Travel Hacks From A Digital Nomad (My BEST Tricks Revealed) | The Growth Booth #95

Welcome to episode number 95 of The Growth Booth where today I'm going to be talking about one of the topics that I am most passionate about, something I've done a lot over the years, and I'm going to be sharing with you my very best travel tips, my very best travel hacks, the ways that you can live comfortably as a digital nomad, and just make your life that much more simpler, easier and more enjoyable when you are traveling, be it alone, for business, with your family on a vacation, or anything else for that matter. What I'm going to do is walk you through a scenario of what I go through when I'm booking a flight, when I'm preparing to travel, when I'm actually traveling, when I get to a destination, and everything in between. I'm going to drop a whole bunch of different tools, websites, apps, and tricks that I've picked up over the years and doing hundreds of flights all over the place.

Okay, so, for me, it all starts with searching for flights. So I get down, I figure out that I'm going to have to travel somewhere, and I start searching for a flight. The way that I do it normally is using kayak.com. There are different websites out there, but kayak.com is a good one. Skyscanner is another one. What these websites will do was to analyze all of the different flights that will get you from one place to another. Let me give you an example. Let's say I'm traveling from Buenos Aires, where I live most of the time, to London. There are lots of different ways that I could go, there are lots of different airlines, there are direct flights, there are connecting flights and everything else. Kayak, Skyscanner, and other similar websites like these will have a look at all of the different options, and then serve me up information about which are the options that are at my disposal. I can then choose which one I want to take. Now, that's a pretty good way.

I feel like using kayak.com will get you 80% of the benefit if you just want to book flights on your own. What I tend to do after I've identified a flight through the likes of kayak.com is then actually go and book not on Kayak, but from the actual airline. If Kayak is showing me that there are flights to London with American Airlines, then I'll actually go over to americanairlines.com and make my booking through that website. When I do that, I'll also make sure that I'm booking it through my frequent flyer account, so logging into American Airlines, and booking it that way. 

Now, in addition to using the likes of kayak.com, I've found more and more these days, I'm going back, as it were to the future, and using travel agents. I've got a couple of different travel agents that I use for different purposes, but I find that the more complex the travel is, the more value I get from using a travel agent. A lot of the domestic travel I do in Argentina, I actually do with a travel agent. Where there are lots of moving parts, like I'm traveling with my family, we're going to multiple different hotels, maybe there's multiple different connecting flights, then sometimes I'd like to use a travel agent as well. They just make it in my experience that much more streamlined and allow me to not have to worry about many of the bits and pieces that I would otherwise have to worry about, like how do I get from one place to another, how does it all work, am I missing anything… they just take care of all the heavy lifting for me. Oftentimes, the travel agent will actually get me better priced options as well that I can't see for whatever reason.

Now, when I'm booking my flights, if I'm doing it myself and not with a travel agent, I like to use flexible dates if I can. If I'm using kayak.com, then I can put that I've got flexible dates, maybe plus or minus three days or something like this. It will bring me back a matrix showing different options in terms of price. I can oftentimes save a lot of money by doing that. It takes me two seconds to do that. Because a lot of the time, I am quite flexible with my travel dates. It's just a great, simple way to get better flights. It's not always about saving money. Sometimes it's about getting a direct flight or a connecting flight that's got two- or three-hour connections in the middle versus eight or 10 hours. It's not just about saving money. It's just about finding better options and the more flexible you're out with your data, the more flexible your options tend to be. 

One thing I will say is over the years I've really started to be willing to pay more for flights that leave at certain times, or from certain airports and really pay a premium for flights that leave at times that I want them to leave at. So if I'm traveling with my family and I'm going on a long-haul flight, I inevitably want the flight to leave at 9pm or 10pm so that my kids can get a night's sleep on the plane. However, when I'm traveling on my own, sometimes I actually like to travel through the day.

Recently, I was in Miami, I went to the Formula One race up in Miami. I wanted to travel back during the day so that it didn't have a whole last day essentially and I didn't have an extra night, away from my family. So in that case, I actually took the option of going with a day flight to return from Miami. That was really effective for me. In fact, I get some of my most productive work done of all time. In fact, when I'm flying, so I definitely look at flight times, I think these do matter, and I take them into consideration when I'm buying my flights.

