Carry Less, Travel Better

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I am not the seasoned traveler that many of my friends and colleagues are but I travel enough to have an entrenched routine that works for me.

I’ve always been one to optimize what I carry with me – from a desire to avoid checked-bag fees and skip baggage claim waits. While I’ve never lost luggage I know that its inevitable on a long enough timeline.

This is an outline of what I do and what I have learned to optimize my travel life and is focused on my own experiences. This works for me; ultimately you do you.

Other people have made their own guides and you should look at them too. One under-rated resource is the /r/onebag subreddit.

None of the links are affiliate links.

Start Here

Ignoring clothing, these are the standard items I will always travel with:

  • Carry-on
    • Suitcase
    • Packing Cubes
    • Toiletries
    • Luggage scales
    • Covid test + masks
  • Personal Item
    • Laptop Sleeve
    • MacBook Pro + Charger
    • Power bank + USB-C Cable
    • USB-A and USB-C Lightning Cables
    • OTC Medications
    • Misc: Notebook, pen, US & Irish passports

The Suitcase

I use and recommend The Carry-On from Away. It is a resilient piece of hard-sided luggage; YKK zippers, smooth-running wheels, and a solid handle.

I’m on my second iteration as the handle broke. They replaced it with minimal fuss and at no charge under their limited lifetime warranty. Aside from the speed-bump this one continues to hold-up.

The size works with the mix of international and domestic (US) airlines I care most about, in terms of qualifying as carry-on. In my case thats Aer Lingus, JetBlue, America, Delta, and Qatar Airways.

Exterior measurements: 21.7″ x 14.4″ x 9″ (includes the wheels)

You can compare that against most major airlines here.

The Personal Item

I’ve had the Vertical Device Bag from Moleskin for almost 4 years and it continues to hold up with little visible wear. The luggage strap at the back makes it easy to ride on top of the the extended trolley handle.

I typically travel with an iPad and my MacBook Pro (14″), notebook and other random items. All works nicely within the inner padded compartment. No issues.

At TSA screenings its fairly quick to remove those devices, as well as stuffing phone, wallet, AirPods, and other items briefly into the exterior pouch.

The only minor regret I have is thats it doesn’t easily accommodate my over-ear headphones. It can be packed, but its awkward and makes access harder for other items.

Laptop Sleeve

I bought my current laptop sleeve from SF-based WaterField Designs in 2019 when I got a new computer and needed to change the size. The original one was bought in 2008 and still going holds up.

My preference is the vertical messenger bag with D-rings. The material I got in is the ballistic nylon. I can’t find the exact one I purchased but this is the closest – just not listed in that material.

Vertical + ballistic nylon + magnetic closure + D-rings = Perfect

The version I have is this one with this “Black Ballistic” material. I would just email them. They’ve been very responsive over the years.

The bonus part is that if I take off the shoulder strap it fits into the Vertical Device Bag.

Devices & Accessories

Laptop: MacBook Pro 14″ (2021)

It’s a solid workhorse. I can spin up local WordPress dev environments offline, run a lightweight local LLM with Ollama for quick coverage, and use Second Clock to stay aligned with colleagues in other time zones when I’m remote.

Device: iPad Mini

I have an iPad Mini 4 from 2015 that still serves me well. I like the smaller screen size. Its predominately my entertainment system with a a small set of music and movies saved offline.

Earbuds: AirPods Pro 2

The active noise cancellation means I can actually watch movies and listen to music on the go without full on over-ear headphones.

Transmitter: Bluetooth Transmitter Receiver

I’ve been using the 1Mii Bluetooth Transmitter Receiver so I can use my AirPods with the planes entertainment system. It just works – and you can usually charge it while its in use too. Never be at the mercy of an airlines complimentary earbuds.

Charger: Anker 100W USB-C Charger

Anker’s version is smaller than Apple’s standard MacBook charger and adds three ports (2 USB-C, 1 USB-A). It’s not the lightest, but it’s solid and works.

Power bank: Anker 321 MagGo Battery

No cables, wireless charging. Reliable, small, and does the job.

Cables: Apple USB-A and USB-C Lightning

One USB-A and one USB-C Lightning cable cover me across airports, planes, and hotels, and keep my iPhone 12 Mini and older iPad Mini alive.

Cables: USB-C

The original 240W USB-C Charge Cable for my MacBook, and another shorter one for the power bank and AirPods.

OTC Medications

You never know what to expect so I always travel with a small pill box with the basics:

Melatonin to reduce impact of jet-lag, Zyrtec (antihistamine), Imodium (loperamide), and Advil (ibuprofen).

International

About half my travel is international and then I pack a few extra items.

Travel Plug Adapter: EPICKA Universal Travel Adapter

I have the older version of this. It felt flimsy but it worked solidly. I can’t find a link, but this version supports USB-C and I’ll be moving onto this shortly. Currently a Wirecutter Pick too.

Passports: USA and Ireland

I’m Irish by birth and later emigrated to the United States, which gives me dual citizenship. The ability to streamline immigration on two major continents is a huge win.

Several EU countries also offer citizenship through descent, making it possible for people with the right ancestry to claim a passport. Always do your own research, but at a glance, here are some of the most straightforward options imho:

All The Things

Entertainment

I have Infuse which I use to download movies (obviously public domain) offline onto my iPad.

Self-Care: AeroPress Go Travel Coffee Press Kit

I’ve been using AeroPress consistently for over 15 years for a black, strong, consistent cup of coffee.

Luggage Scales: Airscale Luggage Scale.

No batteries. Easy, small, and light. I had mild anxiety about packing too much and being forced to check my bag, but thats all in the past.

Packing Cubes: Bagsmart Packing Cubes
Set of 6 compression packing cubes compression cubes.

Pill Box: Large and small
Basic, not fancy. I keep the smaller one I keep in my carry-on, and the larger one is for when I’m traveling with family.

Travel gets easier when you cut down to what actually matters. This setup has taken me across the US and abroad without the stress of checked bags or overpacking – whether its for 4 days or 4 weeks. If I forget something outside this list, it’s rarely an issue.

It’s not the only way, but for me, it’s the right balance of minimal and prepared.