Finding Cheap Flights to Anywhere in the World with Scott Keyes
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I'm your host, Chris Hutchins, and I'm on my own quest to find every hack there is. And today, I want to learn everything I can about getting the cheapest flights. So today, I'm talking to Scott Kyes of Scott's Cheap Flights, an email service he founded in 2013 that now has over 2 million members and helps them find incredible deals on flights every single day.

He's also the author of the bestselling book, Take More Vacations, a guide to search better, book cheaper, and travel the world.

In our conversation, we'll walk through finding and booking the cheapest flights, how to travel more and be happier, what you need to do exactly when your flight gets canceled or delayed, and Scott will share his Greek island trip, which doesn't just work for Greece, but can save you over $1,000 on international trips. So let's jump in. Well, after I play this obligatory reminder.

Chris Hutchins works at Wealthfront. All opinions expressed by Chris and his guests are solely their own opinions and do not reflect the opinion of Wealthfront. This podcast is for informational purposes only and should not be relied upon for investment decisions. Scott, thank you for being on the show. Thank you so much for having me. Great to be with you, Chris.

Yeah. And thanks for writing the book. I just read the book. So I actually binge read the book over the last two or three days. And it's fantastic. Well, listen, you're catching me not 12 hours after I got news that it hit the national bestseller list. So if I seem like I've got a little bit of a glow about me today, if there's a little pep in my voice, that's why.

Wow. So now we upgrade the podcast. We're now talking to a national bestselling author. I got to make sure we fix that in the intro. I need to upgrade my self-image, too. You know, I just got no, no, I get to say I'm national bestseller. Look, it feels something that's like I never could have imagined that this would happen. So the amount of just gratitude for folks who went out and got the book and are excited to read it is endless on my part.

Well, congratulations. I think travel is one of the most incredible things you can do with your time. So I love that you're helping make it easier. How did you get into all of this?

It was very, very serendipitous. I was not one of those folks who always knew they wanted to be an entrepreneur, not one of the folks who was like, oh, I definitely want to have a startup when I grow up and just looking for that million dollar idea. I was the exact opposite. I never thought about getting into entrepreneurialism.

I was a journalist. I was a political journalist based in D.C. and somebody who did not have much money in his bank account, but still wanted to be able to travel. Like I wanted to be able to go over to Europe and go over to Asia and Africa. And I knew that folks out there somehow were getting cheap flights. But every time I would look and every time I would search,

it seemed like those flights were really expensive. Like they were, you know, I mean, just ungodly sums of money that made international travel, frankly, out of the question for me until I started to really kind of immerse myself in this, you know, really kind of put on my journalist hat. Why are flights so volatile in price? Like, why is it that this, you know, flight will be expensive today and then cheap tomorrow and then really expensive the next day?

I just threw myself into this world and it all culminated in 2013 when I got the best deal that I've ever gotten in my life, which was nonstop from New York City to Milan for 130 bucks round trip. Wow. The funny thing about that

flight was that I woke up that morning with zero intention of searching for flights to Milan, of booking a trip to Milan. But when I stumbled across that deal, I mean, gosh, there's basically nowhere in the world I wouldn't go for 130 bucks round trip. Right. And so I

took this trip, had an amazing time, you know, and skiing in the Alps and went hiking in Cinque Terre and went to an AC Milan match. It was awesome. When I got back from this trip, all my friends and coworkers kept coming up to me, "Hey, Scott,

I heard about that great deal you got. Hey, listen, next time you get a deal like that, can you let me know so I can get in on it too? And so rather than trying to remember every single person I was supposed to let know next time I found a deal, I was like, why don't I just start a simple little email list? And this way I can let everybody know at once. And that's how Scott's Cheap Flights began. But it was just, you know, for the first

Two years, it was just a hobby, just something I did for the love of the game until at one point in 2015, it had grown large enough. Friends are telling friends, people were signing up. They had grown large enough that this hobby of mine graduated out of the free tier of MailChimp. And all of a sudden they started asking me for 50 bucks a month.

to send emails about cheap flight alerts to my friends. And so I was like, "Ah, I don't want to pay MailChimp 50 bucks just to do this thing I used to do." But then it also dawned on me, "Wow, there's a real hunger for this thing. There's a real demand for cheap flights, surprise. And I wonder if there's a business opportunity here." And so that in 2015 is when I first started exploring how do I turn this into an actual company.

And how many people work at Scott's Cheap Flights now? Right now, there's close to 40 people on the team, which is, again, as somebody who never intended to start a company or become an entrepreneur, is totally surreal. Completely bizarre. Is that mostly people researching deals to try to create content for...

your emails? It's not, you know, we've got our flight search team is about six folks. And then the rest of the team are, you know, people doing member success, folks doing marketing, folks doing building the product and engineering and design all this, you know, run the gamut of different parts of the company. But the folks doing those flight searches and really kind of

keeping their eyes, that radar going for whenever cheap flights pop up. I mean, that's the real core of things because they are doing just yayo person's work every single day to make sure that when those great deals do pop up, we don't miss them and our members don't miss them. Yeah. So...

So I read the book and it dawned on me, right? Your mission is take more vacations. Why do you think people aren't taking more vacations? Yeah, so this was the central question that kind of prompted my curiosity to write this book.

Most of us, when you look at survey data and you ask folks, most of us say that we want to travel way more than we actually do. You know, not only go up and ask somebody, would you like to take another vacation? Absolutely. But you see it in New Year's resolution data. One of the top things every single year, I want to travel more. When you ask older folks,

What do you wish you had done? What are your regrets? What do you wish you had done more when you were younger? It's almost always travel more, see more of the world. And so I said, well, we all have this real hunger to travel and take more trips. What is it that's stopping us? And so I figured, look, there are two main things, time and money. I can't give you more time, but I think it's a little bit overrated the extent to which a lack of time is curtailing our vacation ability because

When you look into the data of how people use their vacation time, assuming you do have a job that gives you paid time off,

Most people are not using their full allotment of vacation time. Over 50% of people leave vacation days unused every single year. You know, collectively, we leave about a billion days of vacation unused every single year as Americans. It's not for lack of time. I think it's the headache and expense and uncertainty of booking flights that's stopping us from traveling more. You know, the mental experiment that I like to propose is,

Imagine you could snap your fingers tomorrow and all flights anywhere in the world were just 200 bucks round trip.

where would you go? How many trips would you take? I think for most people, they would go to Brazil, they'd go to Spain, they'd go to Japan, they'd go to Australia, they'd go to Botswana, like all these amazing places around the world. And I think we would take far more trips than we actually do right now. I think people will be taking three or four or five vacations, whereas right now they might be taking just one every single year. And so it dawned on me,

If you can master cheap flights, and if you can all of a sudden get over that hurdle, learn how to not overpay for flights, but learn how to really take advantage of the cheap flights that are all around us, then you're able to take more vacations. You're able to take better vacations, happier vacations, and you wind up enjoying yourself more, not only on the trip, but when you get back as well. And so this book was this culmination of me realizing, okay,

Folks, I wanted to kind of convey not only how to find cheap flights, but the myriad ways in which they are truly life-changing and how they can really change the way you travel and the way that you go through life and be able to avoid that situation where you grow up, get old in life, and look back and wish you had traveled more when you were younger. That's what I'm trying to give folks the ticket and permission to do now. Yeah.

Yeah. I mean, I've traveled. I'm trying to take a trip every year overseas at least once a year and small trips around the country or North America shorter. I know that one of the coolest things, my sister went to college and I had learned a while ago that only like 50% of Americans have a passport. And I just recently saw last month, another survey said only 37% of Americans have a valid passport. And I thought, well, that's a huge barrier. And the coolest thing about the school she went to was everything.

they had a fund. Someone made a lot of money and donated a fund to the school to give everyone a passport. So when you went to college, if you didn't have a passport, some wealthy man or woman or family or endowment decided we're going to donate enough money so that every kid has the ability to travel internationally and

when they graduate. And so I'm a huge fan of that. I thought that was so cool. I love that because not only is it such an incredible world out there, I mean, yeah, certainly within our own country, but outside it too. I mean, there's so many amazing life-changing places, but travel, you know, one of the chapters of devoting is this fact that travel is medicine.