The other thing I'll say is whoever you're flying with, make sure you download the app that they've got. So there's an American Airlines app, there are apps for all the major airlines these days. They can make it so much easier when you're doing your check-ins to get updates about anything that may be happening with your flights. Just make sure you don't miss anything – it makes it that much easier to manage the flights when you are actually traveling.

Now the second tip that I've got for you is related to insurance. Back in the day, 15+ years ago or maybe 10+ years ago, I used to use a company called World Nomads, but I found that they got very expensive for what they were actually offering. And recently, maybe five or six years ago, I found another company called IMG. IMG provides, in my experience, really pretty good cover, especially for medical. I've actually had to make a couple of claims with them. I've traveled a lot and I have only made a couple of claims. Once on a recent trip a few months ago, my daughter got sick and was taken to a hospital in Switzerland. We took her into the hospital there, the Children's Hospital, we paid about $500-$600 for her to be seen by a doctor. Then when we got back to Buenos Aires, I logged in and I sent them an email, I sent them the receipt, and within a couple of days, they had returned that money back to my account. 

I've also used them myself when I've traveled to the United States. I had a throat infection of some kind and I had to go to the doctor and get antibiotics and so on and so forth, and the same thing applied. Really, really easy, simple to use. The things that I like most about the IMG Insurance, however, is not that I can get my money. I can make a claim because that's why these companies exist. If they made it too difficult to for you to make a claim, they'd probably go out of business. But what I really like about them, about IMG in particular, is I think it's really good bang for your buck. So if I'm traveling on my own, it's like $3, $4, $5 a day maybe to get health insurance from IMG. If I'm traveling with my family, then it might be like $3 or $4 per person per day, but that's for quite comprehensive insurance.

Now, you can also add on insurance to cover different items as well. If you want to have theft insurance or damage insurance or lost luggage insurance, you can add all of that on. I found it to be very, very cost effective. The way that it works is you choose a location that you're traveling to, and then based on that they've got different plans available with varying degrees of coverage, but it's definitely the insurance company that I go to every single time now. Something else that you might want to keep in mind though is oftentimes credit cards offer some kind of travel insurance as well. You can always inquire about that with your bank.

So at this point, we've used the likes of kayak.com to find a flight, we've identified a flight, we've purchased a flight, we've got our insurance, and it's time to start packing. What I've found to be the very best way to pack clothes is actually not to fold them up, but to roll them up. When I roll up clothes, it actually means that I reduce the wrinkles and it actually saves quite a lot of space as well. In addition to rolling up clothes, I like to use packing cells. What are packing cells? Packing cells are little bags, quite small bags about the size of a laptop or even smaller, lots more than that sometimes, and I use them to divide up where my clothes are. I'll put my t-shirts in one place. Maybe I'll put some jeans or something in another place. It means that it just makes it incredibly organized and easy for me to find things. I never really feel like I'm living out of a suitcase when I go traveling because I've got these packing cells. It just makes it incredibly simple to stay organized and I'm not rummaging around a big bag with 1000 different things in there. I'm just going to a specific packing cell. When you get to traveling with a family or with other people, then what we do is we've actually got color-coded packing cells, and this is kind of just the way that it's panned out. We've accumulated different packing cells over the years. My daughter can have one color, my son can have one, my wife can have one, and I can have the other, and that makes that even easier as well.

One question I often get from people is, and I don't know why, but I've had this question a few times is what's better, a hard suitcase or a soft suitcase, and I'm a little bit torn here. If I'm traveling on my own, I find the hard-shell suitcases to be pretty good. I feel like they obviously do a really good job of protecting the stuff inside. However, the soft-shell suitcases I think are more flexible. The soft-shell suitcases you can kind of open up like a bucket and just pile everything in, whereas the hard-shell is almost like a clam. You've got two pieces that need to fold together, so it can make packing a little bit more tricky. So overall, I'm someone that would prefer a soft shell, I think. I like to take a small suitcase as a carry-on, also a small backpack as a carry-on as well.

