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I’m of two minds when it comes to the world of free travel. On the one hand we can travel for free if we have the miles or points. And free is hard to beat. On the other hand, it takes a lot of time to build up the miles, mileage award tickets aren’t always available, and it seems like a lot of work. That’s why Scott Keyes got my attention.

He and his girlfriend recently took a two-month trip around the world virtually for free. All of the flights–21 of them–were paid with miles. And 95% of their hotel stays were also free. So I invited Scott to the Dough Roller Money Podcast show for an interview. He tells us exactly how he did it, and how you can, too.

Resources Mentioned in the Interview

Transcript of Scott Keyes Interview

Rob: Scott, welcome to the show.

Scott: Thank you for having me.

Rob: I appreciate you taking the time to be with us. I honestly don’t remember how I found you. I was on the internet and just found this guy that said he flies a lot for free. That caught my attention. I saw that you wrote a book so I wanted to bring you on the show to find out how you do it. Why don’t you start by just telling everybody a little bit about who you are?

Scott: Sure. I am a big travel enthusiast as you could have guessed. I just got back from a 2-month world-wide trip with my girlfriend. We took 21 flights around the world and went to 13 different countries, everywhere from the volcanoes of Nicaragua to beer halls in Prague to the Parthenon in Greece and beyond. The interesting thing about this trip is we want to make a point of doing it essentially all for free. Every single one of our flights, 95 percent of our hotel rooms ended up being for free. What let us do a trip like this— We’re not made of money. We’re not billionaires. We wouldn’t be able to afford a dream trip like this. So figuring out these strategies is what enables us to take a trip like this.

Rob: We obviously want to hear how you did that. But how did you get started into this sort-of ‘miles gain’, ‘traveling-for-free’ thing? How did it begin?

Scott: Yes. Slowly but surely. You know, they say “Rome wasn’t built in a day.” This was about 5 years ago. I’d just got out of college with a small piggy bank of miles. I started realizing that I want to make sure I’m getting the most value out of this. I’ve got 50,000 miles in my American Airlines account. I want to make sure that I’m not just wasting it. So I started doing a little research online finding these message boards and forums of other people in this frequent-flyer world who want to try to help you get the most value out of your miles. I started to realize that booking a flight from Washington DC where I was living, back home to Ohio, is probably not going to be the best use of my miles. It would be like 25,000 round trip just to fly from DC to Ohio. But I realized after a little bit of research, for just 5,000 miles more, for 30,000 miles, I can fly from DC all the way to the Galapagos Islands and back. Now that seems like really good value especially considering the ticket would have cost $1,600. So I took my miles, I go ahead and book that flight. Still with that skeptic heart, anticipating that, you know, something can be wrong here. They are going to charge me up ton of fees. There is no way that this will actually pan out. And then when I actually took the flight and made it back home safe and I only spent 30,000 miles and about $45 in taxes and fees, I was a convert. I was a believer. Slowly but surely, I started to look into how I can get more miles? How can I get them quickly and easily? How can I keep taking more free flights like this? And the rest has been history.

Rob: So you said you started with 50,000 miles. Where did those come from?

Scott: Those came just from flying back and forth from college. I grew up in Ohio. My folks are here, but then I went to school out in California. So twice a year, three times max, I was flying to and from California. So in about four years or so, I ended up amassing 50,000 miles which, on the one hand, was a decent chunk of miles. It let me fly for free to the Galapagos and back and still have a lot left over. On the other, what I’ve realized since then is how incredibly difficult it is to amass those miles when you’re actually flying them— you know, you get one mile for every mile you fly and everything— versus amassing those miles from, for instance, credit cards, sign-up bonuses. Where I can just sign up for one credit card from American Airlines and get the same number of miles that it took me four years of flying cross-country two or three times a year to get. It was just very stark in my mind. Wow! I can spend four years flying 15 cross-country flights or I could just sign up for this credit card and get the exact same miles in the end.

Rob: So were the Galapagos Islands amazing?

Scott: One of the best vacations I’ve ever taken. You know, I tell people that that’s the trip where I’ve been most tempted to just take my return ticket and just tear it in half and just set up a new life there. It’s really, really incredible.

Rob: How long were you there?