It leads to happier trips, more of them. Folks who travel see huge boosts not only to their own personal well-being, they're healthier, they're happier, they're more professionally successful, they're more likely to get promoted at work. All of these things that really kind of give us a boost in our well-being just by being the type of person who is taking those trips, who's going to Europe and South America and Latin America. And far be it from the

situation that existed decades ago where travel was something that only existed for the rich and the wealthy. We are living right now in the golden age of cheap flights. It has never been cheaper to travel overseas as it is right now. And so I want to make sure that folks know the good news. This is why I'm out here preaching the gospel of cheap flights, because if you realize

I don't have to pay $1,000 to fly to Europe. I don't have to pay $1,000 to fly to Asia. I can get those flights sometimes for as little as, you know, just a couple weeks ago, we saw flights from the U.S. to Japan for March of next year, for March of 2022, for $202 round trip from all over the U.S. And so if you can put yourself in a position to get those flights,

I used to pay more to fly home to visit my folks in Dayton, Ohio, than I would have paid to fly to Japan for this trip. And Japan is amazing. If you have not been to Japan, anyone, it is one of the most amazing travel experiences you can have. I often get asked, where's your favorite place to travel, Scott? And I hate picking because it's like picking between your children, but...

If I'm forced to, it's always Japan and Mexico, like those two places in my mind. If I can only go to two other countries outside the U.S., it'll be those two.

Yeah, I have. Japan's always at the top of my list. If you have a time machine or, you know, to go forward or backwards, Syria was was a top country for me. Yeah. I'm not saying Syria is a great place to go right now. But 10 years ago, we went and it was incredible. And I'm optimistic that sometime in the future will be another great travel. So that must have been like just before the war. Yeah.

It was unintentionally... It was in 2010. Wow. Like, really? The year before? That's amazing. Yeah. But wonderful country, amazing people, so hospitable. Yeah. So...

Okay, so $200, is that a target? If you told someone, if you really want to get serious and you want to travel overseas, should they be waiting for $200 fares? Is there a sweet spot where you think like, this is kind of what you should expect if you're kind of flexible?

Yeah. So the way that I would think about it is that you have three main areas of flexibility. And the more... You don't have to be fully flexible to be able to get cheap flights. Cheap flights are not something reserved for, you know, 22-year-olds who have no obligations whatsoever.

whatsoever. Cheap flights are there for all of us, but the more flexibility you can give yourself, the better your odds of getting a good deal. So there are three main areas of flexibility. There's where you travel, there's when you travel, and there's when you book your flights. And so even if you say, okay, I really want to go to Japan,

If you can give yourself a lot more flexibility in those other two areas, say, I want to go to Japan, but it doesn't matter when I go. I'll go whenever the cheap flights pop up and I'll book when they, you know, when those flights do pop up rather than saying, I have to book my flight this week or I have to book my flight next week. That's how you put yourself in a good position because when those $202 Japan flights popped up a few weeks ago, there was no way of knowing in advance that those deals were going to pop up.

We had nothing, you know, there was nothing in the literature. There's nothing in the historical data. There's no way to say definitively, this is where that next cheap flight is going to pop up. I can guarantee you they will pop up. You know, I've been doing this job for six years and every single day we see cheap flights pop up. But where that next one will be and when it'll be available for, it's...

impossible to say in advance. So the more flexibility you can give yourself in certain areas, the better your odds of still getting a good deal. Even if you don't have to say, I'll go, you know, anywhere, anytime you can say, I want to go to Japan. I'll keep my dates open. I want to travel somewhere over the summer because maybe I've got kids in school or I've got, you know, I'm a teacher. This is the only time I can travel, but I'll keep my destination open because that way I'm still giving myself the best odds of getting a

a cheap flight, thinking of flexibility less as a binary, less as an on-off switch, and more as a dimmer switch is going to be how you put yourself in a good position to get those great deals. And if someone said, okay, I want to go to Japan, is this the kind of thing where a cheap flight to Japan, maybe not all the way to $200, but let's say not $1,000, maybe $400, $500, $600, $600,

Do you think they have to wait on average a week, a month, a year, two years? How often do kind of the average destinations show up on the really good deals? Yeah, great question. It depends. It depends a lot on where you're flying and where you're flying out of. So if you are in a big city, you know, New York, L.A., Chicago, San Francisco, they definitely get the highest quantity of

One of the things I actually argue in the book is that small airports like my home airport growing up of Dayton, Ohio, actually get the best deals because the normal price of flying, let's say somewhere like Dayton to Tokyo, normally they're $2,000 or something more. But in that deal, in that Japan deal a few weeks ago, there were flights available from Dayton, Ohio to Tokyo, Japan for 233 bucks round trip.

And, you know, that's a far better deal than even the $202 roundtrip flight from New York to Tokyo, because New York to Tokyo is a fare that you would normally expect to pay a lot less for, maybe in normal time, you know, $800, $900. And so that $700 drop, it's excellent, don't get me wrong, but it's nowhere near the, you know, $1,700 drop like you saw with the Dayton flights. But so flights to Japan,

They've actually been popping up a little bit more often lately than they have historically. Obviously, you can't go to Japan today, and we don't know exactly when it'll reopen for tourism. But the good news is that most of those flights have availability all the way through March 2022. And so if you book it now for...

10 months from now, I think, A, there's a very high likelihood that things will be open by then. And B, even if they're not, the airlines are giving flexibility now so that when you make a new booking, you can change your dates without any penalty to do so. You can, you know, it used to cost $500, $600, $700 to change your dates. And now you can just do so without any penalty. If the new dates you switch to are more expensive, you have to pay the fare difference. But if the new dates are cheaper, you actually get the difference back

in the form of a travel credit. So all the more reason to be prioritizing cheap flights. But how frequently cheap flights pop up depends a bit on the destination. We see it almost every day to Europe and especially Western and Southern Europe, almost every, you know, certainly every week to like the Caribbean and Latin America, where you see it

A little bit less common is parts of Southern South America, most of Africa, Oceania, Australia, New Zealand. It's not that deals never pop up there. They certainly still do, maybe once every month or two. But

Because there's just less flights between the U.S. and those places that there's less competition that tends to drive the availability of cheap flights in the way we see to like Europe and domestic travel and Hawaii and Japan and places like that.

But it sounds like if I had a goal to go to New Zealand sometime and I could book it anytime in the next 12 months and I'm paying attention, I could probably find a deal once a year. Oh, 100%. I mean, if you put yourself in a position by giving yourself that much lead time, you say, I'm going to monitor over these next 12 months and get a good, you know, and be patient when the flights are expensive, but pull the trigger when flights are cheap.

there's basically nowhere in the world that you can't be able, that you wouldn't be able to visit and get a cheap flight doing so. Now, you know, not all cheap flights are going to be equal. You're, you know, we regularly see flights from, let's say, basically all over the US to Barcelona for like,

300 bucks round trip, you're not going to very often see a $300 flight from the US to New Zealand or the US to the Maldives. But when the normal price from the US to New Zealand is $1,500, you can count on finding that deal some point over the next 12 months for 700 bucks.

600 bucks, sometimes maybe even 500 if we get really lucky. By giving yourself that much leeway, you're putting yourself in a really good position. The analogy I like to draw is there's this saying among pilots that altitude is your friend. If there's a problem with the plane, if there's something wrong with the engine, you'd rather be at 30,000 feet than at 3,000 feet because you have a lot more time to fix it and just a lot more options.

If you're hoping to get a cheap flight, altitude is your friend. You're going to have a lot better opportunity to find that cheap flight if you start looking 12 months in advance than if you start looking a month in advance. Okay. So in the true flexible sense, that makes sense.

