Being a combination of remote worker and having a partner who loves travel has forced me to continuously evaluate my travel gear and setup to get the most out of the trip. This is a collection of tools and tips I’ve tested, updated, discarded, updated and then tested again throughout travelling both domestically and globally for personal vacations and work trips. The goal has been simple: do travel with as little as possible while still maintaining a stress-free and comfortable experience.
Note: None of the links I’ve used below is for affiliates or referrals or anything like that, just good ol’ fashion links to the thing you care about.
At heart, I do favour using the right tool for the job and sometimes paying a bit extra for the better quality that will last you a long while over many cheap replacements. I’ve been caught out by buying cheap in the past and can assure you, when it comes to travel you can often be looking at more than the cost of a cheap replacement when they break down on you.
Hardshell Samsonite Roller bags: My wife purchased a set of 3 of these a couple of years ago and they have served us well. Built extremely light, they are also very tough so that your belongings can’t be damaged if the baggage handlers are having a rough day. We take these on our trips where we both travel or we’re going international.
Incase Travel Duffle: This is my go-to for trips under a week and all international flights as carry on.
Peak Design Tech Pouch: A relatively new addition to the tool belt however it’s already proven how efficient it is for storing the cables, adapters, external hard drives and power banks while still not being too bulky.
Fisher space pen: Carrying a pen is a must for travelling internationally. I purchased two Fisher Space pens a couple of years ago and they have never let me down. The AG7 is my daily driver and I use the 400B when travelling.
Bellroy Travel Wallet: This is the only part of my international kit that I’m still unsure of. I usually carry a very small wallet (the equivalent of The Low from Bellroy) so this wallet feels a touch too big to be carrying it everywhere but it’s great otherwise. The extra-deep note compartment for bigger notes, SIM card holder and ejector tool space have all been very handy. The pen is very convenient for filling out immigration forms. Before this wallet, I was using a Muji Passport holder which worked well but wasn’t something I took out of the hotel once I arrived.
Good quality sunglasses. I’ve worn a pair of polarised Ray Ban Justin’s for about 3 years now and take them everywhere with me. Whether it’s an early morning flight or walking about the city, these are a godsend to save your eyes.
Privacy and security
I’m what you’d call “privacy and security conscious”. As such, I have a pretty high bar for what I deem secure or where my privacy is concerned.
For those looking to increase their privacy and security stance, here are a few things I do when travelling.
Use a dedicated travel device. I started writing about this process but Filippo Valsorda has already beat me to it with a great in-depth article which I highly recommend checking out.
VPNs, 100% of the time. I have both a commercial VPN provider as well as a handful of cloud instances that are running Wireguard, OpenVPN using stunnel and dsvpn. I keep the commercial one handy for quickly testing in multiple regions where I don’t have the infrastructure and something for my wife to easily use on her devices.
1Password Travel mode. For credentials and sensitive data storage, I use 1Password. It ships with something called Travel Mode whereby it removes anything that you don’t want to be there without compromising your ability to access the data if needed. This is great for crossing through airports or being in an environment where you don’t know who might end up with access to the device or data.
As a rule of thumb, I don’t take anything of a sensitive nature with me when travelling. This includes things like laptops which if they do come with me for work, end up pretty much wiped and set up upon arrival to ensure if a device copy is made, nothing important is taken.
Applications I use
Flighty: This application was only released this year however it has been a game-changer when it comes to notifications, updates and flight information. I rarely bother to check airline or airport websites now for things like delays or gate changes as this app beats them every time. The UI is also amazingly well designed and Just Looks Really Good when you’re using it.
TripIt: Trying to keep track of flight itineraries, taxis, hotel accommodation and any events information used to be a pain as I would keep them all in my inbox (or separate applications) and then just rely on my memory or notes to keep track of what time everything would be needed. This didn’t scale well and made things more stressful than what they needed to be. Now I send all of the information regardless of activity type to TripIt and it plans it all out for me. Whether it’s a 3-day stint to HQ or a 2-week multi-leg flight and accommodation with private transfers for vacation, it’s all organised and never forgotten.
