One of my greatest passions is travelling. It’s one of the reasons I got into Internet marketing in the first place — I could work from anywhere. It was through travelling where I met my future wife, and our long distance relationship back then encouraged even more travelling… which meant even more motivation to generate a sustainable online income!
Today I’m going to be sharing with you my very best travel hacks, and the ways that you can live comfortably as a digital nomad. There’s also a podcast on this topic, you can watch below:
I’m going to discuss a bunch of hacks, such as:
- Booking a flight
- Preparing to travel
- Actually travelling
- Accomodations, Transportation
- And everything in between!
You’ll also find out about a bunch of different tools, websites, apps, and tricks that I’ve picked up over the years and doing hundreds of flights all over the world. Here we go!
Searching For Flights
What these websites do is analyze all of the different flights that will get you from one place to another. Here’s an example: let’s say I’m traveling from Buenos Aires, where I live most of the time, to London, England. There are lots of different ways to get there, with lots of different airlines.
Kayak, Skyscanner, and other similar websites 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.
I feel that 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 is to actually go to the airline’s website and book there. If Kayak is showing me that there are flights to London with American Airlines, then I’ll go over to Americanairlines.com and make my booking through there.
When I do that, I’ll also make sure that I’m booking it through the frequent flyer account I have with them to gain points.
Using Travel Agents
Interestingly, I’ve found more and more these days that I’m going back to 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.
This is especially true where there are lots of moving parts. If I’m traveling with my family, we’re going to multiple different hotels, and maybe there’s multiple different connecting flights, then I’m more than likely to use a travel agent.
In my experience, they just make the process that much more streamlined and allow me to not have to worry about all the details and bits and pieces. It is their job to 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.
Be Open To Flexible Times
When I’m booking flights by myself, I like to use flexible dates if I can. If I’m using kayak.com, then I can add the option that I’ve got flexible dates, maybe plus or minus three days. It will bring me back a matrix showing different options in terms of price, and I can often save a lot of money by doing that.
It’s not always about saving money. Sometimes it’s about getting a direct flight or a connecting flight that has a 2 or 3 hour connection versus 8 or 10 hours. The more flexible you are with your dates, the more flexible your options tend to be.
Over the years I’ve become more willing to pay more for flights that leave at certain times, or from certain airports. 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, when I was in Miami, I went to the Formula One race there. I wanted to travel back during the day so I wouldn’t have to stay an extra day and night away from my family, so I opted for a day flight to return from Miami.
That was really effective for me. In fact, I get some of my most productive work done during a day flight, and I often take this into consideration when booking.
Whoever you’re flying with, make sure you download the app that they’ve got. 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.
Back ten or fifteen years ago, I used to use a company called World Nomads. However, I found that they got very expensive for what they were actually offering.
About five or six years ago, I found another company called IMG. IMG provides, in my experience, really good coverage, especially for medical. I’ve actually had to make a couple of claims with them. Once on a recent trip a few months ago, my daughter got sick and was taken to a hospital in Switzerland. We paid about $500-$600 for her to be seen by a doctor in a children’s hospital.
When we got back to Buenos Aires, I logged in and I sent in a claim by email, 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 it was really easy to go through their claims process.
The thing I really like about IMG is that I think it’s really good bang for your buck. If I’m traveling on my own, it’s $3 – $5 a day to get health insurance from them. If I’m traveling with my family, it’s about $3 or $4 per person per day, and that’s for well-rounded, comprehensive insurance.
Now, you can also add on insurance to cover different items as well. If you want to have theft, damage or lost luggage insurance, you can add all of that on. The way that it works is you choose a location that you’re traveling to, and based on that they’ve got different plans available with varying degrees of coverage.
Something else to keep in mind is that some credit cards will offer some kind of travel insurance as well. You can always inquire about that with your bank.
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 means that I reduce the wrinkles and it saves quite a lot of space as well. It’s just a more organized way to pack.
In addition to rolling up clothes, I like to use packing cells. So what are these? Packing cells are little bags about the size of a laptop or even smaller, 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 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. I’m not rummaging around with 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, we’ve actually got color-coded packing cells. My daughter has one color, my son has another, my wife a third color, and I can have the final.
Hard or Soft Suitcase?
One question I often get from people is, “What’s better, a hard suitcase or a soft suitcase?” 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 are more flexible. They open up like a bucket and you 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 trickier.
So overall, I think I prefer a soft shell.
