up to $1,000 cash that they can use to build the most incredible vacation. possible. And there's some rules involved in that that we'll get into some of that. But this time there's something very different going on, which is that I am not a challenger, but I did do

a 100K vacate trip. And the purpose of the trip that I just got back from was to set a benchmarks of what the challengers are going to be trying to, like, beat all the components of what I did. And one of the reasons we pulled it out is because we have each, we pull, one of the reasons we pulled it out is its own separate thing, is that each challenger has a certain type of transferable points. one person has American Express, one person is city, another person has Capital One, and then there's Chase. And the problem with Chase is that it has to do with how we design the rules

of the challenge. And one of the rules is that you have to spend at least three nights in proper lodging. And Chase is only one of these four transferable currencies that transfer to Hyatt. Well, why does that matter? Well, If you think about what it means to spend three nights in a hotel, what it means with most point systems, like let's take Marriott, for example, typically a decent hotel will cost at least 30,000 Marriott points. And so if you transfer your Amex points, for example, to Marriott one to one, and you book a 30,000 point hotel for the required three nights, then that would take up 90,000 of your points, and you'd only have 10,000 left over to actually get to the hotel and get back to where you started. Hyatt, though, they have an award chart that starts at only 3,500 points off peak, and so

there are some great value to be had for very few points. We felt like Chase has a big advantage. So we pulled it out as a separate thing. Like the person who uses Chase points, will set the bar, and then the others will try to meet it. Yes, great. And you just finished setting the bar, right? I did. I got in this morning at around one. Yes, that's right.

I know that well because I was there, and I also got in this morning around one. So I want to hear a little bit about what was that trip? What did you do? And how did it go? Oh, come on. You know all about it. well you got to tell the royal we where did you go and what did you do

yeah where did we go and what did we do so I started my trip we were allowed to start our trips from anywhere we wanted and it would have been really convenient for me to start from New York but I wanted to make my trip as applicable to many people as possible So I started at my home airport, Detroit, and paid for a positioning flight to New York City, and I counted for that in the budget. And again, I did that because, like, I figured that almost anywhere around the country, it's possible to get, it's often possible to get cheap flights to New York City to position to go onward. So I feel like that made it more applicable to many people. So anyway, so I started in Detroit, flew to New York.

I met up with Julian, who's the founder of Points Path, but also a good friend for many years, and it's become a tradition for us to meet up on these challenges. I first met up with him in New York on 40K to far away, and then again on the SAS Million Mile Madness Challenge. So this was the third time in a row. also met up with Kerry there because as a surprise to our audience and to the competition here, or the competitors in this challenge, Kerry decided to come with me on this trip when I asked her if she'd like to. And so we actually met up at the TWA Hotel at JFK. And I had never been there before. Carrie hadn't either. It's crazy fun actually to hang out there for a little while. There's there's like ridiculous stuff like an old

hair salon from like 1962 that's that's all set up and you can go in and and you know sit under the dryers and chat about points and miles like Julian and I did. You can play a giant game of twister like Carrie did. You can you can do a photo booth. So we were playing around actually having a lot of fun. And ironically, the TWA experience became like sort of a mini highlight of the trip in a way. Then we said goodbye to Julian and flew off in business class to Malta. So we flew Air Serbia business class. We, let's see, yeah, we flew from JFK to Belgrade and then onward to Malta from there. In Malta, we checked into the Hyatt-centric for four nights. So the Hyatt-centric there was available for only 6,500 Hyatt points per night. So that didn't

put a big dent in my budget. And then we went off to, so this was the same night, The Friday night, we went off to a particularly scenic cove beach area on the island to watch the sunset. And there, Chef Bjarna, who I had met originally on the 40K to Far Away Challenge in Johannesburg, I had flown him in to join us in Malta. And so he had prepared a picnic with all kinds of local specialties. And these weren't like fancy food. These were like finger food type of things, the type of stuff you'd get at a street vendor and so on. And a huge array of that kind of stuff.

Did any of your finger foods have actual fingers in them? Not to our knowledge. We didn't, yeah. If they did, they were really tiny fingers. Okay, so they were mince fingers. So Rabbit is a specialty, is a food that's eaten. often in Malta, and so there could have been rabbit fingers that we didn't notice. I'm not sure. Is that cluster's lucky? Because like rabbit foot is, but like rabbit toes or finger? I don't know.

Lucky rabbit paw, yeah. I think so. Sounds like that would be lucky. And so that was, that was, I guess, a really fun to see people's reactions when we surprised people. But it was also just a great experience. I mean, to on day one, on get to try, like this huge assortment of local foods from the area that you're going to. What worked out great. And Bjorn is a lot of fun as well. So it was fun hanging out with him.

And the sunset cooperated. It was beautiful weather, beautiful sunset. So that was all fantastic. We were staying in the hotel is in a town called St. Julian's, which is not where I would choose to stay. if if i was going back to malta it is uh it's in the sort of party area of of malta and so you know if if you want to go out and party each evening it would be great location it's just not how i want a vacation um so you know that was that was not ideal but um it wasn't bad like in the hotel the it didn't bother me it's just that we had to get to the places we wanted

to Valletta, to Amdina, to the coastal things that we did. We always had to take a bus or a ride share, bolt instead of Uber is the most common one there. Or a ferry one time we took a ferry, but we had to walk to Slema to catch the ferry. Okay, so then over the next few days, we did two walking tour, two historic, historic walking tours. We visited the St. John's Co-Cathedral, and we learned why it's a co-cathedral, which I won't give that away right now. The Co-Cathedral had a really well-done art exhibit there that Carrie was particularly excited about. Do you want to explain that briefly, Carrie? Yeah. For years, my favorite artist has been Caravaggio, and when we went into