Something I always take if I'm planning on purchasing a few things when I'm away or coming back with more products than I went with, more items and I went with, is an expandable bag. I've got a really good, very durable, expandable bag that expands out to be around about the size of a suitcase, actually, but it folds down to be really, really small. I can just throw that in my suitcase, we take it away, and then if we end up buying things on our vacation or whatnot and we need more space, we've got that to come back to. So that's a little bit about packing.

The next thing you're probably going to do is head to the airport and get ready to jump on the flight. When I'm on the flight, there are certain things that I like to do that make the trip more comfortable for me. First of all, if I'm traveling on my own, I'll always be traveling business class and that makes a huge difference. If I am traveling for actually for business for work, then I find that I get there refreshed, and I can really hit the ground running. That alone is worth the price of upgrading to the business class. But beyond that, I just feel like it's so much better for me. In general, I just always feel better when I arrive. It was one of the things that I often thought about early on in my business career. When my business really started going well, I sort of hummed hard a little bit over, "Should I spend 4X, 5X, sometimes more the price of an economy ticket to go with business?" and it's just become a standard practice for me. It is a lot more expensive, but I don't think about "What else could I do?" If I traveled economy, I'm really thinking about it from an abundance mindset. I want to be able to travel the best way I can and not have to sacrifice or give up anything at the other end as a result of that. But obviously, depending on the situation that you're at, you might need to adjust that to fit your needs. But in my personal situation, I like to travel business.

What I'll do is I'll take noise-cancelling headphones. I used to take the over-the-ear headphones, I've had different ones: I've got the Apple ones actually up on the shelf here behind me which I use quite regularly, I've got Bose over-the-ear headphones as well, but the ones that I use when I'm flying, actually, the little AirPods, the little tiny inner-ear ones that Apple have come out with. I find that for me personally, the noise-canceling on those things is amazing. It can just slip into my pocket. It doesn't take up such a huge amount of space like the over-ear noise cancelling headphones used to. If I'm traveling on my own in business class, I won't take a neck pillow, but if I'm traveling with my family or something and we're not in business class, then I will absolutely take a neck pillow. My wife likes to use eye masks to give some darkness. I personally don't use that. I do however like to take an iPad with me and make sure I've downloaded entertainment so I'm not relying on the in-flight entertainment system which can be a little bit hit-and-miss whether or not I can actually find something that's any good. At least I know I've got my own iPad, I've got my own headphones, then I'm going to have good audio and I'm going to be able to enjoy that. So these are the small things, and these are things that, like I say, have come with doing dozens, probably hundreds of long-haul flights at this point.

The other thing that I do, so I mentioned that I have a carry-on suitcase, I also have a small carry-on backpack. I like to have that backpack down at my feet so I can easily get into things without having to stand up and get into the overhead lockers. I have a small flight bag, as I call it, I leave it at my feet, and it's got all my essential requirements in there. Maybe it's where I put my phone in there, I might have a snack or something in there. I might have an iPad, and then maybe from traveling with my computer, I might have a computer in there. I find that convenient to have at my feet throughout the flight so I don't have to be rummaging in the overhead lockers.

The other thing that I like to do to give me a little bit more comfort on flights is to pre-book my meal in advance. Now, this is something that you can often do from logging on to the airline where you actually purchase. Sometimes they'll let you pre book the meals in advance. I've been traveling in business class before and not been able to get the meal that I wanted because it had run out. This is not something that you want to have happen. I mean, especially if you're paying more money to get what should be a premium service, you don't want that to happen. But in economy class as well, oftentimes, I think almost all the time, they've got a certain amount of each type of food on the menu available. So if you're sitting right at the back of the plane, by the time they get to you, maybe they've only got pasta left, or maybe they've only got chicken left or something, whereas everyone has snapped up the most popular food first. If you pre-book your meal in advance, then you can avoid missing out on what you really want.

The other thing that I will always try to do during a flight is to stay hydrated, so drink lots of water. Normally, I don't drink alcohol on flights either. I just find that I don't get much reward out of doing that. In fact, I normally feel a little bit more parched, a little bit more tired and drowsy, when I get off the plane because inevitably I haven't been able to sleep quite as well. Alcohol will dehydrate you at the best of times, at the worst of times, but it will also dehydrate you when you are flying at 30,000 feet even more. I think that's why it's important to stay hydrated. If you are going to have a drink, don't go too crazy there, at least that's the way that I like to look at it. 