For carry-ons, I take a small suitcase and a small backpack. I also take an expandable bag if I’m planning on purchasing a few things when I’m away, or coming back with more products than I went with. I have a really good, very durable, expandable bag that expands out to be around about the size of a suitcase, but also folds down to be really, really small.
I can just throw that in my small suitcase, and if we need more space, we’ve got that to use.
Before and During 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. This makes a huge difference. If I am traveling 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 business class.
Going business class was one of the things that I often thought about early on in my career. When my business really started taking off (no pun intended), I hummed and hawed over it, asking myself, “Should I spend 4x, 5x the price of an economy ticket and go with business?”
Yes, it is a lot more expensive, but 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 saving money.
But obviously, depending on the situation that you’re at, you might need to adjust to fit your needs. But in my personal situation, I like to travel business class simply so I feel more refreshed at the end.
I always take noise-cancelling headphones. I used to use over-the-ear headphones, such as Apple Max and Bose, but now when I’m flying I actually use the little AirPods. I find that for me, personally, the noise-canceling on those things are amazing. It can just slip into my pocket. It doesn’t take up such a huge amount of space like the other 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 we’re not in business class, then I will absolutely take one.
My wife likes to use eye masks for some darkness when sleeping. I personally don’t use that.
I 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 often be hit-and-miss.
As I mentioned before, 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 bins. My little “flight back” has my phone, a snack, my iPad, sometimes my laptop if I need to work, and my AirPods.
Pre-Book Your Meal
The other thing that I like to do to give myself a little bit more comfort on flights is to pre-book my meal in advance. You can often do this by logging onto the airline where you actually purchase your ticket. Sometimes they’ll let you pre book the meals in advance as well.
I’ve been traveling in business class before and not been able to get the meal that I wanted because it had run out. Especially if you’re paying more money to get what should be premium service, you don’t want that to happen.
In economy class as well, they have 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, everyone else might have 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.
Premium Airport Lounges
I like to use the lounges before I travel, and you’ll normally get access to them if you’re traveling business. You could also get access if you’re part of a frequent flyer category. If you have an American Express credit card, you’ll have access to their special lounges as well.
I’d also rather have my meal in the lounge, when I can. Especially If I’m leaving on a late-night flight, I’d much rather have a meal there, as the food is often better. Then I have the option of trying to get some sleep on the flight rather than have to worry about eating later.
A great 3rd-party app I like to use is called Flighty. It gives you more information about your flight, and you can often find out whether or not you’re going to have a delay before you find out other way.
In terms of which seats to sit in, I think this is personal preference. If you’re someone that gets up and down a lot, the aisle seat is going to be easier for you.
If you’re someone who doesn’t get up and down often, you might prefer to be by the window.
One thing I will recommend is a website called Seat Guru. You can put in your flight number, the day that you’re flying and the airline that you’re flying with. You can then 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 I absolutely use when I’m booking flights for myself because I think there’s oftentimes quite a bit of difference between one seat and another.
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, if I drink alcohol I feel a little bit more parched and a little bit more tired and drowsy when I get off the plane because I haven’t been able to sleep quite as well.
Alcohol will dehydrate you at the best of times (that’s one reason why you have a hangover), but it will also dehydrate you even more when you are flying at 30,000 feet. That’s why it’s important to stay hydrated.
Travelling With Kids
A couple of things I found with traveling with kids: check out inflatable pillows. They’re not really pillows, they’re more like small platforms, and they will fill up the space where an adult’s legs would go in the economy section of the plane.
The good thing for little kids is that this basically transforms the economy seat into a kind of bed. It’s been quite effective with our kids, particularly when they were younger, and allows them to lie down a bit more.
On Air New Zealand, they actually created a really cool product called Skycouch, that they’ve licensed to a couple other airlines (Lufthansa has their “Sleeper Row” as well.)
It’s where an economy row of seats (so three seats), will transform into a bed, and you can lie down on that. You can actually book those three seats for yourself to use as a couch or bed.
What my wife and I will typically do is book two rows of three seats. I’ll be lying down on one of the seats with my son or daughter, and my wife will be lying down with our other child. That’s a really comfortable way of traveling and really good bang for your buck.
Now, once you arrive at your destination, you’ll likely be on your way to your accommodation. Of course, you will hopefully have taken care of this before you actually depart.
Hotels.com was one we used for a long time, but I found that their loyalty program has really deteriorated. Booking.com is still good to get a great cross section of availability and identify different hotels.
When I’m booking accommodation, 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, I check out Booking.com, (even Hotels.com still, sometimes), and narrow my search down to just be looking at those kinds of properties.