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- Anything to do other than just sign up for Scott's Cheap Flights and wait? Are there other places you should be looking, other things you should do to get these cheap flights? - Absolutely, absolutely. But look, Scott's Cheap Flights is there to try to make sure that you never miss when great deals pop up out of your home airport. But it's still, you know, a lot of folks really love

searching for flights, really love poking around, seeing what's out there. And the amount, like the number of tools out there to help with that these days is like, man, I wish these tools existed like 10 years ago when I first started traveling. So my, I was using ITA matrix back in the day. Yeah. Yeah. Bizarre code lines. Oh gosh. It pains me now to think about it in retrospect. But what are the tools? What's the toolkit?

for a person who wants to be a cheap flight hacker and find all the deals. Absolutely. So the first and foremost, Google Flights. Google Flights is one that, like the hidden secret to know here with when you're searching for flights is that the price is,

is going to be basically the same no matter where you search. There's nowhere that always has the cheapest flights. It's just not, despite all the millions of dollars in marketing and this and that, whether you search for your flights on Priceline or Expedia or Direct with the Airline or Google Flights, it's all going to generally be about the same. And so the way that

I tend to decide where I want to do my flight searching is which one has the best user experience. Like which one has, well, lets me search the quickest, most powerful, I can look at all my options. And to my mind, it's Google Flights. So, and the reason why I like Google Flights, lightning fast, you can search not just one airport to one destination, you can search seven origin airports to seven destination airports.

and it'll show you the single best fare among any of those routes. And so let me give you an example of how that's useful. Let's say you live in Philadelphia. You want to travel to Europe this summer. You don't care exactly where you go, and you know as soon as you get to Europe, you can hop on a train, you can hop on a Ryanair flight wherever and get your final destination really cheap. You just want to get a good deal flying across the ocean. If you go to kayak, you'll have to search

you know, Philadelphia to Berlin, Philadelphia to Dublin, Philadelphia to Paris, Philadelphia to Rome. And each time, you know, it's going to take 20, 30 seconds. Like with Google flights, you get to search, not only put in Philadelphia, but you get to search all three New York airports and all three DC airports. And you can say, you can put in seven different,

or seven different destination airports in Europe say, okay, I'll check for flights to Paris, Amsterdam, Brussels, London, you know, I don't know, Barcelona, Madrid, and Zurich. And of everything

all 49 of those possible routes, what Google Flights will do is it'll show you the single cheapest one across any dates over the next 12 months. And so this way, it makes it really simple to be able to quickly isolate what is the cheap flight that's available rather than having to do 49 separate searches the way you'd have to do on some other flight search engines. So that amount of flexibility and really being able to see quick

what are the cheapest options is how a cheap flight lover like myself and like I hope I'm trying to convert many folks into that's the way you're going to get a really good deal. Yeah. And I also I use Google Flights almost exclusively. I like to you know, you can say up

Up to two-stop, up to one-stop, depending on where you're coming from. You could say total travel time. I think when you start getting into long international itineraries, sometimes you might see these crazy 14-hour layover plus two changes. So not only can you use that calendar to look at dates, but if you set those rules, they refresh the entire calendar. So that when you're looking, what is it like in June? What is it like in July? They're filtering all that for dates.

only flights that are less than 30 hours, which if you were flying from New York to LA would be crazy. But if you were flying to Japan from Florida, it might make more sense. Exactly. And that's such a key thing that a lot of folks, when they first hear me ramble on about cheap flights, what they might be thinking in their head or what they might be saying to me is,

oh, these cheap flights, they must be terrible flights, right? Like it's all on Spirit. It's always like five stops and 40 hours of travel. No, no, no. Cheap flights do not have to be inconvenient flights. You know, today's expensive flight might be tomorrow's cheap flight. Those $202 round trip flights to Japan on a five-star airline with one stop on route. You know, that $130 flight that I got to Milan was a nonstop flight on United with $202.

to check bags included. Cheap flights can absolutely be great flights. And if you kind of tell yourself, oh, if it's going to be cheap, then it's going to be terrible. That's a recipe for ending up getting really expensive flights because if you resign yourself to only thinking expensive flights are out there, then you're not going to hold out for them being cheap. It's not the way hotels are where the price tends to reflect the quality.

Price in a lot of ways on a flight is a completely independent variable to how good the flight is. And so there's a game you mentioned in the book, which was when you sit down next to someone, ask them, hey, how much did you pay for this seat?

and you could be sitting in virtually the exact same seats. Let's assume no one's in the middle. So you're in aisle and window. Someone could pay five times as much as you did for your flight. If you have 100 people on a flight, chances are they paid 100 different prices to be there, or at least like 98 different prices. We think of, you know, a lot of folks get, I think,

stuck in this category error of thinking of airfare as something that is static and stable or thinking that they're, you know, I'll get asked, what does it cost to fly to London? What does it cost to fly to Tokyo or Miami or Hawaii? There is no one price. You know, like the, my favorite

fair that I can remember to illustrate this was a flight we were looking at from Atlanta to Amsterdam that on Monday was $800 round trip, on Tuesday was $300 round trip, and on Wednesday was $1,300 round trip. And it was the exact

same flight. And so, you know, rainbows and gold coins to you if you booked on Tuesday and got that $300 flight and, you know, just like thunderstorms and woe to you if you booked on Wednesday and paid four times the price. Yeah. And

And you mentioned these don't have to be on budget airlines. How do you feel about budget airlines? I have my only story for budget airlines, which is a spirit story, was we went to Cartagena, Colombia for my bachelor party and...

Spirit decided while we were at the airport that they weren't going to fly to Columbia anymore. Not just that day, but we called customer service as soon as we saw this line not moving. And they were like, sorry, we don't fly to Columbia anymore. And I was like, what do you mean you don't fly to Columbia? You're just not going... So we all, every single person had to buy a new flight or wait three or four days until Spirit would book you on... Their systems were not fast. Right.

That's like maybe the worst case scenario, but is there a place in cheap travel for these budget airlines? So your story exactly illustrates the way that I think about budget carriers. I love budget carriers, but I basically never fly them. And the reason why I love them is because

It is thanks to the Spirit Airlines of the world and the Norwegian Airlines of the world and the AirAsias that we are living in the golden age of cheap flights. And the reason why is that competition between airlines is the number one determinant of cheap flights. And so when Spirit comes in and says, oh, you know, American, you're charging $500 to fly down to Columbia. What happens if we come in on

for those flights for 200 bucks. Most people are going to book that Spirit flight because when you look at survey data, by far the number one variable, the number one determinant that people are using to decide what flight to book is just price. It's a commodity. They're not saying, oh, I really like American, so I'm going to pay $300 extra. We're just like, this is just a means of getting from point A to point B, so I want to go with what's cheapest. And so this is why I love budget airlines

Because by setting that $200 price, they're forcing the other airlines, your Americans and your Deltas and your Air Frances, to drop their prices to compete. You know, when Delta first rolled out basic economy fares about a decade ago, the original name for them on investor calls was Spirit Match Fares because this was their way of trying to compete with them. But why? So, okay.

Scott, you love them so much. Why do you never fly them? Well, for exactly the reason that that sort of nightmare scenario that you ran into. If something goes wrong, if a flight gets majorly delayed or canceled on a budget airline, that has the potential of really upending your entire trip. And what I mean by that is,

If you had been booked on, let's say, American Airlines down to Cartagena, well, even if American, even if that flight that you had been on got canceled, well, they fly down to Cartagena four, five, six, seven times a day. They'll put you on a different flight, let's say, or they'll put you on a partner airline in the region you get to fly on. Now you can fly on JetBlue down or anybody else that they're partnered with, whereas the budget airlines,

They tend to, A, have very sparse schedules. So maybe they're only flying a couple times a week to Cartagena. B, they tend to not have partner airlines. And so when that flight gets canceled, even if they had still continued been flying to Colombia, it might have been three days until their next flight.

flight there. And so all of a sudden, what am I supposed to do? Just cut three days off of my trip, off my vacation? Yeah, stay at the hotel airport that they're putting you up in for $25 a night. Horrible. And then even if then you're in that worst case scenario of you get the refund from Spirit, I got to imagine those last minute, when you're booking those last minute same day fares on another airline, those must have been incredibly expensive. Those must have been a horrendous price. And so

The potential for those really bad situations, like when something goes bad on a budget airline on your itinerary, it can go really bad. Whereas the downside risk with the full service airlines tends to be quite a bit better. You know, something goes bad, your flight gets canceled. Usually it's only going to result in a few hours delay to your getting to your final destination than you would have otherwise. Yeah.

