7 Tips for Packing a Carry-On From an Adventurous Globetrotter

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Checked baggage is a gimmick. Simply to get your belongings where you’re going, you have to pay extra fees, wait in extra lines, and send extra prayers to the travel gods that your belongings will even make it to your destination. Darrell Wade, founder of Intrepid Travel, the world’s largest adventure travel company, has shifted from dusty backpacker to jet-setting CEO taking meetings in New York and Sydney, but one thing hasn’t changed: Wade never checks a bag. “Be it a few days or a couple of months, I only ever have a carry-on these days,” Wade says. Here are his go-to tips for packing everything you’ll need.

1. Make a list. Then stick to it.
“My list includes what I’m wearing on any given day so the ‘what’s in the bag list’ is one item less of each item.”

  • four shirts (“The proportion of long/short sleeve depends on weather balance; my upcoming trip to Australia is three short-sleeve shirts and one long-sleeve.”)
  • one pair jeans and maybe one pair of chinos
  • one jacket or sweater, depending on the trip (business/leisure balance) or weather (neither if largely warm weather). This item is usually worn rather than packed.
  • one pair of shorts
  • swim trunks
  • four pairs of underwear
  • three pairs of socks
  • one pair of shoes
  • one pair of flip-flops

2. Get shoes that can do both.
“Shoes need to look OK in a more formal setting, but be able to pound the trails when you’re off exploring. I always take either Rockport or Camper shoes.”

3. Make the most of your carry-on and personal item.
Most airlines allow you to bring one carry-on piece of luggage (like any of these rolling suitcases) and a personal item. That means you get two bags to bring your necessities along in. Keep clothes in your carry-on and maximize your use of the “personal item” by bringing along a small duffel, a backpack, or a briefcase. You can use it to carry your electronics, work supplies (if it’s a business trip), toiletries, and miscellaneous items. “My sundry items usually include a hat, bathers (swim trunks), phone, charger, adapters, sometimes a micro umbrella,” Wade says.

4. Wear and wash. Repeat.
Wade doesn’t pack any more than four shirts and two pairs of pants for any trip — whether he’s going to be gone over the weekend or the next few months. That means at some point, clothes are going to need a little refresher. Most hotels have laundry service, or if you’re not staying in a hotel, utilize local laundromats for cheap self-service or drop-off services. Or, if you’re in a pinch for time or money, do it the Darrell Wade way. “I wash my clothes myself in the bathroom,” Wade says. “It’s faster, more reliable, and I save a small fortune. I make sure all the clothing I bring is fast drying.”

5. Put everything on the cloud for business trips.
“Digital access is vital for me. I’m the CEO of a global adventure travel company and so I need to be available wherever and whenever. Having everything in the cloud means I can live off my phone and not have to lug technology or paper around like I used to. It’s so liberating.”

6. Don’t try and hack the system.
When it comes to size and weight regulations, it’s best to play by the rules. “I pretty much stay within the rules to start with, so it’s not really an issue,” Wade says. “My attitude to travel is to be as flexible and agile as possible — it just makes for a better experience. If I’m not weighed down by bags and stuff, I can more easily make plans, change plans, jump in a car or train, or do whatever takes my fancy at the time. Airline weight rules are an assistance in this philosophy rather than a hindrance. It helps keep me honest to my travel philosophy.”

7. It’s better to underpack than to overpack.
For most trips, packing light shouldn't be a problem because you can almost always buy something locally if you need it. “I tested this a few years back when I had a couple of weeks in central India,” Wade says. “I assumed it would be warm so took nothing but a couple of T-shirts and some shorts. It was actually freezing cold, and at six-foot-seven, I could hardly walk into a shop and buy some jeans. So instead I bought a shawl thing that all the locals were wearing. Apart from keeping wonderfully warm, I was able to fit right in.”