TimeShifter: Australia is pretty amazing for the most part; you’ll struggle to find a better option for a country to live in. That is, as long as you never deal with timezones which is pretty hard because almost everywhere you travel outside the country is often a timezone shift by at least a few hours. Jet lag is never fun and I’ve had my fair share of tired sightseeing trips to know it’s a real thing and can get in the way of enjoying parts of your trip. While on holiday Thailand a few years ago, I was looking into the usual “how to beat jet lag” google links and stumbled on an approach that instead of relying on hope and supplements, used science-backed techniques to adjust your circadian rhythm. This has been great on my overseas trips since and beats waking up at 2 am and not getting back to sleep or needing to go to bed at 5 pm because of the timezone differences. The application makes this process simple and prompts you as to what actions you should be taking in the lead-up and arrival to your destination to get the most out of both timezones.
Airline entertainment apps: Most airlines have an application you need to download to access their in-flight entertainment. I only have a couple of these as we stick to the same airlines when travelling. Best to download these at the airport if you haven’t already got it as by the time they take off, it’s too late.
Foursquare : It’s always tough to find restaurants and activities when you’re not a local and don’t have a guide. I’ve been using Foursquare on all my trips and have found it to have the most accurate and honest reviews. I’ve used other apps in the past that were either quite biased or didn’t have the same level of information available about locations or activities. A bonus here is that things like price, WiFi speed and transport options to get to the destination are commonly included.
Apple Wallet: I download all my boarding passes to Apple Wallet to ensure I can’t lose them. This also means one less piece of paper to carry around. If you don’t have iOS, you can also take a screenshot of your boarding pass to present and this would achieve the same thing.
TripMode: Bandwidth is expensive when roaming. Don’t let your apps run up a bill on you. This application operates as a gatekeeper for your other applications and puts you in control of managing who can download while you’re out.
Little Snitch: Little Snitch is a great tool that I use every day (regardless of travel) to know what process on my machine is connecting to the outside world. When I travel, I up the mode to be super locked down. This prevents my data from going out on things like hotel wifi but also saving bandwidth. This is similar to TripMode, just more in depth with finer grained controls.
iPad mini. Before any travel (be it 2 hours or 12 hours) I load my iPad up with things to do on the flight. I do the majority of my reading on my iPad these days (aka an expensive Kindle) but I also download TV shows/movies in case the flight doesn’t have inbuilt entertainment.
Headphones. I pack two pairs of headphones. My Bose QC35s and the Apple wired earbuds.
All the adapters/chargers. I carry all the adapters/chargers/cords for my devices in my Peak Design Tech Pouch. The only specific one worth calling out here is having a shorter cable on the flight for your phone/tablet to avoid having an extra cable dangling and potentially tripping over.
Lip balm. No one likes cracked or sore lips on a flight.
Moisturiser. Your skin ends up dehydrated during and after flights. Help it out with some moisturiser.
Empty water bottle. Same as above, but for your insides. I take my Yeti and fill it up in the airport after getting through security. My Yeti also doubles as a muscle roller in my hotel room if my back ends up sore or tight. There are some whizz-bang alternative water bottles that collapse too if you’re looking for a space-savvy option.
Sanitiser wipes. While planes are visibly clean, they aren’t sanitised between every flight. If the person who sat in your seat on the incoming flight was sick, you could be one touch away from getting sick. Wiping down the area where you’re sitting avoids this and catches any of those sticky food spots before you find them mid-flight.
Wet Ones. Flights can be hot and stuffy. Do everyone a favour and freshen yourself up before landing or just after landing in the airport bathrooms.
Tissues. You can never find one when you need it.
Toothbrush and toothpaste or mouthwash. If you manage to sleep on that overnight flight, you’re going to wake up with goat breath. Don’t put flight attendants or the good people at immigration through needing to smell your breath.