And when, you know, so totally agree. I think if you're thinking about, oh, I want to take a quick, quick trip somewhere. And if it if there's a problem, it's not a big deal. And I've got lots of flexibility, maybe it's fine. Or if you live in a hub city for an airline, that's a budget airline, maybe it's fine. But I agree.

I will not be flying budget airlines in the future in these kind of international scenarios that aren't country hubs, because that was just a disaster. Yeah, absolutely. You know, each trip is going to depend a little bit. And to be clear, like,

A, I think the actual onboard experience of most budget airlines is basically the same as, you know, if you're flying American, you're flying United. I don't think it's going to be that drastically different. And B, oftentimes, actually, budget airlines have more direct flights depending on where you're flying than many of the legacy airlines that do a more hub and spoke model. So you always have to connect, you know, American through Charlotte or through Miami or whatever. You might have more direct flights on the budget. But

you know, seeing how often they're flying, if it's one of those things where it's international, it's twice a week. And so if my flight gets canceled, I am really screwed here. Those are considerations that I'm taking into account when I'm trying to decide which flight to book. And so, you know, look, if that Spirit Airlines flight is $800 cheaper than American flight, yeah, I'm going to book Spirit. But if it's

$50 cheaper, $25 cheaper. To me, it's generally worth the premium to pay to be flying on a full service airline. Yep. And we talked a lot about flight gets delayed, flight gets canceled. What are your tricks when that happens? You're at the airport and you've just learned your flight is canceled. What do you do that makes you better off than other people standing in line or waiting around? Oh man, I like, I jump into like,

hyper organized. This is like Scott at his peak superhero mode. The flight gets canceled. Okay. First thing I do is I go find, you know, where the customer service airline is and I go stand in it because I want to make sure that I'm getting as good a spot as possible. And in case, in case my problem can only be solved by in-person agent, but generally speaking,

folks, phone agents for the airline have just as much power as the people in person at the airport. And so while I'm walking to that line, while I'm finding that customer service place and reserving my space in line, I'm calling up the airline and trying to get my ticket rerouted, trying to get a new flight directly with somebody over the phone, because that actually might end up

being a lot quicker, especially if the line is long or there's no wait over the phone. If I'm calling the main service line and they're saying an hour wait, two hours wait, three hours wait, what I'm doing, not sitting there waiting for that. What I'm doing is I'm looking up then what are the international

phone numbers for this airline. So Delta doesn't just have, you know, offices in Atlanta for you to call. They've got offices in Canada and in Mexico and in the United Kingdom and Singapore and all over the world. And so, you know, you want to check what your own cell phone rates and policies are about international calls, but nobody really thinks to call Delta's Canada office

But the Canadian agents for Delta can help sort out your itinerary just the same as an American agent could. Without the whole time. Yeah, exactly. And, you know, nobody else is calling them. So you generally are able to get right through. So those are the types of things that I'm doing quickly. I'm also looking up and seeing what are my best alternative options. You know, I'm pulling up Google Flights. I'm seeing on this airline or any partner airlines, what other...

What ways can I get to my final destination right now? Irrespective of the price, take whatever fare it shows and just totally ignore it because when your flight gets canceled or delayed or something, the airline just wants, they still have to get you to your final destination. They're not charging you anything to put you on a different flight. So just find out what flights look most convenient for me, what's best for my schedule.

Because if you can come in prepared to that agent, hey, yes, you know, my flight just got canceled. Can you put me on that next flight that goes, you know, through JFK and then over to Rome? They are much able to help you more quickly. I mean, look, they've got hundreds of people they're trying to take care of. You're always going to be your own best advocate. So the more information, the more preparation you can do before you get somebody on to help you, the better off you're going to be.

And then I think you probably said this in the book too, but it's something I've been doing. If something goes wrong...

I wouldn't demand it, but I would ask if there's anything you get for that, right? If the best flight's tomorrow morning, do you have a hotel? Do you have a meal voucher? Can I get food? If there's no seats in coach, can I have a seat in business class? Even if there are seats in coach, can I still get a business class upgrade? You know, they might, they're less likely to do it when it's a, you know, I don't know, it's canceled for weather, thunderstorm, something like that. Then if it's a sit, but if it's a situation where let's say your flight is oversold,

and they need a volunteer, not only can you expect to get a voucher for some amount of compensation, you should hold out for as much as possible, but you should absolutely be asking for those things. Think of it like the secret menu at In-N-Out where they're not going to tell you, oh, you can negotiate for a business class seat on the replacement flight you're given. You can negotiate for a hotel room for tonight or this or that.

But if, you know, especially if the airline's in a desperate situation, you can 100% ask for those things. Worst case, they say no, but best case, you're going to get it. And I've gotten upgraded to business class on flights that I've been bumped off of because, again, when the airline is in that situation, oftentimes they don't have a lot of leverage because especially, I mean, you remember the David Dow incident on United. I mean, United lost everything.

tons and tons of money because of just the PR hit from dragging this poor guy off the plane. Whereas if they had just then, hey, we'll give you a first class seat, we'll give you a thousand dollar voucher for your next flight. Like you even if you didn't get him to agree to it, somebody on that plane is absolutely going to take it. And so remembering the leverage that you might have, it's always worth asking.

Yeah. And I actually go in and look whenever I'm taking a flight where I'm flexible. I look how full it is. I've remembered a couple times where I'm, you know, let's say I'm in the bathroom and then I hear them announcing like the flight might be sold if you want to do something, come to the desk. I'm like, no, I want to go. So if a flight is full, look at the seat map. If you're flexible and you take a voucher, definitely go to that desk and say, hey, I'm

I'm flexible if you need anyone. So you're first in line because if you wait until they make the announcement, you might be fifth in line or 10th in line. - Yeah, it's very much a first come first serve environment where oftentimes even if I think that situation might exist, if I've got some flexibility, I'm hoping to get a decent voucher.

I'll sometimes just pick the seat that's closest to the gate agent's desk because I know if I'm that first one in line, I'm going to get the voucher rather than somebody else. Yeah. All right. So I want to just jump through a bunch. There are a bunch of travel hacks, both that I have that you put in the book that are all around flights.

But first, when do you book the flight? Is there a point in time where you're waiting when there's no flexibility, right? I have a family reunion. Yeah, we're supposed to go. And it's over the 4th of July. It's, you know, right now fares are expensive. I've looked all the airports I can drive to all the airports nearby. There's just nothing cheap. You know, what do you do when there's not

You know, do I wait to the last minute? Do I just buy whatever it is three weeks out? How do you decide what to do when there's not flexibility? Yeah. So first, let me bust two myths around when is cheapest to book. There's still the sense that a lot of people have that flights are cheapest to book on Tuesday at 1 p.m.

I don't know if you've ever heard that one, or sometimes they'll say Saturday at midnight or some arbitrary time. This was true 20 years ago when airlines first started selling their tickets online because they would actually just load their fares on once a week. And so if you were one of the first ones to book right after those fares got loaded, you might be able to get one of the only handful of cheap seats that they had available.

The problem is that that hasn't been the way that airlines have been pricing their tickets for years. Nowadays, tickets are set in airfare set algorithmically, you know, it's set by these fancy big computers that are much more dynamic, right?