Scott: About a week I think? It might have been eight days, but we got to go into a couple of different islands. There is some incredible snorkeling there. In addition to all the tropical fish and everything, they have a ton of sea lions that, when as soon as you get into the water, they really do like— I thought it was a farce that they play with you but as soon as you get into the water, they just come swim right up to you and get within about a hair’s breath, then circle around then come back and swim right up to you again. It’s unbelievable.

Rob: Was that a bit unnerving at first?

Scott: A little bit. But you know, they just looked so friendly and fun. And you know, it’s not like a hammerhead shark. It was a great experience.

Rob: Okay, so you have this great experience. You spent some of your miles. So how do you go about that? Maybe you can walk us through your approach to credit cards, if that’s the best and easiest way to build up miles. How do you go about doing it?

Scott: There are a couple pieces of advice that I give to folks. Especially folks who are starting out. Firstly, start out slow. Flying for free is much like any other hobby that you’re not going to become and expert overnight. You need to practice a little bit. You need to do it for yourself and see for yourself that these efforts are worth it. And if you play it right, it’s not a scam. You can actually come out well, well ahead. But, you know, I’m not going to advise people to go out and open up 10 credit cards overnight because if you told me, Scott Keyes, in 2010 that that was a good idea, I would have laughed in your face and said you were crazy. So what I advise folks is find one card that has a really good sign up bonus. Right now, that’s the main thing that I advise people to look at, is just the sign up bonus. Almost every card offers you one mile per dollar spent. Maybe you get two miles if are at an office supplies store, a restaurant or something. Go ahead and ignore all that. Just focus on the sign up bonus. Now, for instance, with American Airlines, they usually have cards that give you 50,000 miles once you sign up and spend some amount of money in the first three months, usually $1,000 or $2,000. Something like that. So just look up at that big sign up. Only go for a card that has a large sign up bonus like 50,000 miles at least. Then just make sure you’re hitting that spending threshold. When you go out to restaurant and when you go out and get groceries, make sure you are always paying through your credit cards so you hit that. And then once you get that 50,000 miles, figure out where is somewhere that you would really like to use them. Maybe taking that dream trip to Rome. Maybe flying down to Brazil. Somewhere where you can use those miles. Once you get back from that trip and realize, “Wow that wasn’t so difficult. I opened up a card. My credit score’s still great. I was able to get the miles and that wasn’t scam miles. I was able to use the miles, so that wasn’t scam. And here I am, a couple of thousand dollars richer for not having paid out of pocket for that flight.” And then start to wrap things up a little bit. Maybe at that point, you are comfortable signing up for a second one. In all things, I recommend moderation and just going slowly so you make sure that you are comfortable with it and not going out of your comfort zone.

Rob: So for the trip to Rome, you mentioned Rome just as one option. How many miles does it take to get free round trip flight to a place like Rome?

Scott: It depends on the carrier. American Airlines, for instance, I just took a flight from the US to Europe. If you are flying outside of the peak travel time to Europe which is between mid-May and mid-October, it is only 40,000 miles round trip from the US to Europe. If you are flying during those peak summer months, which I believe is May 15th to October 15th, you are going to pay 60,000 on round trip. If you split the difference that you fly in the beginning of May and fly home in the end of May, you are going to pay 20,000 to get there and 30,000 to get back. So it will be 50,000 round trip.

Rob: When you focus on the sign up bonuses, I know some cards will give you miles for a specific airline. I guess all the airline have their form of credit card that will give you bonus miles. But then there are cards like Venture One from the Capital One, that I can think of— Barclaycard has one, that are pretty rich rewards and the miles are specific to an airline. You can use the miles to offset any travel charges you want. Are there pros or cons to one versus the other?