the church, I saw they were labeling some of the paintings and I just had a thought like, oh, what if one of these is a caravaggio? That would be cool. And then like two minutes later, there's this huge sign that says, Caravaggio this way. And they don't have just like tiny little labeled Caravaggio paintings. They have a room-sized Caravaggio painting. It's the largest one of his career. And then they had another one in the basement and they had this whole exhibit around it. And that's just like a bizarre thing to not know ahead of time and just stumble upon your favorite artist's largest work of their career. That was just super cool. Yeah. So, you know, my planning Malta was all because this was Carrie's favorite artist. And of course, I somehow knew that

in advance. Somehow knew that. Gosh, you're so good at the surprises, Greg. Can you name your favorite Caravaggio painting, Greg? It's a really big one in the room. That's why you didn't book the tickets ahead of time and we almost skipped it? That's right. That's right. That was all a fake-it-out, yeah. Anyway, that exhibit was so well done. I don't know anything about art, really, but I really enjoyed that art exhibit more than just seeing the cathedral itself, much more. Did I mention we did? So we did that. We explored catacombs.

We, um, uh, we, we, we sampled like the best, um, oh shoot, Ptizi, uh, in, uh, in, in, uh, in Malta, or at least that's what, uh, we were told that this was, this place was best and it was, it was excellent. I believe it. They're like, um, they're sort of like, uh, hot pockets, but much better. Right. So you've got the bread on the outside. I'm going to let me say the Pistisi people would not appreciate. I did say much better.

True, of course. And different places have different kinds of fillings in them, but the two main fillings, one is a cheese filling. The other is like a smash pea filling, which doesn't sound that great, but I actually thought that was my favorite of the two. Yeah, think like curried peas. Oh, nice. That makes it better.

Yeah, yeah, that's a better way to think about it. So would it have been like chicken, how he'd Peas? No, it was like green peas, yeah. But it was really good that way. That was pretty close to my only vegetables for the whole traffic. Yeah. So we did two days of that kind of sort of like historic type exploring. Going around, Amdina was fascinating. That's a medieval walled city that's really well kept up and it's just so cool. I don't know. Anytime I've gotten to see a walled city, you know, that's in pretty good shape. I love that.

And Valletta, which is the capital, I thought that was gorgeous. You look down at the water from different parts. They have a lot of, it's not nearly as old as Amdina, but they have a lot of old architecture that makes it very pretty. And the history there was just so interesting. saying, I don't want to give stuff away for anyone who's going, because I think it'd be, I think that was part of the experience was learning about it while we were there, made it like really super cool.

I didn't know how much I was interested in history until I was learning about this stuff being like, wait, wait, what happened with the Knights? Is that true? You know, it was, it was crazy. But one little thing is Caravaggio was fleeing from Italy. He, like, killed someone, right? Yeah, he murdered something. The knights of Malta took him in, and as a thank you, he painted that gigantic painting that Carrie mentioned.

Yeah. It might have been a required thank you. So it was blackmail, really is what you're talking about. He was a provocative character. Yeah. So, okay, so we did those things then. We had to do water activity. What the main touristy water activities is to do these tourist boat trips that go to different.

The Malta has a few islands, and they usually stop at set places. There's one place called the Blue Lagoon, there's another something grotto, and I was really mixed about whether we should do that or not. I hated the idea of being like with mobs of tourists, and that's what all the, everything I read said, you know, you can't avoid that. So I found another option that was a local hidden gem spot, which was a cove with caves like right there. You walk right up and into these caves that are along this cove and there's enough like rocks in a semicircle around the cove to shelter this cove from any waves or anything. So you have nice still water for swimming.

Scuba divers, which we didn't do, but scuba divers go in right where people who are swimming go in, but then they can swim through tunnels in the rocks that are right there like 20 feet from where you get in the water. And as we were swimming around, put your face in the water, not only do you see fish, but you see scuba divers too that you didn't know we're there, which was kind of a neat experience. And we hiked a little bit from there up on the cliffs above this area. And that was spectacular. And all this, like, we didn't see any tourists. There were locals there.

And it was just, when we're hiking, there was nobody. It was just us. And it was so perfect. It was exactly how I want a vacation, that kind of thing, rather than the tourist mob. So that was really perfect. And then we met up with the next. surprise the final surprise of the trip was was maisie the culinary concierge who accompanied me in the three cards three continents trip i had invited her to come and um it turned out she wasn't able

to arrive on friday like the rest of us did because she was in los angeles for a relative's bar mitzvah and obviously she had to do that um and so you know i thought we'd okay we're going to have to call it off because she wouldn't be able to get there until Monday, which was the day before Carrie and I would be leaving. But then I learned that she was pregnant. And I thought, what an awesome baby moon gift I could give her is use my points to give her this vacation. She was super excited about it because she and her partner were able to come fly out Sunday night, arrive on Monday. And And we then we used my suite at the hotel to do some sort of like interviews to talk to both Maisie and Bjorn about what it's like traveling with Greg and, you know, what they thought when they got these invitations and everything like that. So that was fun.