And airfare is changing every single day, oftentimes by the hour, if not by the minute. And so rather than it being a preset time like it used to be, there is no single cheapest time or no predictable cheapest time when flights are going to be cheapest to book. No, like set time of the week. Similar with last minute flights, you know, 40 years ago, you often could get a good deal if you waited to last minute because the air, you know, the thinking was, oh, the airline, you

If any seat that is unfilled on that plane, as soon as the door closes, it's just lost potential revenue. So they're going to want to slash the price leading up to departure to try to fill as many seats as possible. That used to be how the airlines did it again 40-something years ago. But now what the airlines have realized is that the people booking those last-minute flights weren't leisure travelers. It was actually tending to be business travelers. And business travelers, not only did they make their plans late,

But they didn't care what the price cost because it was their company paying, not them. And so rather than slashing the price, the way the airlines could make the most money was by jacking up the price and gouging them for those last minute flights that business travelers love to buy.

So instead, you've got a trip rather than waiting for the last minute or just saying, I'm going to book it on Tuesday at 1 p.m., both of which are going to do nothing to help you get a cheap flight. The best way to think about timing of booking your flights is to think in terms of what I call the Goldilocks windows. So not too early.

Not too late, just right in the middle. And if you're traveling, so the Goldilocks windows vary if you're traveling domestically or internationally. If you're traveling domestically, typically about one to three months before travel is when cheap flights are most likely to pop up. For international travel, it's more like two to eight months in advance is when those cheap flights are most likely to pop up.

If you're traveling during a peak travel period, so like middle of summer, Christmas, New Year's, or I don't know, going to Dublin for St. Patrick's Day, you typically want to add a couple months to those recommendations because, again, they're just such popular times that the cheap seats are liable to sell out even sooner.

But thinking about those Goldilocks windows as when cheap flights are most likely to pop up, that's how you put yourself in a good position to make sure that you are getting it when those cheap flights do pop up. Yeah. And I'll put the Goldilocks rules and everything we talk about in the show notes at allthehacks.com. They're also in the book.

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You can only go from the... Like, only Ryanair. Great, low-cost airline, all three. They don't fly to the U.S. You're never going to book a ticket from the U.S. that includes a Ryanair flight. I don't want to say never, but you're saying you can't right now. Yeah. So today you cannot. And...

So my process was, let's find a fare to cross an ocean and then let's find a fare to get where I want to go. You've kind of have a term for it. This is the Greek island trip. Yeah. How does someone execute this well? Yes, absolutely. So...

Let's say you want to travel to Santorini this summer. Look, you know, Greece open for Americans right now, just beautiful, iconic destination. If you go search for flights, let's say from New York to Santorini for the summer, chances are they're going to be quite expensive. I mean, regularly, you know, $1,500, sometimes more. But instead of giving up that dream of visiting Santorini or the Greek islands, what you should do instead is

check for flights from New York to Athens because flights from New York to Athens regularly pop up for, you know, 400 bucks round trip, 500 bucks round trip. If you can get that $400 flight from New York to Athens, you can then all of a sudden buy a separate flight from Athens to Santorini for like 50 bucks. Or you can take a ferry for 50 bucks. It is by...

By combining that trip with two separate itineraries, you're able to get the same trip for a quarter of the price that you would have otherwise had to pay. And the reason why is, to your point, when you search from New York to Santorini,

The way that the airlines and the way that the flight search engines want to sell you a ticket is they only sell you a ticket on an airline or its partners. And no airline is currently a partner with Ryanair. So you can't find that cheapest flight from Athens to Santorini. It'll just have to be on a separate partner airline, sometimes the cheapest flight across the ocean.

on that airline might have the most expensive flight from let's say you know athens to santorini and so it ends up being real expensive by by crossing the ocean as cheaply as possible and then adding on a separate transportation to your final destination that's how you execute the greek island trick and that's how you are able to get you know to these really kind of remote iconic places for 70 80 less than you would have had to pay otherwise and plus the best you know best of all

Because it's two separate itineraries, once you get to Athens, you could spend a couple days in Athens if you want before continuing on to the Greek islands. You can take that time, be able to make it a two-for-one vacation in a way that you wouldn't necessarily have been able to if you had just booked one itinerary.

Yeah, but do leave enough time. It is very likely that you will not be able to check your bags all the way through. Yes. So I would say if you're not going to take a day or two off, definitely leave enough time to go grab your bags, which you might have to do anyways for customs reasons. But just know that when you book your flight separately, you know, maybe you're lucky if they happen to be partners that they'll they'll connect your bags, but often not.

The answer is no. That is very key. And I'm glad you brought that up because not only do you need to consider bags, transit time, all that, but there's also the question of, look, on a normal flight, when you have one itinerary, if a delay on your first flight causes you to miss your connection, well, the airline is still responsible for getting you to your final destination. They'll put you on the next flight. They'll put you on a partner airline. But

If you have this flight from New York to Athens and then a separate ticket from Athens to Santorini, the first flight, the first airline has no responsibility for that second flight on a separate airline or your ferry tickets or whatever. And so you want to give yourself enough buffer time, sometimes even as long as a day or two, to make sure that even if there's a delay on your first flight, it won't result in you missing your second flight.

Yeah. And two sites I'll mention that you mentioned in the book for finding out what airports fly everywhere. I think it was flightconnections.com, which I had not heard of. I was actually using Wikipedia as the place I would go. I'd look at an airport and see all the destinations. I went to Flight Connections and I was like,

wow, this would have saved me so much time. So that's a great place to say, if I can get myself to Paris, where can I go from Paris? Yeah, yeah, exactly. So let me give you a personal example. In a few weeks, I've got flights to travel over to Madrid. And until this morning, until we got the good news that Spain will indeed be open by the time we're there, we have been wondering, are we going to have

to fly somewhere else? Are we going to not be allowed in Spain? And so I'd go on flightconnections.com and I would see where can I fly? Where can I get a nonstop flight out of Madrid to elsewhere that, you know, will be open for Americans? So seeing, you know, can I fly to Albania? Can I fly to Greece? Can I fly to Croatia on a nonstop flight? Because, you know, I've kind of figured, look, I've only got a week. We're going to get there. We'll be tired. I don't want to have to take like two or three flights to get to a final destination. Yeah.

Yeah. And you also mentioned Rome to Rio, which I think helps. Maybe it's not a flight. Maybe it's a train. Maybe it's a bus. Maybe it's a, you know, a ferry. Yeah. A lot of options. I used to use this site called seat 61, which was like all about trains. And it was...

I don't know if it's even still maintained, but it was really cool for very remote places. We took a 52 hour train ride from Zambia to Tanzania. How was that? It was fun. Like the train broke down for three hours. We like got out in the middle of nowhere. We went to a village and we just hung out.

And then they like, you know, pulled the horn on the train and we were like, I don't know if that's a one minute warning or a 10 minute warning. So we just sprinted back to the train. See, I love that. Not only do I love that story, but I think that's really emblematic of, I think it's in chapter 11. You know, we talked about

explore this idea of travel and regrets. And oftentimes we have this sort of like anticipatory regret. Oh, I don't want to go to Zambia or Tanzania because I don't necessarily know the language or the customs or will I like the food or what happens if the train that I'm taking breaks down?

When in reality, you know, not only are you going to have a great time, but if something goes awry, if something funny, you know, happens, even if it's kind of like annoying or stressful or not terribly fun in the moment, it's a great story afterwards. And you have some awesome memories that wouldn't, wouldn't have necessarily been quite as, as salient or quite as fun to relay if it had just been a, you know, a normal trip where everything went exactly to plan and you, you know, you didn't take, you didn't grow at all or get any interesting stories because you didn't risk anything. Yeah.

Yeah, I always say leave some time on your trip to just...

explore and do things because you might not know that you want to do them until you get there. And sure, there are some trips like if you want to go on a safari, it might be worth coordinating that before you go. But if you're just landing in Rome, don't plan every day. Leave a lot to chance. We rented a Vespa and rode around. Didn't think to do that before we got there, but it was so much fun. Yeah. And especially now with smartphones, like being able to just, you're not there having to complete

completely be stranded on your own in a country where you don't know anybody and don't know the language. Your ability to be able to find stuff, to be able to find restaurants, to see what's interesting near you, to get directions, it is much, much, much more possible and accessible now. So you're able to kind of

Have that have that ability, have that lifeline while also not like you said, not overscheduling yourself, leave yourself open to serendipity and let yourself be able to kind of enjoy the spontaneity that travel can bring. Yeah. So I want I want to get back to a few of these hacks. I'll ask you a few. I'll share a few travel insurance. Buy it. Don't buy it.