Scott: There are also pros and cons. I’ve done once with a Capital One card and they can be useful. The reason why I don’t like them more is the amount of value that you can get out of them is pretty fixed. The way the Capital One card works is they say you get 50,000 miles or something but each mile is worth a penny towards airfare on any flight. So the benefit is you can use that on any flight. There are no black-out dates. There is no capacity control in terms of seats on a plane that are made available as an award. But at the same time, if a flight is really expensive, then it might not even cover. When you need to fly from New York to Los Angeles and it costs $600, even 50,000 miles is not going to cover that whereas with American Airlines, for a round trip domestic flight, it’s only 25,000 miles. It can be good in the sense that you are going to have much more availability but the reason why I tend not to love the Capital One card and other ones like that is because they are essentially a cash-back card that you can only use on traveling. If you are going on that route, you might as well go a cash-back card that gets you 2 percent cash-back in general. And you can use that cash on flights if you want but you can also use it on groceries or movie tickets or anything else. The reason why I like the mileage cards from American or Southwest or whatever is because you play your cards right, you can get really good value out of them. For example, again going back to the Galapagos flight, I just paid 30,000 miles for that. But if I paid out of pocket for that ticket, it would have been $1,600. So that was 30,000 American miles versus 1600 Capital One points. The only other benefit to be aware of the Capital One card is you do get frequent flyer miles for those flights, if that makes a difference to you. Because you are essentially paying with cash, you still get frequent flyer miles for the miles you’ve fly on that flight. Whereas, when I book an award seat with United, I’m paying them miles but I don’t get to accumulate any miles from that flight.

Rob: You alluded to your credit score a few minutes ago. Have you seen your credit score take a hit for all the credit card apps and any kind related to that? Do you monitor your score regularly and how do you do that?

Scott: Actually, I don’t monitor my score. One of the things that surprise me the most of getting into this hobby was I was under the impression that having a number of credit cards is really bad for your credit score. The reason why I was under that impression is because most people who tend to have a lot of credit card are people who are opening up a new one in order to pay off an old one. People are not paying their credit responsibly and people are just trying to stay afloat. The thing that I’ve realized from getting into this hobby are going slow and opening up one card at a time and just following a couple of important rules with my credit and that is always treating a credit card like a debit card and never spending money I don’t have. Always paying off my balance in full at the end of every month and keeping an eye on my credit score. My credit score has gone from decent and fine when I first started out from college to incredibly high. An excellent credit score at this point. The reason why is because every card that I open up when I’m paying off my balance in full each month, I’m showing my credit worthiness. I put charges on the card and then I pay them off each month. I am a credit-worthy customer. I am good at handling it. I don’t have any delinquencies or bankruptcies or anything like that. In addition, one of the main ways in which your credit score is calculated is the amount of charges that you have on your card in the numerator divided by the amount of credit card that you have available to your names. For example, you have one credit card that has $5,000 credit line and you spend $500 in charges there. You are utilizing 10 percent of your credit right there. These are not great, not awful. But if I have 10 cards that each have $5,000 credit line on them but I only have $500 charges at the moment, that is only 1 percent credit utilization. My score is going to be a lot higher. I have ton of credit to my name at this point from all the credit cards but I’m using very little of it. So by opening up all these cards and by using them responsibly but using them frequently and doing this frequent flyer game, I’ve actually really improved my credit score from what it was and made it really tip-top in general. It would be great if in next few years if I’m looking to buy a house or something, I’ll be able to pay a much lower interest rate because I’ve been improving my credit score and it’s been doing well.

Rob: What tool do you use to keep tracking your credit score?

Scott: The two main ones that I like best is creditkarma.com and creditsesame.com. Those both are draw from different reporting agencies but the thing I like about them is they are both free. It is not like that freecreditreport.com or the one that has all the ads. It really doesn’t work out for me. Both creditkarma and creditsesame just monitor your score month-to-month. They’ll send you periodic updates and it will let you know if there are any changes. It will keep an eye on your credit inquiries and stuff. It may do a really good job so those are what I recommend.

Rob: Let’s talk about your two months trip, you and your girlfriend. I think you said 21 flights?

Scott: 21 flights, 13 countries.

Rob: How many miles did the two of you burn on this trip?

Scott: We flew 20,000 miles in the air between all the countries. What we had to pay for this 21 flights per person was about 136,000 miles and that is across a number of different programs. So the most we paid for any one flight was 30,000 miles to fly back from Lithuania to my folks place in Dayton. But the cheapest flight I believe we paid for was 4,500 miles to fly between some Caribbean Islands. It completely varies flight-to-flight. We use a number of different mileage currencies. We use American Airlines miles, United miles, British Airways miles. I think those are the main three. We have a very diversified fund of different miles we were able to use for this trip.