I like to use the lounges before I travel, and you'll get access to lounges normally if you're traveling with business, otherwise, if you're not traveling with business, but you're part of a frequent flyer category or something, then you might get access. Another way you can get access is sometimes through credit cards. If you've got an AmEx, you'll often be able to get to the American Express lounge. There are lots of other sort of ways that you can get into different lounges. I think that's worth exploring.

For me in the lounges, if it's a good lounge, that's where I like to actually have my meal. If I'm leaving on a late-night flight, like if I'm leaving Buenos Aires at 10pm, I'd much rather have a meal in the lounge with good food from the lounge. Before I board the flight, this will allow me to just eat before traveling, and I think I tend to get a bit of sleep, but that will kind of depend a little bit on what time the flight is actually leaving. That's something I do on the flights that are leaving much later at night.

There's another app that you can use, and it's called Flighty. Flighty will give you more information about your flight, or it's available on the PA systems. You can find out whether or not you're going to have a delay on your flight before you actually might find out any other way. I don't know exactly how it works, but it works and works pretty well for the most part.

In terms of which seats to sit in, I think this is personal preference. I mean, if you buy the aisle and you're someone that gets up and down a lot, then maybe this is going to be a bit easier for you. But if you're someone that doesn't really get up and down that often in your flight, then you might prefer to be by the window. One thing I will recommend is a website called Seat Guru. At seatguru.com, you can put in your flight number, the day that you're flying, the airline that you're flying with, and you can have a look at and see exactly what kind of seat you're going to get, where it's going to be, where it's positioned on the plane, the pros and cons, things that other travelers have said about it, any issues that it might have, and so on and so forth. This is something that I absolutely use when I'm booking flights for myself because I think there oftentimes is quite a bit of difference between one seat and another, so Seat Guru is a good one there.

Couple of things I found traveling with kids, now there are inflatable pillows that you can sort of get. They're not really pillows, they're more like platforms, and they will sort of fill up the space where an adult's legs would go in the economy section of the plane. The good thing for little clips, though, is that this basically transforms the economy seat. If you get a couple of these things, that can transform it into somewhat of a bed. It's been quite effective with our kids, particularly when they were younger, to allow them to almost sort of lie down a little bit more. In New Zealand, I've actually got something really cool. I haven't seen this on any other airline, I think it's trademarked or copyrighted in New Zealand or something, but it's called Skycouch, and it's where an economy row of seats, so three seats, will transform into a bed, and you can lie down on that. You could book out those three seats for yourself and lie down on it. What my wife and I will typically do is we will book out two rows of three seats. I'll be lying down on one of the seats with my son or my daughter, and she'll be lying down on the other one with the other kid. That's a really comfortable way of traveling and really good bang for your buck. But again, that's only something I've seen on in New Zealand.

Now, once you arrive at your destination, you're going to be starting to think about accommodation. In fact, you will probably hopefully take care of this before you actually depart. We've gone back and forth a lot over the years between Airbnb and also using the likes of booking.com. Hotels.com was one we used for a long time, they had a really good loyalty program, but that loyalty program is terrible nowadays. I wouldn't necessarily use recommend you use that, but booking.com is still good to get a good cross section of availability and identify different hotels. When I'm booking accommodation, normally, I like to first and foremost book based on the location, and then on the grade of the hotel. So if I'm looking for a five-star hotel in a certain location, then I can use the likes of booking.com, even hotels.com, and narrow my search down to just be looking at those kinds of properties. 

Airbnb, we've had some great experiences, and we've had some mixed experiences with this. I think as my kids are getting older, we're preferring hotels a lot these days. When they were younger, Airbnb was good, because it gave us a bit more flexible facilities sometimes for doing cooking and bits and pieces with the kids. But oftentimes, you can get that through hotels anyway. I think there's more clarity around what you're actually going to get, whereas Airbnb can be a little bit hit and miss sometimes. So overall, I think I definitely prefer hotels and going with booking.com to filter through them, and then if possible, I like to use the different loyalty programs as well.