And we then went to the tallest tower. One nice thing about St. Julian's, where the hotel was, is the tallest tower in all of Malta is there. And it has this two-story rooftop bar. And if you go, especially, well, actually, either level has just stunning, stunning views. And the top level also has a walkout area that's glass-bottomed. And some of us were happy to walk out there. Some of us not so much. But I loved it.

that was free they let us come up and look around even though we weren't like buying drinks or anything because we had a a reservation to get to which was at a restaurant in Valletta which was a it's a restaurant that does all Maltese dishes and the seven-course tasting menu of all Maltese dishes all locally sourced and And it's only $48 euros per person for the seven-course elaborate dinner. So that's very reasonable for that level of cuisine. It was fantastic. I don't know about you, Carrie, but I made the mistake of eating too much of the

yummy stuff early on. And so by the time I got to my favorite dish, I could barely eat any of it. And it was really disappointing because everything had been so good. but then I got to that one. It's like, oh, this is great. And not so much, you know, I just couldn't do it. Yeah. I was super impressed with how seamlessly they modified for the varying dietary restrictions at the table because we kind of had a lot. Maisie's pregnant. So she has to, you know, eat certain things, not eating certain things. And her partner can't eat dairy. And I'm technically pescatarian. And so I felt so guilty when he's like, dietary restrictions. I'm like, sorry. But then it was really neat. They brought out all these, you know, so not only are they doing this tasting menu that changes every day based on what

ingredients they have. They're also like modifying it for us. I don't know. I thought they did a great job. Luckily, I was still hungry when they served the fish because the, you know, I've never done a tasting menu before, so I didn't know it follows like a certain flow and the fish comes at a certain time, which is earlier than the meat. So, sorry about that. So I was hungry. I was still hungry enough by the time the fish came. What was your favorite?

The fish, the tuna. It was. They did the tuna steaks. That was really good. Yeah. The octopus was fantastic, too. Although I don't like eating octopus, like sort of when I think about it, especially after seeing that movie about them.

But it was so yummy. Anyway, for those wondering, so the dish that I love so much was Rabbit, and I was surprised at how incredibly good that. Now, I've had Rabbit before, but I've never had it as good as this one was. It was really terrific. So that was it for really Malta. We got back to our rooms very late, and we're up probably, well, I was up to like 3am doing things like writing my journal entry. then had to get up at, I don't know, 4.30 or something to go to the airport.

I think Kerry was up even longer than that doing her work. We flew back. We had a positioning flight. We flew economy to Amsterdam, then flew economy from Amsterdam to London, and then premium economy on Virgin Atlantic from London to JFK. I think that so premium economy is is like somewhere between economy and business class it's not like just economy with a little more leg room and I think Kerry didn't really understand that before we got on the plane right I was really impressed I was expecting like exit row economy like I thought like premium economy is when they just stick you in like the nicest economy seat they have or whatever I was really really blown away not knowing that it was going to be that nice made it like almost more exciting to me than the business class flight yeah it was funny because we get on and Kerry's like this is like business class to me you know she's tiny so she can almost lie flat on it but they did a great job I've done a few other premium

economies before but this was way better than deltas or and both were way better than Laftanza's premium economy. But Virgin Atlantic had great service, and the food was all served on like proper plates and glassware and things like that. And the food was very good. And I didn't see what they were serving in business class, but it all seemed like what I would expect in business class, not what I'd expect in economy. And so, yeah, you know, for a daytime flight, I thought that was really fantastic. Yeah, it was awesome. It was definitely like the whole meal was very comparable to the Air Serbia business class meal that we'd had.

Yeah. So anyway, to some things up, we were able to fly like the longest flights from the U.S. to Europe and then back. The overseas portions were all in premium cabins. So again, live flight business class on the way out. and then a premium economy on the way back. And the vacation involved a lot of, you know, interesting stuff that we did, a lot of interesting stuff we learned about, a lot of sunshine, a little bit of rain, and, you know, fun snorkeling and hiking at that cove.

A little bit of meeting locals, not a lot of. of that. Well, I think it's worth like repeating for anybody who kind of just stumbled into this, that Greg's trip, all of that, right, flights, the hotels, the stuff he did, like everything for Greg was

just 100,000 points and less than $1,000. Right? Well, did you come of like $970? Is that right? $168. Yeah. $968 and 100,000 points, which, I mean, we've seen a few cards that have offered that 100,000 points with like a single card bonus, right? So that's not an out-of-reach

number of points and probably not an out-of-reach amount of cash compared to what most people spend on vacation. Yeah. Yeah. No, that's a good point. I mean, in fact, it has a very high spend requirement, but the business Sapphire Reserve card has that 200,000 point offer, which if you wanted to cash in half of that for $1,000, then you would have the equivalent of my budget for this trip right there. And that's, of course, at the time that we're recording this, that... Yeah, very big change. At the time where we're saying this.

So, the requirement again was at least three nights in a bed, a thousand dollar budget and a hundred thousand point budget. Greg spent 97,000 points. So he came in under budget, spent $968, so came in under budget there too. And he... Then he spent four nights, which was one additional than the required three. But given all the things he talked about here, he gave himself a rating of, did you say B plus, I think? Or was it B plus?

B plus. Yeah. So you rated yourself B plus. So real briefly, to summarize why B plus, although we kind of got a little idea from that summary. Yeah. Okay. So we are going to be scoring the challengers on. Um, we grew on a whole lot of that, a huge number of factors, but we group them into, um, five buckets. Um, one is we called wow. Uh, and that's basically like, uh, things about the destination about, um, you know, what you did on your vacation. Did that wow us? Um, applicability is another one. Like how widely, uh, applicable is what you did to other people. Would people, would others be able to do what you did or something close enough to it so that it makes sense for others?

And that's why, like I talked about, like, why I didn't start in New York on my trip because I want it to be more applicable. The value for your points was another one. And extra bonuses is like kind of a combination of things. But the primary ones are like, did you do this frugally? Did you meet the requirements of staying three nights? Or did you go above that? And you get extra points for going above three nights. And then you have style.