Change of clothes. If you’re flying domestically, this could be all your clothing but it’s also handy to pack a change of clothes for international travel (especially if you’re wearing your comfy clothes on the flight or manage to spill something on yourself). At a minimum, fresh shirt, pants and underwear.
Power bank. I bought a power bank for my working from cafè days to charge my 13” MacBook Pro which used to come everywhere however I found it was a bit overkill for my domestic needs where I may only need to charge my iPad or iPhone (who needs to fully charge their iPad 5 times on a 3 hour flight?!?!?). I ended up buying a smaller one as well and swap them according to the type of travel I do.
Pain killers. I pack a handful of Panadol to account for getting headaches or dealing with backaches and pains.
Powerpoint adapters. I tried a universal all-in-one style of adapter only to find that some power points didn’t account for these very well and the configuration knobs would block the second outlet. I now opt for a dedicated one based on the destination but still on the lookout for a single solution here.
For domestic flights where I’m travelling alone, I only do carry on. I’ve only had two occasions where my checked baggage was “lost” (in both cases, less than 8 hours) however it taught me a very valuable lesson that you can’t lose a bag that doesn’t leave your side. A side benefit of this is that I’m less likely to overpack because I’ll be restricted on the size and weight.
If the trip is longer than 4 or 5 days, I don’t pack for the full trip. Instead, I opt to use the hotels’ laundry service. This is a great, cheap alternative to overpacking. You get the laundry bag out of your room, put the dirty clothes in it and then let the front desk know you have something to go. My last bill for 3 days worth of clothing and a jacket was under $5.
When I’m flying with my wife, we do a setup close to my international approach as we can quite often share checked-in luggage and the carry on is just a nice to have.
Before travelling internationally, I go on a bit of fact-finding mission first. This ensures that I know what sort of hurdles (if any!) I’m going to run into while abroad. This preparation includes things like:
- Being aware of any restrictions that are present in the country. Internet censorship, religious or cultural differences, etc.
- Whether I need to brush up on my language skills. Many countries respond better to you when you use a basic language vocabulary in their native tongue. I don’t learn all the language, just enough to get by without butchering their language.
- Expected prices and costs. This cost of living calculator from numbeo.com is great for knowing how much you should be paying and when to know if you’re getting ripped off.
- What payment type the country prefers. I always take cash and a credit card however I do prefer to know which form of currency will be the most widely used so that I can load up more on that instead of needing to top it up while I am there.
My international packing is quite similar to my domestic except I also check in a bag for my clothing. My carry on does become a little more extensive though as it also needs to account for if my checked baggage ends up lost and I only have those things available to me.
I pack miniatures of my personal hygiene products in my carry on and full-sized items in my checked bag. For example, a 50g deodorant goes in my carry on and my usual 180g goes in my checked bag. This approach allows me to stay refreshed on long haul flights and not feel like I’ve rolled out of a gutter after a weekend bender.
Up until recently, lounge access wasn’t something I was too fussed with. That was until my wife’s employer paid for a business class flight and access came with the ticket. Boy oh boy, does it make a difference. Nicer chairs, easy access powerpoints and of course, a pretty stocked bar and food buffet. Lounge access is one of those things that make your trips a little less stressful as they often come with a dedicated screening process and direct access to the terminal where your flight is.
It is a luxury though at $65 for a one-off visit or $330 to join + $420 per year. This is something that I have been tossing up with for a year or so now as I could almost justify it with the amount of travel we do. Instead of paying the fees though, I’m giving an alternative a go by using my usual flights and normal expenditure to accrue enough status credits to get access. I’m not going to get into details about status credits here but if you’re interested in how it works, check out Velocity’s Status Credit overview (FWIW, we generally only fly Virgin Australia or partner airlines which makes this possible).
If you fly for work and can convince your boss this is something that will benefit you, I’d highly recommend it.