I personally almost never buy it. And the reason why I never buy it is that I'm already insured in ways that people hadn't necessarily realized. So when you buy a flight, if the airline cancels or significantly changes your flight under U.S. law, you're eligible for a cash refund, period. If the airline has a big delay or they mess up

your bags or lose them. They're going to give you some amount of compensation and plus your credit card, whatever credit card you paid for the flight with. Many credit cards automatically carry travel protections on them as long as, again, you use that credit card to buy the flight. And so I always like to be very cognizant of the ways that I'm already automatically protected

And I don't necessarily want to buy something, pay extra to get protection that I already have. Now, I think there are, you know, some like a few types of trips, something like, you know, a big safari where maybe you had to prepay for the safari. And if the flight

you know, got delayed and you missed it, you're not going to be able to get your money back from the Safari itself. Yeah, there are some instances like that when I think insurance can make a lot of sense. But for me personally, I've kind of come to peace with generally not buying it because I'm already protected in a lot of ways.

Yeah. And one thing you mentioned that's actually become a bigger thing now that airlines have changed the rules. So Southwest has always been this great airline. You can book your flight and you can cancel at any time and you can get money back. Or if you booked it with miles, you get your miles back and it's great. And now a lot of airlines give you that flexibility too. So one hack you mentioned is just

If you want to go on a trip, you could book it now and wait and see if a cheaper flare comes up. Absolutely. You know, I mean, it's one of the best, one of the best changes in policy that the airlines made in the past year was to get rid, permanently get rid of those change fees. And so that if when you book a flight, you automatically get flexibility. But one of the things to very much be aware of is that

It only applies if you book in main economy or higher. It does not apply to basic economy. You're still pretty well locked into your dates if you book a basic economy flight. And so it's something to consider when you're seeing what the price difference is between main economy and basic economy. If it's five bucks, if it's 10 bucks, yeah, I'll always buy up to main economy. If it's 100 bucks, 200 bucks, then I'm sort of sitting there trying to kind of take stock and think, how likely am I going to want

to change the dates later? How much do I feel like locked into this trip with the dates that I had already chosen? Yeah. And the add-on hack that I'll share is...

Let's say you're flying an airline that doesn't have that flexibility. Or let's say you ended up buying that basic economy ticket and you decide you're not going on the trip. I always tell people, don't cancel it now. The difference between canceling it the day you don't want to go and the day before you take off is zero. And if any time up until the day you're departing, that flight is changed, canceled, rescheduled, de-canceled.

delayed, you can call the airline and say, hey, I noticed my schedule changed. It's six hours later. I don't want to do the flight anymore. And, you know, I've tried one time I tried in the flight changed three minutes and they were there was no no leeway. But if your flight changes by a few hours or if it

this schedule changes to a different airport or a different day, you can get your money back. Yes. So this is one of the hidden best things. You know, when you get that email, it says, you know, Scott, your flight schedule has changed. Most people's heart was saying, oh God, what a pain. You know, I view that not as a bad thing. View that as an opportunity.

Because not even, not like, yes, certainly if you want your money back, yes, view that as, oh, this is great. Because again, under US law, you're eligible for a cash refund in full when that happens, when there's a significant schedule change. But even if you don't want a refund, even if you still want to take the trip, you want your flights,

When they make those schedule changes, what this means is that you can actually switch to a more convenient flight than you might have originally booked without having to pay any fair difference at all. It doesn't matter if the new flight was, you know, is more expensive. On most airlines, they'll let you switch to, you know, let's say your original flight was a connecting flight.

But now with the schedule change, you'll actually generally be able to switch to a nonstop flight or to a better, you know, flights with better times, even flights with better dates than you'd originally booked. So viewing this as an opportunity to get a much better flight than you originally booked. Yeah. My example was and this was a miles trip. We booked miles to the Seychelles for our honeymoon.

And I got an email that Air France is no longer flying to the Seychelles. And I told my wife and she was like, what are we going to do? I was like, this is good. So he called the airline and we had booked it in business class. And the airline rebooked us in Emirates first class. Please tell me this wasn't the shower in the sky, was it? So it wasn't the shower, but it was the private suites. So you had a door, which actually on our honeymoon, I was like, well...

I'll see you later. Like you have your room on the plane. I have my room on the plane, but you know, it was too many people. The idea of your flight getting canceled or rescheduled is terrible for us. We basically upgraded from a ticket that, I mean,

Emirates first class would have been probably $10,000. Can I ask you this? So generally speaking, I've only flown in like business or first class internationally a couple of times. So I'm like enough to be aware of how swanky it can be, you know, the fly flat seats, the champagne, the whole works, but not enough that it's become like an expectation. Has it changed?

And the reason why I haven't done it in a lot of ways, you know, because I love playing the points and miles game, but the reason why I'm almost hesitant to do it is I'm worried that it's going to

a sort of lifestyle inflation or lifestyle creep where all of a sudden flying in coach to, you know, Paris or, or, or, or wherever is going to feel really arduous. And, and one, has that been the case for you or does it still feel wherever, however you're flying? It's totally fine. No, no, I, it's gotten to be, I played the miles and points game so hard that it became so easy to fly in business. And, you know,

It was much easier when I had a job where I was running a company and I had a lot of expenses that I put on a credit card or I worked for a job where I traveled a lot. I do neither of those things now. So while I have a lot of points today, I don't accumulate a lot more points. So I'm dreading the time in the future where I've exhausted my points and I don't know what I'm going to do. I've gotten too accustomed that I...

Unless it's a short direct flight, you know, I try to use points to upgrade. I've never paid for it. Yeah, yeah, yeah. I've never bought a business class ticket. They're like really expensive. I mean, you know, with the occasional exception, like I'm not sure folks necessarily realize how expensive trans-oceanic business class flights are. I mean, we're talking not like three or four times, not like double the price, like five, six, seven times the price of an economy ticket oftentimes. Oh, yeah.

Yeah, Japan could be $600 in coach and $8,000 in business. Easily. Yeah. And so part of that is like why I've kind of

pump the brakes on trying on like even considering business class you know maybe i don't know maybe who knows maybe ask scott when he's like 50 years old and he's like oh yeah i need a little more comfort in this guy but i've always been like a little a little wary of like giving letting myself drink from that milkshake too often because i'm like worried like oh man now coach flying is going to be terrible

I think that's a wise move and I encourage everyone to follow it. You're just trying to keep all the award availability open for yourself on business class and all the others. Well, I mentioned Miles. I know you don't talk a lot about Miles in the book until the end. And I thought it was... We did a whole episode about credit card points and Miles. And the advice I thought was really salient, which was... It went into a lot more detail. But at its fundamentals, it's...

If you have flexibility and you're an okay flying coach, points and miles, you might not need them to get a good deal. If you want to fly business, you're going to be waiting for years. If your requirement is, I want to go to Japan in business class and I want to spend less than $1,000, I don't know if it'll ever happen. So I loved the takeaway, which was, if you want to fly business class and you want to get a really good deal, miles might give you that leverage because...

The way I kind of describe it is mile or in the dollars game, a business class ticket might be five or 10 times expensive. And in the miles game, it's like two times as expensive. So you get a deal.