All the major hotel chains are aligned with one of the different loyalty programs for the most part, and you can find out about those if you just go to the hotel websites. Similarly when I'm booking hotels, I'll use booking.com the same way I use kayak.com for finding flights. So I use booking.com for finding hotels, but then before I reserve the hotel, or sometimes go over to the actual hotel website. Sometimes I booked through the air, I feel like I can get a better service by doing that. By the way, all of this research and administration is something that you can have someone else doing for you. I'm just sort of walking you through the process so you can see how I do it, but it's not always the case of me doing it. Sometimes I'll have a virtual assistant doing it, sometimes I'll ask a travel agent to take care of it for me, but the general process is like what I'm sharing with you here.

Now a couple of other things when you're thinking about hotels, most of them have some flexibility around check-in and also check-out. Normally if I'm arriving early, I'll ask for an early check-in, and if I'm leaving late, I'll ask for a late check-out. Most of the time, I'd say 90% of the time, there's a bit of flexibility there and it just makes my life a little bit easier. Now, there are not many places like Las Vegas. Las Vegas is a pretty interesting and unique place, and one of my good friends once shared a tip with me which I've used on multiple occasions now in Las Vegas to get a much better room. So I thought I'd share that one with you here. The trick to getting a bit of room in Las Vegas is to offer the person that's helping you do your check-in a tip when they are in fact doing your check-in. The way this typically works is you might have a $50 note or $100 note, and when you're doing the check-in, you'll just put that on the on the counter and say, "Look, are there any special room upgrades or other upgrades that you can give me?" I've used this multiple times in Las Vegas, and it has been transformational. I've been able to get into rooms much, much earlier than when I've already been told that there are no rooms available. I then use the "Is there anything you can do for me here?" sliding, $100 or a $50 bill across the counter. All of a sudden, all the problems are solved.

For another case, I was doing a longer stint in Las Vegas. In fact, I think it was there for even a couple of months, I had multiple seminars, and this was probably eight or nine years ago, and I was there with my wife. When we were checking in, I did the same thing, and this time because I was there for such a period of time, I think I slid may have been a couple of $100 over the counter. Keep in mind that the cost of the hotel was probably several hundreds, maybe $400 a night kind of a thing, and so a couple of $100, in the scheme of things, wasn't a lot of money. But I used this tip, and what they ended up getting us was a by far superior room on a much, much higher floor with a great view. It also got us a I think it was like a $20 per day voucher to spend in the shop, which was brilliant, because that was the shop inside the hotel where we could get our food and beverages and all that good stuff. So that was a $20 per day voucher. Remember, I was there for weeks on end, so that alone paid for it. I was also able to get complimentary upgrade to the fast internet, which obviously in my line of work was quite beneficial for me. All of this just for a couple of hundred bucks.

If I bought these things individually, it probably would have cost me an extra $1000 or even maybe a couple of thousands because in Las Vegas, all of these things are expensive. Keep in mind that we were getting a $20 voucher every single day while we're on the resort. That's a tip that has never let me down in Las Vegas. There's not really any rocket science to it, but when you're doing your check-in, you just nicely ask if there's any upgrades or anything you can get, anything that the person helping you can do to help you have a more comfortable say, and giving them a tip essentially… goes a long way there. I've never had someone take the tip without giving me some kind of upgrade, which was by far worth what the tip was valued at. So I think it's pretty much a no-brainer there.

The next thing that you might be wondering about when you're in a place is how to get around. I think this depends where you're going, what you plan on doing when you're getting there. But for me, if I'm renting a car, then I will typically have a travel agent or a virtual assistant go through and check prices with and find the best car to meet my needs. Again, it's not always based on price. In fact, one of the criteria that I have is if I'm renting a car, I want to be able to pick it up right from the terminal. I'm done with traveling 20 or 30 minutes on a shuttle to get to my rental car. I just want to be able to land, go and get the car key and be off in a flash. I want to make sure that if I'm renting a car, I can get it from the actual airport terminal. That's the first thing. If I'm doing this myself, I’ll typically identify what are the top three or four big car rental companies that the airport has, and then I'll just quickly check each one, or otherwise I'll have my virtual assistant or travel agent actually do that for me, and then I can very quickly identify what the options are and go with one of those.

