How to Pack for a Multi-Season Trip (Without Checking a Bag)

For three weeks in January and February 2023, I took a trip that started in San Antonio and visited, in order, Niseko, Japan; Tokyo, Japan; Queenstown, New Zealand; and Sydney, Australia.

The Challenge

This trip included skiing in Niseko, Hokkaido, Japan; business meetings in and around Tokyo; a conference presentation in Queenstown, New Zealand; walking, hiking, boating, and a wine tour around New Zealand; and a brief stop in Sydney before coming home.

Since the trip was in January and February, that meant I needed to dress for four separate climate/activity combinations:

• skiing (9–28°F/-13–-2° C) in Niseko
• business in Tokyo (29–56°F/-2–13°C)
• business and touring in Queenstown (46–84°F/8–29° C), and
• walking in Sydney (66–73°F/19–23° C).

Temperature range: 9°F/-13°C and snowing to 84°F/29°C and sunny.

Activities: skiing, walking, hiking, meeting, presenting.

Luggage permitted: the same Minaal Carry-On 2.0 I use for every trip I take.

Bonus challenge: Jetstar has a hard 14 kg/31 lbs limit for carry-on luggage, even if you pay them more (which I did; the default is 7 kg/15 lbs).

Concessions

I should pause here and mention two decisions I made at the start of this trip that made it a little easier than it might have been:

1. I insisted on taking my ski helmet, but I left my ski boots behind. In retrospect, I did have enough room for the boots, but only because...
2. I actually took two backpacks; the Minaal and an Osprey Daylite Plus. The Minaal Carry-On is too big to take skiing or hiking comfortably, and I don't own a Minaal Daily, although I'm not sure how good it would be as an active daypack either (hey Minaal: feel free to send me one to find out).
   That meant that, in a pinch, I could use the Osprey as an overflow carry-on, which came in handy when I decided to bring back a ton of mochi for my wife and coworkers. I don't count this as cheating, because I packed the Osprey inside the Minaal for the outbound leg of the trip.

Packing List

I'm not going to post an exhaustive packing list, partly because I didn't take any pictures as I was packing. Instead, here are the items that were (or would have been) hardest to pack and what I did about them.

• Ski helmet—strap to the outside of the Carry-On. Across four countries, three continents, and eleven airports, zero people questioned me about it.
• Ski goggles—like the helmet, goggles are incompressible. Shoved it in the top of my Carry-On after packing everything else.
• Ski pants and ski jacket—fold the pants Marie Kondo-style (in half, half again, then thirds) and wear the jacket. It was going to be cold (29°F/-2°C) when I landed in Japan anyway.
• Business suit—my travel suit is the Bluffworks Gramercy in Gotham Grey. Yes, it's expensive. Yes, it's 100% worth it for a wrinkle-free travel suit I can wear basically anywhere. No, nobody's going to mistake it for something off Savile Row.
• Dress shoes—the Achilles heel of my packing life. For business events where brown shoes are appropriate, I have excellent Rockports that double as walking and even hiking shoes. But my black dress shoes are absolutely not ideal or even comfortable for travel.
  I wore them anyway and stuffed some slip-on Chacos in my bag.
• Everything else: merino wool base layers (top and bottom), undershirts, long-sleeve hiking shirts, and socks; ExOfficio synthetic performance underwear; bathing suit for the onsen; ski gloves and glove liners; various electronics (laptop, phone, GoPro, outlet adapters, and chargers and cables); sunglasses; and a Dopp Kit round out the entire packing list.

The Secret

To the greatest extent possible, don't bring any single-purpose items.

That's it. That's the entire secret.

Some things have exactly one purpose: ski helmets and ski goggles don't really double as hats and glasses when you go from northern Japan to New Zealand in the same season.

For everything else, make it double up. Here are some examples:

• Good socks can be worn with all kinds of shoes or by themselves. In this case, I wore the same socks in ski boots and dress shoes. (Don't worry, I didn't wear the socks with the Chacos. At least in public.)
• Your hiking shirt doubles as an extra layer while skiing. So do your undershirts.
• A good top can be worn in all kinds of situations. For men, a performance button-down shirt can be worn pretty much anywhere, from the board room to the backcountry to the beach. Just remember to remove the tie when entering adventure mode.
• You should aim to take exactly one pair of shoes on any given trip. This is hard, and it's harder for women than for men. But think across all the activities you're planning or likely to do, and choose shoes that you can wear on the airplane, in the hotel, on the road, on the trail, in the restaurant, at the meeting or conference, and on the beach. Okay, that last one's impossible; get some slim, cheap, slip-on pool shoes and slide them into some leftover space in your bag.

The Other Secret

Just like nothing you take should be single-purpose, nothing you take should be single-use either. That means everything needs to be odor- and stain-resistant, easily washable in a hotel bathroom, or both.

You almost never need more than a full week's worth of clothes for a trip of any length, and you should be re-wearing most of those clothes during the week.

On this trip, I took three button-down shirts, three undershirts, four pairs of underwear, and four pairs of socks. That meant I never wore anything more than twice before I had a weekend to do laundry. (For me, laundry while traveling involves the hotel sink, some Dr. Bronner's soap, and a towel. Your mileage may vary.)

Take It Slow

Travel is almost always expensive—plane tickets are just the start. The Hedgehogs have spent years building up wardrobes that fit all these requirements, and we're not done.

The total cost is pretty high.

But the freedom enabled by grabbing a single backpack for each of us and hustling through an airport, an office building, a forest, or a ski slope makes it all worth it.