But when you're trying to fly in a cheap domestic or a cheap domestic flight, or you're flying in coach to from New York to London, gosh, just the taxes on some of these miles tickets are more than the coach ticket. Absolutely. And not only that, but I think this is one of those incidental byproducts of now living in the golden age of cheap flights since 2015 or so. It's like when I started out in the miles game a decade ago, you just didn't see very many cheap flights.

long haul, you know, intercontinental flights the way you do now that they're being so regular. And so miles, you know, even me, I was flying mostly economy, entirely economy to, you know, Asia, Europe, South America, but miles were still were a great value because the tickets, the cash tickets might've still cost, you know, 800, 900 bucks to fly to Europe. And so if I could

spend just like 50 or 60,000 miles to fly in economy, I felt like, yeah, I'm getting pretty good value here. But now, you know, if that same 60,000 mile ticket you can get for 300 bucks round trip, well, then it's a horrible value on miles. And to your point where the real, I think, is value is

I think in the points and miles game is in more of the premium seats. And I think this is why you see a lot of the airlines starting to move towards devaluation, trying to make the business class and premium products more higher redemption rates because they're recognizing that this might have been a little bit too generous to be sustainable. Now, there's still a lot of sweet spots

around. There's still certainly great ways to get value. But it's been interesting to me to watch miles go from something where I started my career a decade ago as being especially lucrative for however you are flying to now them being, frankly, pretty marginal when you're flying economy and I think being much more of a value if you're flying in premium. Yeah. Yeah. And

You know, you might... I try to tell people, yeah, you might get a better deal on business class using miles, but you're always going to get more flights if you fly in coach. So yes, you could hack your way to get to a cheaper business class ticket to Europe, but you could also just take two trips.

in coach. And so don't forget that the trade-off is even if it's a good deal in business, that doesn't mean that it doesn't cost two or three times as many miles or dollars as it would to take more trips. And one of the things you said in the book was

people are happier who take more trips. Absolutely. And, you know, where like oftentimes those preferences recognize that that can vary a lot with your age, with your what type of trip you're taking. You know, when I was in my 20s, I would go to the ends of the earth to save a couple bucks because I was time rich and I was cash poor.

but now, you know, into my thirties, getting a little bit older, I feel like, you know, I'm much more willing to spend a little bit extra to get a nonstop flight, to spend a little bit extra to have a more comfortable itinerary than, and, and be able to like get home quicker and spend some time with my young daughter. Whereas, you know, when I,

I think back to this, sometimes this flight I took in my 20s to save a few, I think I saved $30 on a flight from Washington, D.C. to Denver. I took the scenic route. I flew Washington, D.C. to New York

to Boston, to Chicago, to LA, out to Denver just to save 30 bucks. Now, the idea of doing that- You got the story. Exactly. I got a great story out of it. It was certainly a fun travel day. Now, the idea of doing that today sounds horrendous because I have a lot more things I'd rather be doing with my time. But back then, it was really important to me to save as much money as possible and recognizing that, look, different people are in different

situations in their lives. For a lot of folks, cheap flights aren't necessarily a vanity. It might be the difference between being able to take a trip or not going at all. You know, if I, if, if when that $130 round trip flight to Milan popped up at that, that it was,

it wasn't as though i was deciding between that or an 850 flight if it was 850 dollars i wasn't going to go but for 130 bucks absolutely i was going to take that trip and that's why prioritizing cheap flights and making them really the centerpiece of your travel means that you're able to take three or four vacations for the same price you used to pay able to to pay for one and you wind up taking more vacations than you would have otherwise

Yeah. I think if there's something that I've evolved from, it's I'm optimizing for my own happiness. So a cheaper flight means more vacations. I think I mentioned to you last time we talked, there's this book called Happy Money. And they always say, pay in advance for things and you can savor it the entire time before you leave. When you're there, you don't have this bill at the end. And so that doesn't mean prepay for the hotel 3 months out, but maybe like a month.

a week before you leave or right when you get to check in, just be like, hey, can we just pay for this hotel right now so that when I check out, there's not a big bill? One of the most fascinating things for me in delving into the research around travel and happiness for this book was running into research about the way that we tend to enjoy our vacations, where we think, you know, historically, we think of vacation as just something you enjoy while you're on the trip itself. But turns out,

That if you look at the studies that have been done on this, the research, we actually enjoy the anticipation of a trip more than we do the trip itself. We say we're happy when we're looking forward to a trip and we're daydreaming about those, you know, those cocktails on the beach and hang out that cafe in Paris and going bungee jumping in New Zealand. We enjoy that.

you know, anticipating that and that excitement about what's coming for it, then we actually are on the trip itself. And we enjoy the memories of doing those things after the fact more than we do the trip itself. And so, you know, we certainly enjoy ourselves when we're on travel, but recognizing just how powerful anticipation and memories are.

And so trying to, rather than booking a last minute flight and robbing yourself of that anticipatory joy, book yourself a flight months in advance and give your today self months to look forward to this flight, to be able to travel plan and daydream and just be excited about something that's coming up. Yeah, here'd be a great hack I just thought of is,

just book your flight three, four months out. And then sometime in the next three, four months, book the next flight. So that even though you might only take two or three trips a year, if you could live in a world where you always have a next trip plan, you can live in that anticipatory period, which, you know, we know is, is happier. Yeah.

This is one of the ways that I think that cheap flights are at their most powerful is that when you're taking, it's not just the money that you save, but the way that when you take three or four trips a year rather than one trip a year because you got a cheap flight rather than overpaying, what happens is that normal travel cycle, you know, when if you're taking one trip a year.

that trip is great. But then when you get back home, I mean, gosh, you remember that feeling of just a hangover of just like, oh, back to real life. I got to get back to work. We both have small daughters. I think when you get home from a flight with kids, I think it's just,

You know, you almost need an extra day. Yeah, exactly. Exactly. But when you're prioritizing cheap flights and you're taking three or four trips a year rather than one, you don't have that same sort of sense like, I get home and my vacation's done and it's going to be 11 months until I travel again. You have that sense...

oh, I'm back home. I get to readjust to life. And it's only three months until my next trip. It's only four months till my next trip. And I'm already back in the cycle where I've gotten, if I haven't already booked that next flight, I'm about to, I'm seeing what great deals pop up.

And I'm getting back on this sort of hamster wheel of getting excited, anticipatory joy, travel planning and all that. So it turns it from a sort of dreaded hangover cycle to one where you're just constantly excited about what's coming up around the corner. Yeah. And so obviously there's joy in the anticipation. You talked a little bit in the book about the peak end rule, which is how to maximize your joy on the trip.

Can you talk a little bit about that? Yeah. So this is this concept in psychology that the way we tend... We talked about how memories of trip, we tend to enjoy those even more than the trip itself, in part because memories are forever. That trip that you took from Zambia to Tanzania, you're only on that train for, what, a couple of days?

But you've gotten to relive that after the fact for years. The way that we tend to remember our vacations are two things about them. One, we tend to remember them how we felt at its peak emotional state. So you went bungee jumping in New Zealand, you went running with the bulls in Pamplona, you ate some just incredible sushi in Japan. You tend to remember the

peak and you tend to remember what you did at the end of the trip, how it kind of wrapped up. And so one of the, I think with that in mind, knowing that human psychology, we tend to remember the peak and the end, give yourself something really fun and, and, and

really exciting to look forward to on that last day. Because if you can end the trip on a high note, you know, you have a wonderful meal plan, you've got a great tour plan to so far, whatever it is for that last day, that'll make your trip, that'll give your future self so many more happy memories to remember about that trip than if you ended the trip on just something, you know, kind of lackadaisical or just something meh.

schedule something really fun and exciting to look forward to as the last day. And that'll give your future self that much more to be happy about in its memories.

Yeah, I talked to my wife last night. I told her this because I was like, we got to make sure on our next trip we plan something for the last day. And I said, do you remember when we went on our honeymoon? We went to the Seychelles in Paris and in Paris we went to a couple nice like Michelin star restaurants and they were not on the last day. They were on a random middle day. And I was like, do you remember those meals? And what she remembered was she was like, well, I remember at one of them you didn't have a sport coat and you had to borrow a sport coat. And I remember the other one, the

The chair was really old and you got a splinter and they treated you as if the splinter was like a broken arm. They brought out gloves and I was like, do you even remember the meal? Because the meal was expensive. Neither one of us could remember anything about the meal except being full. And I was like, gosh, if we had had that meal on our last day, we would have remembered it for years. And so I think that was...

so great. And on my next trip, I am planning, you know, something epic for the last. Yeah, the psychologist who or I think his behavioral economist who termed this idea peak end rule, he even shared a memory about how when he was traveling with his wife in Switzerland, they were scheduled to have one more day, but they had this just really wonderful, you know, great picnic hiking through the Alps.