And that's more about the travel. Did you travel in style? And so I graded myself an A-minus for destination. I thought Malta turned out to be a great pick and so I gave myself an A for the location but there were some other components that we look at in that category like adventure. Did you include any activity that was exciting

or pushed yourself out of your comfort zone? And we did stuff that I thought was really fun but I don't there wasn't really anything outside my comfort zone that I did um relaxation is another one uh where I we did bacon time to relax but we didn't do anything special to relax there wasn't like extended you know um hanging out on a on on the beach just for the purpose of relaxing or or going to a spa or anything like that um food I gave myself an A plus for all the reasons we talked about. Anyway, so all these different things, I graded myself, and there were a few things I gave myself A's and some things B's for the destination, but that brought me down to an A minus because

of the couple B's. Applicability, I gave myself an A. That's something I worked really hard on to try to make this a trip that someone could use their points and book something like this. I don't think there was anything I did that would be hard to replicate as far as the outline of the trip that now there were there were details that you might not be able to replicate like for example we got into certain airport lounges because my delta elite status so you might not be able to get into those specific lounges but actually flying that you know the flights we flew and staying in the hotel we stayed at you could certainly replicate if you had the points I gave myself a B for value so even though I came in within budget and everything I was a little

disappointed when I looked at the sum of all the cash like like if I had paid cash for everything what would it come to and I thought it would be I don't know at least seven thousand dollars but it was more like I can't remember exactly but four thousand four thousand something yeah so anyway so it wasn't as high as I thought it would be same thing with frugality like I thought I would spend a lot less than a thousand dollars not thirty two dollars is less than $1,000. That might be a lot.

I didn't rate myself highly on those things. Let's see. So I'm just going to briefly look at my other one, see if there's anything worth talking about before we go in. But the point is... While Greg looks at those, I want to mention... You mentioned, because you're talking about applicability and the Air Serbia business class came to mind

because a reader emailed earlier today that was looking for a specific trip for next summer and said they couldn't find any business class availability. And I used a word tool. to do a search for the month they were looking at next summer. And I found two seats or more on Air Serbia and business class, like almost daily out of Chicago, not quite daily, but a lot of days out of Chicago and New York. So if that's something that you saw in Greg's trip and appealed to you, there seems to be

quite a bit of availability on the Air Serbia. That's a great point. So Air Serbia is not like, it's not the swankiest business class you could do, but it was good. I mean, it was like on par with what a regular average business class is. You do have the lie flat seats. If you do some studying up about their seat configuration, you can sit in a nice seat with plenty of room. And I say that that way because there are seats with very little room. They're very weirdly laid out.

And I would not hesitate to fly them again if they're going to where I want to go. And it also points out why I chose, why I thought using Air Canada aeroplane miles to book that flight was a good thing for applicability. Because even if you're not flying Air Serbia, I think that Air Canada Airplane has so many partners, including all of Star Alliance, but also lots of other partners, that I think they are the, probably the single best program to find award availability across the Atlantic. That's my assertion anyway. And Air Serbia is a good example because you couldn't book this with United Miles or any other, like, major miles because Air Serbia is not part of Star Alliance. They're an individual partner with Air Canada, and that's why I was able to book it with

aeroplane points. So that was good. I gave myself just a B plus for style. So this is like, did you travel in style? Did you stay in luxury? I thought everything we did was good, but nothing was like over the top luxury. You know, we weren't flying Q suites. We weren't staying in a park hyatt.

But it was all very nice and comfortable. Yeah, yeah. But now I want to know how the contestants feel. So now that this trip is done, are you shaking in your boots or are you feeling pretty confident? Which parts are you confident about which parts are you not confident? confident about and I want to know where you are because I'm pretty sure Nick you've got a fake background going on and Tim does not have a fake background but has are those palm trees there's that's not your living room and Stephen we never know where you are so okay we're going to start with Nick first tell me how you're what you're confident about then what you're shaking in your boots about and then where you're at okay I I what I'm confident about I'm confident that I'm confident that I I've planned a trip that's going to showcase some enjoyment of fun stuff. And I think that there will be a sense of adventure.

So I think you'll get some of the adventure category from my trip. And I'm just I'm just downright excited about the trip. I think when you plan a really good vacation, you know that excited feeling you get. It's like the anticipation builds up. And I'm actually just excited to do this trip. So that's, I think, where my excitement level is that I think it's going to be a lot of fun. And hopefully readers will find some inspiration in it. And I think there'll be some fun surprises along the way.

I threw some hints in a post that I wrote today and some people threw in some guesses already about things. So I think there'll be some fun twists, hopefully. Anyway, we'll see. What am I? I was shaking my boots on day one because number one, I didn't expect, I mean, I didn't expect Julian on day one, and Greg met up with Julian Kiel, the founder of points path. I thought that was cool, but I wasn't yet shaking in my boots.

Sorry, Julian, until I saw Carrie there too. And then I was like, oh, uh-oh, this is going to be good. And then when they boarded a business class flight to Europe to start out, I thought, uh-oh, it is, it's going to be trouble from here because if they managed to do that, I figured at that point, Greg, would probably be flying premium economy home. And so I didn't know where they were going to go or what they were going to do. But that was already quite a bit of luxury on just 100,000 points. I mean, most people would probably anticipate that would only cover the business class flight or not much more than that. So to cover a business class flight there, a premium

economy back and a few nights in hotels, that did make me a little bit nervous. But, but, you know, we'll see. And then what was the last part I'm supposed to have to shake? You have to. You have to spill the beans. Where are you? Ah, yes. Well, I will spill the beans and say, I'm at home. You're right. It's a fake background, but I'm at home, just not in this particular room, but this room is more attractive looking

than the white wall behind me if I didn't have the fake background. So did you travel to that room in luxury? I walked, yes, all the way here. You know, speaking of walking, I will say that, I have been working out these last couple of weeks because I'm going to need a little bit of core strength and endurance. So I'm, yeah, I've been on the bike every day just about. Got myself up to about nine miles a day.

So there will be no ferries pulling away from me this time. No surprise, 32-mile bike ride for Nick. Right. Are you doing a triathlon while you're away? I'll see. So, yes, I'm still at home. My trip will start. That's as much as I'm going to say.