We’ve had great and mixed experiences with Airbnb. I think as my kids are getting older, we’re preferring hotels more these days. When they were younger, Airbnb was good because it gave us more flexible facilities for cooking and having living areas to play 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 at hotels, whereas Airbnb can be a little bit hit and miss.
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 their website engine for finding hotels, but then go to the actual hotel website to reserve.
Most hotels have flexibility around check-in and 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.
Transportation of course depends on what you plan on doing at your destination. 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.
It’s not always based on price. In fact, one of the criteria that I have when I’m renting a car is that 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 just 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.
If I’m doing this myself, I’ll typically identify what the top three or four big car rental companies in the destination airport, and I’ll quickly check each one (or have my virtual assistant or travel agent do that for me.) I can very quickly identify what the options are and go with one of those.
Most car rental companies have loyalty programs as well, and quite often they’re tied to the airlines. Thus, there’s often an opportunity to get bonus frequent flyer points.
If you’re not renting a car, look at the likes of Uber. This will also depend on where you are in the world. In the United States, I use Uber a lot.
If I’m on foot or using the subway systems, Citymapper is a fantastic app. You might think, “Why would I use Citymapper if I can just use Google Maps?” Citymapper is great 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 that tourists go to. I found it to be incredibly good whether I’m on foot, on a bike in Paris like I was recently, whether I’m using subway systems, taxis, Ubers, or whatever else it might be.
The next thing that is a consideration when I’m traveling is where to eat. 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 look at Yelp as well, sometimes it’s good for identifying restaurants in certain areas.
Quite often, I’ll do my booking 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 pickier about food. I now have higher expectations. If I’m going somewhere new, and it takes me 30 seconds to find something which has really good reviews, I know I’m going to get a good meal and enjoy it that much more.
#1 Las Vegas Tip
Las Vegas is a pretty interesting and unique place, and one of my good friends once shared a tip with me that I’ve used on multiple occasions to get a much better room.
The trick is to offer the person that’s helping you do your check-in a tip when they are in the process of doing your check-in.
The way this typically works is you might have a $50 note or a $100 note, and when you’re doing the check-in, you’ll just put that 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. Or if there is some problem, all of a sudden all these problems are solved.
For another case, I was doing a longer stint in Las Vegas, a couple of months, in fact. This was almost a decade ago, I had multiple seminars, and I was there with my wife. When we were checking in, I did the same thing, and because I was going to be there for a longer period of time, I slid a couple of $100 over the counter.
Keep in mind that the cost of the hotel was about $400 a night, so a couple of $100 bills, in the grand scheme of things, wasn’t a lot of money.
But I used this tip, and what they ended up giving us was worth thousands of dollars! First, we got a far superior room on a much higher floor, and with a great view.
It also got us a $20 per day voucher to spend in the shops, which was brilliant, because there was a shop inside the hotel where we could get our food and beverages and toiletries. Remember, I was there for weeks on end, so that alone paid for it.
I was also able to get complimentary upgrade to the fastest internet, which obviously in my line of work was quite beneficial for me.
There’s not really any rocket science to this. When you’re doing your check-in, you just nicely ask if there are any upgrades or anything else you can get, anything that the person helping you can do to help you have a more comfortable stay, and giving them a tip. It goes a long way there.
Final Travel Tips
Here are a couple final tips for travelling:
Notify Your Bank
You want to make sure you notify a bank before you travel, because if you start using your credit card halfway around the world, your credit card might get locked down, as it looks like someone’s stolen your credit card.
Use a VPN
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 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, and login just as I always would without tripping any security and getting locked out.
Bring a Small Laptop
I like to travel with an ultra-small laptop. I’m talking about the MacBook Pro or MacBook Air that are 13 inches wide. It’s around the same size as the iPad Pro, which is something else I find quite good to travel with. It doesn’t have to be an Apple product, of course, just look for something slim and lightweight.
Avoid Roaming Charges
I also make sure to set up international roaming 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 card.
If I am in a place for an extended period of time, I sometimes look at getting another phone number. With the latest smartphones, you can have multiple phone numbers on the same phone now.
So when I am in New Zealand, I have a New Zealand number. I still have my Argentine phone number, and I can have multiple different phone numbers if I wanted, all coming in to the same device.
I hope you found these travel hacks useful. These are things that I’ve picked up from a couple of decades of doing a lot of travel, both on my own and with my family. I’ve travelled to over 50 countries and hundreds of cities around the world.
I would love to know what I’ve missed, let me know in the comments below! I’d love to hear what your favorite travel hacks are, and find out how I can sharpen my sword with regards to travel!