Rob: In the majority of those miles were accumulated through sign up bonuses?

Scott: Yes. 136,000 miles is a lot of miles. But, when you have these programs offering 50,000 miles to sign up for a credit card, in six months or ten months or something, you sign up for three of these, you can do something like this as well. On the one hand, it is not incredibly easy. You have to do the leg work and figure out what is right for you and find the offers and the flights. On the other hand, it is much more attainable than I certainly would have thought before I started this game. I like to say, the proof is in the pudding. I wouldn’t have thought that this is possible and yet here I am.

Rob: How long did it take you and your girlfriend to accumulate those miles?

Scott: Not long. I wish could give you an exact count or figure but the problem is we are just trying to get more airline miles, more hotel points that we can use in the future, so it wasn’t a set start date and end date for this particular trip. That having been said, I think the typical time it will take if you open up three credit cards from first applying to it to then getting the miles and booking the flights, it’s probably a few months.

Rob: Wow.

Scott: Not too long. We first started looking about the planning on this in about December 2014. Then we left to start the voyage in April. So that was about four months in advance. I already had some airline miles and hotel points accumulated but we also made a concerted effort to open up some new ones, do some transferring and look for where we were going to get some good deal and see where we ended up. So yeah, a few months.

Rob: That’s amazing. So for those wanted to try this, do you have one or two or three credit cards that you recommend that have good sign up bonuses?

Scott: Yes. If you’re just looking to fly domestically, the ones that I tend to like the best are either Southwest Airlines— and the reason why I like Southwest, they always have a 50,000 points sign up bonus which is a bare minimum that you want to look for when you are signing up for a credit card. And just as a side for your listeners when you are in the airport and people are hustling you, “Oh, come sign up for a credit card here.” Most of the time, the offer that you will see in the airport is not as good as one that you can get online. Most of the time, Southwest or American or whatever only offer, let’s say 30,000 sign up bonus in the airport. Whereas if you were to go and sit right next to them and pull out your computer and look online, you can probably find the exact same card with a 50,000 points sign up bonus. So, a strong word of caution about signing up in the airport when you are getting hustled by the salesman there. I really like Southwest because they have no fees for bag and because you can change or cancel and it’s like you book without any fees at all. I like it a lot. At times when there’s a flight I might be taking 6 months in the future but I’m not a 100 percent sure, at times I’ll book it with Southwest points and then if I don’t end up taking it or things change, I can change it without any fees makes it really convenient. The other one that I like a lot for domestic flights is British Airways. The reason why is they do a 50,000 points sign up bonus and the way that they do their miles. They don’t have these zones. For instance, with American it costs 25,000 round trip anywhere in the US whether you are flying from New York to Los Angeles or New York to Boston. It’s 25,000 miles round trip. With British Airways, they do a distance base system depending on how much it cost. If you’re flying less than 650 miles, then it’s only 9,000 British Airways points round trip. If you’re flying less than 1100 miles, it’s only 15,000 round trip. So for a lot of these domestic flights, when you are not flying across the country, it can be a really good value. I recommend for folks who are flying internationally, the one that I like the best is American Airlines. We’ve got a 15,000 mile card. And the reason why I like it the best is because they tend to have a really good availability to a lot of place that you want to go whether that is North America or Europe, even Asia. It is also a little bit pricey. It tends to be 65,000 to 70,000 to get there. The other one that I like the best is United. They usually have a 50,000 to 55,000 sign up bonus and you can get really good flights to Europe and to Asia on United. The one that I usually caution people against is Delta. You can get 50,000 miles or 60,000 miles sign up bonus sometimes. The problem is that their miles really don’t have much value. I have probably a 100,000 Delta miles that I just can’t use. I look for flights all the time when I am going to Columbia or even flying to California. They are not always available and if they are available, they charge a ton of miles so they are just not very valuable at all especially compared to the other airlines.

Rob: Most of these cards charge annual fee. Do you eventually cancel the card to avoid the fee? If you do, do you have to wait a certain period of time before signing up to get the sign up bonus again? Or you can’t ever do it again?