We'll have to keep an eye on the blog and on Instagram, of course. We haven't mentioned this and we should have by now that I think the best place to watch these things is on Instagram. Of course, we're going to have all the updates on the blog. Also, we'll each be publishing daily journal updates as to where we are and what we're doing and what we think of it and all the rest of that. So for folks who prefer to read, you're not going to be left out. Don't worry. But if you want to kind of feel like you're on the trip and following along with it, Instagram is really the best way to do that because you can check the stories and see things kind of chronologically and look at the reels. please check that out and follow frequent myler on Instagram if you're not already yeah thank you for

that um okay stephen you're next up so again um what are you feeling confident about now that you've seen gregg's benchmark trip um what are you not feeling confident about and where are you okay so i'm feeling like can't answer any of that yeah you're not sure where you are it's just hard to like disclose stuff without disclosing stuff so So I guess I'm excited about my destination and activity or, well, activities, actually, that I have planned. I think that that's going to be something that even if it wouldn't necessarily be people's first choice for their own vacation, it might well be something that they would actually be interested in doing nonetheless. And so I'm hoping that that gives some applicability.

my trip is going to be incredibly replicable, I think. So I'm hoping that that ends up showing through just because I feel like it's something that pretty much even a novice would be able to book themselves if they wanted to, just because I wanted to make it so that people of any level would be able to do that. And let's see, I guess my biggest concern at the moment is actually budget cash-wise. because a couple of my activities are overly cheap. And so I do need to be careful, especially with things like food and drink. I definitely don't want to be cheaping out on stuff.

But I do need to watch my budget just to make sure that I don't end up going over, which I imagine Nick's, like, I can see Nick's little grin there, because I'm the most few one and I'm normally the one who like stays well under budget and has like a whole ton of money left. At the moment, I'm like, well, if I can stay below Greg's $968, I'll be doing well. So I'm confident I won't go over $1,000, but I would like to stay under $968 if I can just to be able to spend less than Greg. But it could be touching go. If I have to go over $9.68 up all the way up to like $999 and $99, then so be it.

I'll make you feel better, Stephen. I'm going to push the pedal to the metal. I'm going to leave no dollar left behind. I might be able to the chance of earning some bonus points for spending the least out of everyone, potentially, but I'm not overly confident about that. In terms of where I am at the moment, I am in New York City. So actually flew back over here several days ago with my wife. We met up with her parents up here in New York, so we spent a few days with them. And I'm happy enough to disclose that I'm going to be leaving tomorrow.

Okay. And you partially picked New York to make it more applicable to our readers, right? Yes. So, yeah. You don't live there anymore. You don't live in the States anymore. Yeah. So I'm based in the UK now. And so that didn't seem like it was going to be like a fair comparison, A to Nick and Tim, but also for readers, like because very few frequent reader are going to be starting a 100K vacation from the UK. So I figured, okay, I'll come back to the U.S., start from there, and then go off on my trip. So, yes, I'm in New York City. All right. Cool. All right, Tim, so what are you confident about?

Which category are you confident about? Which one has you shaking in your boots? And what do we see behind you? Where are you? So in terms of which category has me shaking in my boots, it's the flying guests. in to share my vacation with me category. Bjorn is available. You should do my...

No, Bjorn is not available because he was like, no, I need a vacation after my vacation. Like, I can't do that stuff back to back. But yeah, I mean, you know, Greg did a great job of just having all these fun surprise guests. It felt like an episode of like a late-night variety show. I mean, like, here's the name. next guest. We're going to do a bunch of fun games with the guest, right? And

spoiler alert, I, well, we'll see. I still, I'm going to, I'm trying to get Bono, but he hasn't responded yet. But I don't want to raise expectations. He never responds to my messages either. Oh, really? Geez, I was hoping. I was hoping maybe he just was busy. Gosh darn it. Okay. Um, yeah, you know, I don't, you know, it's funny. I don't even, um, it's hard to say even confident and not. I mean, like I said, I, like I, I, I, Bano is not going to show up on my trip. But I had a fairly, with these challenges, I always tend to get kind of, I'm, I'm like, what is kind of the essence of this challenge? And how do I do a trip that to me feels like the essence of this challenge and, and full disclosure, I read your grading post today.

Me too. So, so like, I don't. And it's like, and I, because I almost, I don't want to even let that affect me. And so I purposely put it off because I just want to create a trip that I think kind of shows what I think the, like the heart of the challenge is. And so I kind of gave myself some different parameters. And I don't think they're necessarily like exclusive parameters. They're within what, what you guys set up, but just different parameters where I wanted it to feel like somebody has a week off. What's a vacation look like for that person? And then when my trip's done, I want to feel like this looks like a vacation that somebody might have taken. I wanted to, as opposed to hunting a place that is offers good value, I wanted to show good value

at an expensive and popular place that people would go. So I limited myself to the 15 most expensive countries that Americans go to. And I want to, in terms of the applicability, And I actually kind of misunderstood it a little bit, but that's beside the point. The applicability thing, like, I thought that was a great idea. And so for this trip, like, I set myself a goal of not using any elite status, no hotel instruments, no card link benefits, nothing. There's nothing about my trip that a person who has read Frequent Miler of the last year could not replicate. And so those were kind of my big three in terms of what I was doing. I feel pretty confident about that.

Now, do I feel pretty confident that that's going to, like, beat, you know, Stephen riding sharks off the coast of Madagascar or Nick skydiving from, you know, wherever he's going to skydive from her? You know, I have no idea. I have zero confidence that I'm going to win, but I have confidence, but I feel really good. about what's here in terms of like the parameters that I was looking for. Do you know that you just revealed? I didn't actually, I didn't actually answer the question. Yeah, but Tim, do you know that, do you know that you just reveal that you're not going to be riding sharks or skydiving?