They just had such a good time that they had the option of adding on another day, but they decided, actually, let's cut our vacation a day short. Like, we wanted to end on this high note rather than kind of ending on a slump and, again, robbing their future selves of that sort of joy of memories of the trip. And so I'm not sure I would necessarily endorse, like, cutting short your vacation if you have a really great day, but at least trying to plan something really fun and nice to look forward to on that last day. Yeah.

Yeah. Any any other travel hacks, tips, whether it's flights or any other aspect of travel that that we didn't touch that people should know about? Oh, boy. Gosh, I could go on all day. One of the so there are a couple of things, too, that I like to kind of bring up as let's go with like kind of more bite sized hacks here. The 24 hour rule.

This is a federal regulation that many folks aren't necessarily familiar with, but that can be really one of the most powerful arrows in your quiver as a traveler.

What the 24-hour rule is, is that when you book a flight, as long as you booked it directly with the airline, as long as it's at least a week out from travel, you automatically, from the moment you hit purchase, are given a 24-hour window when you can cancel that ticket and get a full refund, no questions asked, no penalties, no fees, no nothing.

And so what the 24-hour rule, where that it's like, A, knowing that you have that in case you book a flight and, I don't know, you decide the next day you thought better of it, don't want it, knowing that you can get a full refund. But B, the ways that it can really kind of put you in a prime position to scoop up a cheap flight. So let's say that $202 Japan flight pops up again.

And you're, you know, oh my gosh, that's an amazing fair, really excited. But your significant other is at work and they're in meetings all day. And you're not necessarily going to be able to get in touch with them to, you know, plan out to propose this idea to scope out some dates. What you can do with the 24-hour rule in mind is just go ahead and book meetings.

a week or go ahead and book three different possibilities for trips. Oh, you know, book one trip in March, one trip in April, one trip in May. And then when you're knowing that this deal might not necessarily last very long, it could be gone in a number of hours. And so if you wait to book until they're out back from home from work,

it's probably going to be gone. But if you lock in the price now, what you've done is you've essentially just frozen that price for 24 hours. And you can decide that night when your significant other gets home, hey, do you want to take that? Should we take this $202 flight to Japan? And if so, should we take this one that booked in March or should we take it in April or should we take it in May or should we take all three? By locking in the price, you get to

Keep whichever one you want and you can cancel the others for a, you know, for free and get your money back. And this isn't a refund or this isn't a flight credit. Right. Exactly. This is a full credit, you know, refund on your credit card. And it's not just, you know, a situation like that. Let's say one of the cool things that the airlines do.

do often is when they're cutting flights, cutting fares, they are oftentimes engaged in what's called a fare war. So that happened with those flights to Japan, where initially, I think American Airlines was offering like $500 flights from the U.S. to Japan anytime over the next year. And then United responded with $400 flights. And American responded to United with $350 flights. And United responded with $250 flights. And they just kept

ratcheting down and down until they got to 200 bucks round trip. And so let's say you had initially booked that $500 flight.

Well, if the price drops down, as long as it's within 24 hours, you can just book that new flight at the lower price and cancel your old flight and get your full money back. And so this is a way, again, knowing within the 24 hours is if the fare drops, if it's a direct flight rather than connecting, any type of better flight, you can take advantage of it within those 24 hours.

Tell me if this is possible. Let's say I want to book this flight and I'm not sure it's not a special deal. I'm just going on a trip. I need to go. I book a flight 24 hours later. Fares the same. Could I just every day rebook the flight and cancel the other one and just keep going and basically have unlimited window to cancel until, of course, the fare goes up and then I stop? Yeah.

- That is a really good question. So here's the way that I would be thinking about that. One, you're gonna have to float the... As much as I wish they were, refunds are not instantaneous.

you know, it's going to be sometimes the airlines, you know, it can be weeks until that actual refund shows up in your credit card. So each day you do it, you might have to be adding another, you know, $200 onto your credit card bill. And so recognizing that it might be a little bit until you get that refund. The other thing too, is that the airlines do have language in their contract of carriage that sort of precludes what they would consider, you know, like essentially gaming the system, whether like, uh,

I, to me, this doesn't seem like game. This isn't, this seems like doing, you know, do it like just putting yourself in a good position, but I could see the airline being like, ah, you know, this is Scott keeps doing this booking flights, canceling them every single day. He's not the type of customer we want. Like airlines are allowed discretion to say like, you're not allowed to buy flights with us anymore. So,

I could see it. I would like to see somebody kind of execute it in practice before I gave a ringing endorsement. But at a bare minimum, anytime you book a flight, 23 hours later, if that flight is cheaper, you should rebook your flight. You should absolutely. And to be clear, the way to execute this is to book the new flight first and

and then cancel the old flight. Because what you don't want to do is cancel your old flight and then book a new flight. But by the time you've canceled the old one, book the new one. I mean, remembering airfare changes sometimes by the hour, if not by the minute. And so the worst case scenario is you've already canceled the good deal. You go to book the new one, but the

the price suddenly jumped and you're all of a sudden left with no flights. Whereas, you know, if you book the new flight at the lower fare, you go to cancel the old one and just, you know, the worst case scenario is you just got outside of that 24 hour window. But even in that situation, you can just cancel the second flight that you booked and be no worse for the wear. So yeah, making sure you kind of go in the proper order of steps here.

I can't remember which airline, but there's at least one airline that if you book that second flight and you put in your frequent flyer number, they say, no, you already have a flight on a seat on that flight. But the hack is just book the second flight with no frequent flyer numbers and cancel the first flight. Go back and add your number to the site. Yeah, I like that a lot because you can always add in your frequent flyer number later. You can always add in your TSA pre-check number later. You don't have to do it right when you book.

Yeah, this is great. I feel like we have a ton of hacks. The other hack that I read in the book that I loved was if you're going to look for a flight for a family, right? You have three or four people. Sometimes you search for a flight for four and you realize, wow, when I was just looking for one, it was cheaper. There are times where it can be helpful to have your itinerary all booked together. But sometimes there might be three seats at a cheap price and the fourth seat is really expensive. And when you try to book all four, you're going to

pay the four, the expensive price four times. So definitely play around with searching for one passenger and then four, and it could be cheaper to book two or three people at one fare instead. That's exactly right. You know, I did that on a recent flight from Portland to New York, where I was traveling, buying three tickets. When I searched for one ticket, actually, when I searched for two tickets, it was $117. But when I searched for three tickets,

it was 177. And so by buying two tickets at the 117 price and then buying the third ticket at 177, I was able to save 120 bucks off of what I would have otherwise paid. Now, the reason why is, again, like you said, airlines want to, when you book multiple tickets on a single itinerary, they want to put it

all in the same fare bucket. So in my case, they only had two tickets left at that $117 price. So if I wanted to buy three, they had to all be at the $177 price. But what does it matter? You're still in the same seats like we talked about earlier. You ask the person sitting next to you what they paid, probably a very different fare. This is a good example of why that can be the case.

Yeah, this is great. Scott, I feel like we covered a lot. I really appreciate you being on here and helping everyone take more vacations, get better deals on flights. Everyone here should check out scottscheapflights.com. I get the newsletter. It's been fantastic. Check out the book. Where else can people find out more? You can all find us on social media, Twitter, Instagram, Facebook, and now TikTok.

Wow. There better be a video of Scott dancing on TikTok. Only if we get to a million followers. That's the incentive. Okay. Okay. Well, thank you so much for being here. Thank you so much, Chris. It was my pleasure.

Wow. I don't think I could be more excited to take another vacation. I hope you are too. And thank you so much for listening to this episode. If you want to get in touch to share your favorite hacks, suggest a topic for a future episode or anything else, Chris at allthehacks.com or at Hutchins on Twitter. Finally, if you're enjoying the show, you can help out by sharing all the hacks with your friends or family. Thank you so much and talk to you next week.