Scott: That’s a complex question, I’ll take it piece by piece. I hate annual fees. I really don’t like to pay them so almost every card that I sign up for are cards that waive the annual fee in the first year. And every card that I’ve listed (with the exception of Southwest) waives the annual fee in the first year. It’s really great for me because what I do is sign up for the card— And I keep a little spreadsheet, then I will set myself a calendar reminder for 11 months after I signed up for those cards, to call the bank and tell them, “I’ve really enjoyed having this card. I’ve been a great customer but I noticed that the annual fees are coming up. Can you waive it for me for the next year?” You will be surprised how often that works and that credit card companies see you as a valuable customer. Remember, they are making profit every time that you swipe your card just for swipe fees from the merchants so they have a strong interest for keeping you as a customer. A lot of them are more than happy to waive annual fee for the next year and it happens probably 50 percent of the time. If they don’t, then I will ask them, “Can you downgrade me to no fee version of the card?” A lot of times they will have the card that cost $89 a year or they have one that isn’t quite as good, doesn’t have the same perks but has also no annual fee. About 35 to 45 percent of the time, if they don’t waive the fee, they will be able to downgrade me to a no fee card. And only if they can’t waive the fee and don’t have the downgrade “no fee” card, only then do I tell them “Okay let us go ahead and close the account rather than me having to pay the annual fee the next year.” Some people are really happy to pay annual fees. They think it’s the benefits but there is an argument to be made in some cases. For me personally, I don’t think it’s worth it to pay a hundred dollars to a company when they don’t really tend to offer very mini compelling perks or benefits in order to keep the card open. I almost never pay any annual fee on a credit card. In terms of signing up and being able to get cards multiple times, it varies bank to bank. The good news is it’s still very possible, the bad news is that the banks are clamping down a little bit. For instance, with American Express, it used to be possible to sign up for a card anytime. Say, I sign up for 11-month then I close it. Then a year after that or so, I can sign up again and get the sign up bonus the second time. About a year ago, they just change the rules so that you can only get the sign up bonus once in your lifetime for any particular card. This is something that can only impact people like myself who are pretty intense into this game and wants to get the cards as many times as possible. But who knows if this rule will stay on forever — maybe it could change down the road. But it varies from bank to bank. With Chase, after you had one, you can get a sign up bonus again— Chase does is for the United card. As long as you have not received that sign up bonus in the last 18 or 24 months, then you can sign up and get it the second time. So it varies bank to bank. I usually wait a year and a half or two years between cards but there are so many out there. It’s really easy to create this virtual cycle where you are applying one then in few months applying for a different one. And then by the time it’s been two years, you’ve been ready to try to get the Chase sign up bonus again.

Rob: Do you use any online tools to track all your miles?

Scott: I do. The one that I like best is called Ward Wallet in wardwallet.com. It is nice for few reasons. One is it’s an account manager, password manager, keep all your frequent flyer accounts, all your hotel accounts, not only your account numbers and everything but also your password if you want them to store it. That’s really convenient. The second thing that I like best is that it will keep track of the number of points in each program and they will tell you when those points expire. It’s really handy to keep track of it in case I have a couple of thousand points in my Air France account that I don’t plan on using anytime soon. So, if I’m worried that they might be expiring, then I do something to try to get them not to expire. Maybe I’ll use them for magazine subscription just to make sure I’m getting at least a little value.

Rob: Alright. I know you have written a book about all of these, ‘How To Fly For Free: Practical Tip The Airlines Don’t Want You To Know.’ I think you have basically taken all your best secrets and put it into that book.

Scott: About that… The reason why I wrote that is because whenever I come back from the trips— from Vietnam or Bali, my friends will always ask me, “Scott, how can you travel so often? Are you secretly a millionaire?” I tell them, “I wouldn’t be able to do this if I was paying for all these flights and hotels. I don’t have nearly enough money for that. The only reason why I am able to do this was because I figured out these sorts of tips and tricks for using and generating all these miles.” Then rather than explaining to each person how the system works and what my tactics are, I decided just to compile them in this short eBook. I wanted to make it really practical for folks and it’s much more of a tutorial. It’s, here’s how you get the miles, here’s how you use them, here’s how you get the best value. And that’s why I wrote, How To Fly For Free. And then I put out a new book called, How To Fly in Cheap Flights. The purpose was to look in those instances when you are not playing frequent flyer miles, when you are paying out of pocket for a flight. What are all the steps that you should take to try to make sure you get the cheapest flight possible. All the steps that I go through. For instance, when I flew from New York to Milan in Italy for $65 each way, I tell exactly how I found that flight. When I flew from the US to Belgium for $115 each way, it explains, here’s exactly how I searched. Here’s exactly the types of searches that I ran in order to be able to find those flights. It’s a bit more practical because more folks are paying when you get a flight. But I figured these are some tips that some folks should know about in order for them to not pay in full price to the airlines.