Unless you're being very cheeky. Yeah. Maybe that's exactly what he is doing. Oh, that would be tricky. Well, now Nick's going to change his trip and go do that. I know. I know. I'm going to throw Bono out there so that when Ozzy Osbourne shows up from the dead, it's going to be so much more exciting. But yeah, so anyway, all that to say, I don't even, like, I don't even know what confidence feels like outside of that.

So I guess that those are the parameters that I would use for it. I have, I have zero confidence that I am going to be chosen as the winner over Nick and Stephen. Hmm. Zero. Okay. But I do think I'm going to have a pretty cool trip. So I think that, and to me, that's, that's more the, that's more the fun part of it. All right. And where are you? Well, I'm in what's commonly known as Pepperland. The pizza place in Malta?

The old, the old folks call it the United Kingdom. Oh. Tell us about that. When did you, when did you actually depart? So are you an Epcot or something or? No, no. I'm actually in the United Kingdom and a little, a little place they call Marlebone. Is it, did I say that right, Stephen?

Marlibone. It's not Marlbone. So, like, marrow bone, but Maribon, Merlebone, like that. Is there a L? Or, kind of like the L and the E are sort of silence, so it's not about our land, but

Maribone. Maribone. Maribone. This is like Qatar all over again. This is what I find out that I can say I'm going to get my entire life. I'm going to get my local interaction going around asking people to pronounce a Merlebone for me. So, okay, so you're already overseas.

Tell us about that. When did you start? So I started, like Stephen, and again, I sort of had a different take on applicability. I looked for the area that has the highest volume of North American travelers leaving from and decided to depart from that area, which was the New York metro area. more passengers depart through that area than they do through any other area in the United States. And I really wanted to, like I said, maximize this whole time. And so, and I don't want to get into a full trip report now. We can do that later. But, and I have always, I, I got to say,

and this is, I don't, I don't, nothing, no offense, East Coasters. I hate East Coast. Europe flights. I hate them. I hate them. I hate them. I hate them. Too short. Yes. Exactly. They're too freaking short. They're like it's the exact same reason why I don't fly red eyes from the West Coast to the East Coast because they're five and a half hours long. By the time you have dinner, there's three hours left. I can't sleep for the crap anyway. I agree. It's a waste of fly business class, isn't it? Right. Right. It's like it's useless. It's so useless. Like you can't. And then like you go overnight. You get there at seven o'clock in the morning. And, I'm bleary-eyed, I'm jet-lagged, and all these sort of things. And so I'd always said, I'd always thought, what would, what would it be like to, to like, I don't fly red eyes from the East Coast or from the West Coast to the East Coast? What about taking a daytime flight to Europe? There's only a handful of them. And so right at the beginning of this challenge, I was like, on October 1st, I want to take a daytime flight to Europe.

And that's what I did. And I got to say, it's freaking awesome. And you built your time. I left New York at 8 o'clock. I got into London at 7.30. We very nearly ended up on that same flight. I don't feel blue. I think Stephen might be on that same flight tomorrow.

Actually, I'm curious. I'll be places you out. But yeah, like, it's just, it's, it really is. It's awesome. I would, if I was flying from the East Coast and this is going to be controversial to a lot of these coasters, I would take a daytime flight over business class any day of the week. I just think it's a way nicer way to show up in Europe for me. And now that said, I can't sleep worth of crap, like in anything but a prone position, like a flat position.

And even then it's tough. So, you know, take out of a grain of salt. But it's so good. Quick question for you, Tim. Answer, just as yes or no. Are you on the terrace I think you're on? Oh, yeah, yeah, yeah, yeah. So we have a few more details about this terrace that Tim is on.

He's been secretly sending me footage all day, but we didn't want people to know where Tim was until after this live. So make sure to watch Instagram to see more about this terrace that Tim is on. Oh, cool. That's exciting. Yeah. So I won't, yeah, and I don't want to give away, like I said, I don't want to make a full trip report or give it away like everything about what's been going on.

We need to create a healthy degree of mystery. But yes, all that to say, the cathedral, I don't know if you can see the cathedral spire in the back. Little shadow. It might fade in and out. But yeah, that's in Pepperland in the posh neighborhood of Marlebone. Marlislebone. Maribon. Maribone.

Maribon. Maribon. Maribon. Maribon. I place to Y L.E. That's her. Oh, man. So anyone else feeling nervous?

And Nick and Stephen, how do you feel about the fact that Tim's already hit the ground running? Make you nervous at all? It makes me a little nervous in that it means that he could potentially fit in like seven nights of accommodation into this challenge if he has enough points for that. And so that would be pretty impressive if he manages to do that. So it makes me a little bit nervous that he's going to do that because that would be. obviously be more than either nickel I will have been able to achieve just because we have to be done

October 8th so but you're in a you're in a lodging tonight Steven I am in New York but it's not part of the challenge so oh okay sorry separate yeah yeah I feel I think it's pretty funny that I had a very similar perspective

to Tim I think on different in many ways but similar in that I wrote a post that I published today where I said I decided that for a while I was focusing on how can I get like a wow factor in terms of value for how much I got, how many flights or, you know, the expensive hotels I booked. And like there's going to be some wow factor, but I realized I was focusing so much on that and less on the vacation that I was building a trip instead of a vacation. That's what I said. And so then I pulled back and I said,

okay, well, you know, how, what would I do if I could spend a week doing whatever I want to do? And, you know, Greg's trip was, I think, a really great example of a lot of us really enjoy that group environment, the family trip, hanging out with friends. And, and that is great. But there's also sometimes compromises when you do that. I know. I mean, I travel with kids all the time. We got to make compromises about where we can go and what we can do and whatever else. So I said, you know what? If I got a solo vacation, what would I want to, what would that trip look like? What would I want to do? And so I, I think it's cool that like Tim and I both had at least Tim and I maybe Stephen too had that perspective of okay well what would a really fun trip look like to me. I'm a little nervous that my applicability

