How to travel like a pro

Do you enjoy lugging a massive suitcase over the cobblestone streets of Europe?  Do you love waiting at the airport for your checked bag? Or waiting in huge lines to check your baggage at the airport?

Perhaps you’ve noticed: business travelers NEVER check a bag.

Everything they need for a 1-3 week trip can easily fit in a relatively small carry-on sized luggage.  “How,” you might ask?

Don’t pack like this

I’ll keep this short and sweet:  I travel for work, and as a result, I think a lot (perhaps a little too much) about what to pack.

I travel mostly for business (touring with Canadian Brass about 60-75% of the year), but most of the techniques and gear I suggest below came from what I learned through ultralight backpacking and camping.

Know where to look: Backpackers and Hikers Know the Best Lightweight Travel Gear

I test my methods and gear a lot before I recommend it, so I can say with confidence that making the simple upgrades below will turn you into a travel pro.

One thing… This is important!!!

I HATE traveling with dirty clothes (and you should too).

If you currently pack enough clothes to wear a different outfit each day, you are missing out on the most enjoyable part of traveling: FREEDOM.

It may sound cool to have your entire wardrobe with you, but you’re soon lugging around a huge suitcase filled with dirty laundry which is not fun. Trust me. Nothing beats traveling light: a small carry on, plus maybe one personal item (which in my case is my ultra-compact trumpet case) is all you need.  Here’s how:

  1. Pack only 3-4 pairs of socks and underwear. Clean the pair you wear each day (this only really works with quick drying items such as those listed below – they dry in just a few hours). Especially when you’re hitting a different city each evening this method is a life saver, you never have dirty clothes in your bag, and you can bring a very small suitcase.  FREEDOM!
  2. Pack only 2-3 button down shirts and clean as often as needed. Again, the ones listed below dry very quickly and are wrinkle free so they don’t need ironing/steaming.
  3. You do NOT need more than 2 pairs of pants.  Unless you’re rolling in the mud, you can easily keep 2 pairs of pants in rotation and stay clean as a whistle.  Just make sure you have a Tide Pen handy just in case you do spill on yourself (I once spilled an entire glass of red wine on my white pants 3 hours into my 14 hour flight to Japan–fun times).

Finally, here is some essential clothing items for ultralight business travel:


I have 2 favorites button down shirts:
  • This button down shirt by Ministry of Supply is one of the best shirt for business travel.   You can wear it to the most formal events but also wear it all day as it is SUPER comfortable (it’s very stretchy–the company’s CEO even ran a half-marathon in it).  The best part:  you can wash it and it will hang dry within a few hours.  No ironing, ever.

This is Ministry of Supply’s CEO running a half marathon in his company’s super comfy clothing

  • These dress shirts by Brooks Brothers are also great.  They aren’t stretchy nor do they dry fast, but they are some of the best looking wrinkle-free dress shirts, they always stay crisp and don’t lose shape in a traditional washer/dryer cycle.

    Smartwool UltraThin Hiking Socks are the first step towards travel freedom.  Backpackers use them because they don’t smell bad even after many days of backcountry abuse and they dry quickly.  These are technically “liners” which means they are very thin, about the same as most dress socks. They are also very comfortable, simple (plain black is what I usually use), and when washed will air dry in just a few hours.
    – Pros: comfortable, don’t smell, dry quick, pack very light/small
    – Cons: none


    These Airism Boxer Briefs by Uniqlo might just change your life as much as the Smartwool socks listed above. They look great, are super comfortable, pack ultra small, and dry quickly.
    – Pros: Cheap, light, dry very fast, comfortable, packs very small/light
    – Cons: None
    Many pro travelers recommend the Exofficio Boxer Briefs, most notably NY Times best-selling author, ultra-blogger and serial entrepreneur, Tim Ferris (he wrote 4-Hour Body, 4-Hour Workweek, 4 Hour Chef, and Tools for Titans — all HIGHLY recommended).   Personally, I prefer the Uniqlo Airism’s listed above; they’re much cheaper, I find them more comfortable, and they dry quicker, but they are both listed as you may prefer one over the other depending on body type.  For women: check out Calvin Klein’s Invisible Hipsters
    – Pros: may be considered more comfortable than Uniqlo Airism for certain body types
    – Cons: pretty expensive, more material (multiple layers) hence slightly more difficult to clean (rinsing takes more water/time/effort/etc.) and longer drying times


    This jacket compresses to fit in your pocket.  I sometimes put it in the bell of my trumpet.. it’s that small.  It is also warm and stylish, it works great alone or can be layered with a sweater (I usually wear a sweater and this jacket in temperatures as low as 49°F until I need an additional layer or a warmer coat).  This jacket also makes a great pillow — I use it as a neck pillow, for lumbar support or as a blanket on flights.

    – Pros: ultra light, perfect for layering, very warm for it’s size, great value
    – Cons: none
    What do you think?  Is there a piece of gear or advice you think I missed?
    Let me know in the comments section below.