Rob: I will link both of those books on the show notes. I noticed that you also have a site flyforfreeguide.com.

Scott: That’s right. I’ve got some sample chapters in there and the table of contents for each book just to show you what you are getting into, links to the books and link to me if you have any questions.

Rob: My concern to your website is that listeners will go to your site, look at it, and then email me and say, “Rob, why does your site looks so crappy and Scott’s site looks so beautiful?” Who designed that for you?

Scott: A hundred percent credit to my brother. He is an incredible web designer. He doesn’t even do this as a job, just in his free time. He enjoys and wanted to do this.

Rob: Do you have a day job?

Scott: I work as a journalist. I worked in Washington DC for four years working as a political journalist and then for the past year, I’ve actually been living down in Southern Mexico, also working as a journalist on their freelancing. But then also doing other stuff like volunteering, teaching English, learning Spanish. I’m going to be moving up back to the US and probably get back to the journalism but not 100 percent sure. I’m still weighing some options.

Rob: That’s great. I appreciate your time. Before I let you go, just one question. You mentioned 136,000 miles each for you and your girlfriend for the flight. But I think you said at the top of the show that you stayed in hotels virtually free as well. How did that happen?

Scott: A lot of the same sort of tactics. Almost every hotel chain— Marriott, Hilton, Inter-Continental and all the way down the line offer credit cards with incredible sign up bonuses that we would take full advantage of. They do a lot of promotions. For instance, a lot of times Marriott will offer this promotion where for every two times that you stay at Marriott they will give you a certificate for a free stay at any Marriott that they have. So we would have two paying stays at a really cheap Marriott along our way and then use the certificate that we got to stay in some really nice and expensive. Finding out those little types of hacks to be able to get good value from it… I think we’re on our road about 60 days or so and we had about a week and a half in my house in Weehawken and a week and a half at her relatives house in Ukraine. We had about 43 nights in hotels that we got from this. And these were not just roach motels. I was really blown away by how incredible they were. Ones that Barack Obama stayed at. Ones that the Queen of England stayed at. Ones that former President Bush stayed at. These incredible places that I never thought I would be at in my life, I was able to get access to from these hotel points. When we went back at the end of trip and we calculated that, if we had paid out of pocket for all the flights and all the hotels, how much would these have cost? Out of pocket, we paid cash about $440 or so. And that’s taxes and fees for all our flights, which are unavoidable. Then a couple of hotels in places that didn’t have chain hotels. The actual value that we’ve got if we paid out of pocket for all our flights and all our hotels, it’s over $14,000. So it was just remarkable to me that we got so much value out of these points that we got it basically for free.

Rob: That’s amazing. Do you have plans? Or have you already posted pictures from this trip anywhere online?

Scott: Yes. I like to post pictures mostly on Instagram. My account is scottkeyes and you can find that on the website at flyforfreeguide.com

Rob: Okay. I will also post a link to that as well.

Scott: Great. I appreciate it.

Rob: Scott, I really appreciate your time today. You’ve given us a ton of great tips and it makes me want to log back into Ward Wallet which I haven’t opened in months to see how many miles I’ve got. I really appreciate your time today. Thank you.

Scott: Thank you so much for having me. Great chatting with you.

Author Bio

Total Articles: 1083
Rob founded the Dough Roller in 2007. A litigation attorney in the securities industry, he lives in Northern Virginia with his wife, their two teenagers, and the family mascot, a shih tzu named Sophie.

Article comments

1 comment
daryn says:

that’s awardwallet.com, not wardwallet.com.