won't be as good as Tim's and I don't know as good as Stevens or not because I don't feel like I have as much of a handle on what Stephen's doing yet from what you said there. But I hope any way that what I do looks like a vacation that you could say, okay, well that was a vacation. You definitely had a vacation whether or not that's going to be what everybody else wants to do. And I think that that's kind of cool that we share that perspective on it. So hopefully, hopefully we're going to get that. I'm a little nervous though, like Steven said, that he did get the head start today. I did for a while when I was looking at some of the territories I had talked about potentially booking. And I was looking at a position to London to start. I had that exact flight

on my radar for quite a while. And then it went up in price. And I said, somebody booked it. And that was you, Tim. Maybe thank you, because I'm pretty excited about the trip that I ended up with. So maybe thank you for both. You're welcome. I'm seeing what you do. Although, it would have been pretty fun. I got to say, I was half expecting either you or Stephen.

And once I knew that Stephen was attending a daily show taping today, I knew Stephen wasn't going to be there. But I was half expecting to see one of you guys at the gate. It's like, oh, that would have to change the designments. That would have been like the Million Mile Man of stuff where we kept showing up the same places. Right. I had actually considered like trying to leave today before and I'd looked into my options for that. And I do have it in my points budget to book another hotel somewhere if I wanted. Only thing is that with like two sets of activities that I'm doing,

I need to do them on specific days. And so I couldn't, I just couldn't make it work based on when those are going to work. And so I was just like, okay, I'll stick with the number of days that I'd, God, so it would have been nice to have gotten an extra one, but yeah, I had to make do with what I had. Yeah. So question for Tim. So first, a statement, which is, you know, when I've done daytime flights, when I recently

did a daytime flight to London, the great thing about it is you have to get up really early East Coast time. So, you know, then you fly during the day. And by the time you get to London, you're going to be tired at sort of a normal time. You could go to bed at 11 and actually fall asleep, even though East Coast time, it's only like 6 p.m. and West Coast time. It's even earlier. I agree with everything you said. But you had to stay up. You had to stay up. Now it's my 3 a.m. for you? Is that right? It's 3 a.m.

Did you get a good nap in or anything? Oh, no. Oh, no. No, no. I spent some time exploring the town. And, you know, and honestly, it was, yeah. But I will say. and I don't want to, to your point, I completely agree with it. And I was just talking to my wife before this. And I said, you know, this, it would, it would be awesome because I'm ready to go to sleep. You know? Right. I'm ready to go to sleep at like 11, 12 o'clock.

Yeah. Right. It's such a perfect way to battle jet lag because you don't, you don't have it. You just go to bed at normal local time when you arrive, yeah. Man, I love it. I'm a concrete. They're going to start increasing the price on those awards. Well, and there's not, what I think is really interesting. and not to go on a tangent, but just a small tangent.

What I think is really bizarre is it's such a great experience. Like, it would be like if 90% of the flights from the west coast to the east coast of the United States were at night. And that's how they run transatlantic. And it's like there's, I mean, you really have to search. There's only a handful of these daytime routes. And it's like, why don't, and they're all heavily booked because everybody wants to use them, you know. Yeah. I think the reason is that, um,

And, you know, the other thing is almost all of them fly to London, almost all of the daytime flights. And I think the reason is that most other European airports, they want to have the flights arrive at a time where they can have a connection where people can connect to another flight to get to their ultimate destination. And morning flights just won't work for that because they arrive at night in their destination. And I think London is often enough the final destination for people that that's why it works for flights to London is what I suspect. Yeah. Yeah, I'm surprised we don't see some of that to Paris, though. Yeah. Like Barcelona, Madrid, like some of these other Western.

It would be nice. If you're listening airlines, it would be nice. I think part of it as well is that a lot of cities, they don't allow flights to land after a certain time as well. And so they're kind of limited as to how late in the morning. the flights can depart from the US in order to make it to those airports on time just in case there's like a delay of an hour or two or something like because if it's due to I feel like London might have a cut off of like 10pm or something like that I might be wrong on that but it means that if you're due to arrive at 730 if your flights three hours late it's

just not going to be allowed to land there so I think there's that risk element involved for airlines with deciding to do those kind of flights too that would make for some good content though for Instagram if one of you guys is on a flight that's not allowed to land. As long as you have good internet on your flight. Nick? It should be really good. I think we'll take just a few questions. We don't have a lot of challenge-related questions. So we'll start with this one for Greg. Redemption on V.S., which is Virgin for some reason, right? V.S. Why? Yeah, good job. Redemption Virgin in Europe is distance-based, not considering layovers, something you advocated. Is it worth the extra time to save some miles due to layovers in Amsterdam or Charles de Gaul, which

you did? Is it worth it? Would you do that if it weren't for the challenge, for instance? Well, I think what they're referring to is a different trick. So you can fly with Virgin Atlantic. Like, you could fly, for example, Air France from, I'm going to make up an example. I don't know if this is exactly right, from like Venice to Rome for as low as few as 4,000 points, but it's flying through Paris to do that. And so because Virgin only calculates a distance from your starting point and your ending point when you're flying Air France or KLM within or near Europe. So it includes Northern Africa, too, that you could do this.