The car rental companies have loyalty programs as well, and quite often they're tied to the airlines. There's an opportunity there to get some extra sort of bonus frequent flyer points. And then if you're not renting a car, look at the likes of Uber. This will also depend on sort of where you are in the world. But in time when I'm in the United States, I use Uber a lot. If I'm on foot or using subway systems and so forth, then Citymapper is a fantastic app. You might think, "Why would I use Citymapper if I can just use Google Maps?" Citymapper is so good because it gives you all the different options that exist in a local area. Now Citymapper is not for every single city in the world, but it's probably got the top 100 cities or something that tourists go to. I found it to be incredibly good whether I'm on foot, whether I'm on a bike in Paris like I was recently, whether I'm using subway systems, taxis, Ubers, whatever it might be. So Citymapper is really good.

The next thing that is a consideration for me when I'm traveling is where am I going to be eating? I like to use apps and really lean into reviews. If I'm going to go to a restaurant, I want to make sure that it's got really good reviews. I like to use Google for this. I will also have a look at Yelp, sometimes it's good for identifying restaurants in certain areas, and then I'll do my booking quite often with an app called OpenTable. Again, these kind of apps vary where you are in the world, but these are the ones that I normally use: Yelp, Google, OpenTable, and I will book based on ratings. I think, over time, I've got a bit more pickier. I've got higher expectations of what I want from my food. But I think if I'm just traveling, and I'm out and about going somewhere new, if I can, it takes me 30 seconds to find something which has got really good reviews, and then I know I'm going to get a good meal and enjoy it that much more.

The final few things I've got for you here today that sort of fall into the miscellaneous bucket, if you like, are ones relating to money. You want to make sure you notify a bank before you travel because if you start using your credit card halfway around the world, then don't be surprised if your credit card gets locked down. That's not what you want, it can look like someone's stolen your credit card. You don't want that to happen to you when you're traveling, so just notify the bank before you go where you're going to be going.

Another tool that I use is a VPN. This allows me to login to different accounts that I've got that may raise a security alert, otherwise, if I log into them from a different location. I can set my location to wherever I want it to be, the United States, Argentina, New Zealand, wherever, and login just as I always would without tripping any trip-wise as it were and getting locked out from a security standpoint,

I like to travel with an ultra-small laptop. So I'm talking about MacBook Pro or MacBook Air that are 13 inches. It's around about the size of the iPad Pro, which is something else, which I find quite good to travel with. It's super lightweight, I mean, especially the MacBook Air, and it doesn't have to be an Apple product. There are similar products out there from Asus and Samsung and all the PC brands as well. The point is a lightweight, slim laptop is absolutely the way to go.

I also like to get international roaming, this is something I set up before I leave. This is probably different country to country but where I am in Argentina, I can just add a simple pack and that'll give me unlimited bandwidth and roaming capability. I don't have to worry about getting a local SIM. I used to sometimes get a local SIM, but the international roaming seems to have gotten so much better these days that those aren't needed anymore. The other thing I'll mention is if I am in place for an extended period of time, sometimes I look at getting another phone number. With the latest smartphones, I use an iPhone, with the latest iPhones and smartphones in general, you can have multiple phone numbers on the same phone now. So when I was in New Zealand over the summer, the New Zealand summer, I could have a New Zealand eSIM. It's not a physical server, it's just a New Zealand phone number on my phone. I still have my Argentine phone number, I could have multiple different phone numbers if I wanted all coming in to the same device. I found that to be quite effective as well when I'm going to be in a place for a period of time.

So look, this is a bit of a brain dump of travel hacks. I hope you found it useful. These are things that I've picked up from a couple of decades of doing a lot of travel, travel on my own, travel with my family, travel for business, travel for pleasure, everything in between, and traveling to I think over 50 countries and hundreds of cities around the world. I would love to know what I've missed. As always make sure you comment on social media, send me a private message, send me an email. I'd love to hear what your favorite travel hacks are and find out how I can sharpen my sword as it were with regards to travel. Thanks for listening.

As always, you can get the show notes over at thegrowthbooth.com, navigate to episode number 95. You'll get a transcript of this. You'll see links to all of the different services and tools that I've recommended. I hope that this makes your traveling that much more comfortable and that much more enjoyable. I'll see you on the next episode of The Growth Booth.