And so if the distance is below, I can't remember if it's something like 600 miles, somewhere in that range anyway, then it can be as cheap as 4,000 or 4,500 points, something to do that. Is it worth, so the question is, is it worth going way out of your? way, well, depending on what two cities you're doing, you could be going way out of your way to get to Paris and then to go back to very close to where you started. I would say, I don't know, I wouldn't do that except for as one of these challenges. Or if I could find, if I wanted to do something in Paris, or you could also do this with Amsterdam, if you could get the KLM flights to line up. If I wanted to do something in Paris or Amsterdam, and I could go. And I could

get and I can arrange it so that the flight arrives in Paris or Amsterdam like one afternoon and the next flight back is in the morning, then you could have like a, you know, a night in one of those towns or sometimes you might be able to do a day. Like maybe you arrive early in the morning and you can spend the day there and then do the next flight in the evening. All right. How did you end up in business class in Serbia? I never heard of it before. Never even heard of it before. Yeah. It was simple as I used award tool to search for flights and that option came up right away as something bookable with Air Canada Aeroplane. And so I went to Air Canada and verified that it was able to book that. So I, you know, I looked at a few reviews of their business

class to make sure it wasn't horrible and their views were good enough. And so, yeah, it was pretty easy, actually. All right. Shows right up on air Canada.com also. So it's an easy to book partners. There's no, you don't have to call anybody or anything. It's just right there on the Air Canada website. And you heard us talk about Greg doing all this for under 100K. I don't know if he mentioned when he recapped his trip that it was a 20% transfer bonus from Chase to Air Canada era plan that made that doable because it was it's 70,000 miles for what or 70,000 aeroplane points, I guess it is, uh, for the, the flight he took, but it only cost him 59,000 chase ultimate rewards points. Also keep in mind that if you've got an ultimate rewards card and the chase aeroplane

card, you always get a 10% bonus and that can stack on top of the 20% bonus to get you even a little bit more value for your points. Right. Yeah. That's a good note. This person asks quite relevant. Did any of your vacations take advantage of mile transfer bonuses? So without sharing too much, too many specifics, did anyone else take advantage of mileage bonuses? Do we do a show of hands? Show of hands. Yep. That's everybody's. Everybody did. I mean, that's a superpower. Did anyone do more than one program? So I did both Virgin Atlantic transfer bonus and Air Canada Air Plan. So two people did more than one. Did anyone do more than two trans two different programs yeah so some people have the of having multiple transfer bonuses are like a superpower right because it makes it helps you

expand your budget and and get more points out of your points and tim had a whole bunch of transfer bonuses so you know actually within the last six months yeah and and and again I actually only did two I didn't do three I was just I kept raising oh yeah no no I only Yeah. Another question for Greg, Greg and I, I guess. How was the breakfast at the Hyatt Centric Malta? Did they have local food? Yeah, I thought it was good. They did have local food. There wasn't, or at least we didn't see a menu you can order from, but there was like a, you know, an omelet bar, omelette station where you could get things made to order there. Yeah. What did you think, Carrie? Yeah, I thought it was really good. And I did really like the local.

the local food. Most of it was stuff that we recognized by the time we had done all these kind of food. Yeah, but yeah, we'd be like, oh yeah, this is the thing Berena talked about where this is the one thing he didn't bring us and we'd see it on the thing and be able to try it. They actually had a pretty good selection of both local foods and kind of standard Western foods. Yeah.

And then we'll make this the last question for you, Greg. somebody says, was there anything you would do differently? I mean, they have a longer question, but that's the piece that we'll take time to answer right now. Is there anything I'd do differently? You know what? I mean, there's nothing really that stands out as something that like, oh, I wish I had done this other thing.

It all worked really well. Let me modify it then. If you were to go back to Malta, what are the things that you would do differently? like, you know, if you weren't constrained by this artificial budget, what would you do differently? Yeah, thank you. That's right. I would absolutely stay in Valletta instead

of St. Julian's is the main thing that I would do differently. I probably, even though it was really fun, if it was just my own vacation, I probably wouldn't fly out random friends. Random. That's take offense. As you should, Kerry. As you should.

And I would do, I probably would do, some of those things that tourists do, but I would look for a, like a boat tour, either a private boat tour or one that's a very small, small group tour to go to the different islands and do, there's like kayaking trips you could do on the islands. And so there's a bunch of, there's actually a lot still to do in Malta that I didn't get to, which is always true. of every vacation I've ever taken. So there's nothing special about that.

But so I guess you could say, you know, if I do anything differently, I would stay longer and do more, more of the things before I left. Yeah. All right. I think we'll let Tim go to bed. Oh, no. Come on. Actually, no, no, maybe we should go late.

Maybe we should do another few hours. Yeah, for sure. So he misses his next. I want to make sure he doesn't miss breakfast. Let's keep him up. Yeah. Make sure to check out the Instagram. for the most immediate updates on what these guys are doing.

I think one of you, yes, Stephen already revealed that he'll be leaving tomorrow, and Tim's already gone, so you know that there will be content, so make sure to check that out. We'll also upload it to YouTube as we're able. And thanks for joining us, everyone. Our next live check-in is, I can't even remember. Saturday, October 4th. 6 p.m. Eastern time.

Saturday, October 4th, 6 p.m. Eastern Time. Come back for the midstream check-in where we'll find out where everyone is. We'll do a little tallying of how their budgets are doing so far. Yeah, so make sure to check that out. Thanks for coming, everyone. And we'll see you on Saturday, I hope. Hi, I'm David Brody, co-host of the Travelin'10 podcast.

Together, myself and my co-host, Tim Johnson, have traveled to over 150 countries around the world and all seven continents. Now we're sharing our favorite places, some of our best tips and experiences from all around the world in just 10 minutes on Travelin'10. Join us atvoyescape.com. I'm Pauline Fromer.

I've spent most of my life writing, talking, and thinking about travel, not just where to go, but how to go in a way that's meaningful. On the Frommers Travel Show, we explore the trends, people, and ideas shaping how we see the world. If you care about the why, as much as the where, I hope you'll join me. You can find new episodes weekly at voyescape.com.