Friday night I jetted from Chile up to the west coast of the US for a quick trip— 9 days–of business and pleasure in the Napa Valley and Portland, Oregon.  In tow I had only two small suitcases: a Roller carry-on and my computer bag.

Back up to two nights before the trip. I am having drinks with some gringa girl friends at Liguria. Between sips of the Flinchman bubbly, I proposed my intent to travel baggage-less. A kooky silence came over the table. Eyes grew wide. They called it an impossible feat. As my friend Rebecca said, “Shoes alone take up most space in a carry-on. How? How?”. As a clothes horse and self-confessed shoe junkie, I have become sick of overpacking. Half of the things I typically lug with me on these 6,000 mile trips remain unworn. The appropriate occasion is never found. Thus, I have instated Operation Carry-On for these short business trips.

I began to employ this strategy for another 2-week trip to the US in October 2009. My objective was simple. To keep me as far as possible from shopping–mostly in the form of shoes, health food products, magazines/books, and any Apple store. I seem to have some sort of insatiable consumer chip that is activated upon landing in US territory. By calcuting my exact needs, and bringing only the essentials, I had focus. The shopping was greatly curbed; and I felt more free and mobile then ever.

Case in point. In October, I was flying to Chicago via Miami on American. After boarding and on the verge of popping a friendly muscle relaxer for the ride, our pilot annouced, “Folks, we have a gas leak in the right motor”. Eek. Thankfully they figured this one out BEFORE push back and ignition. I deplaned. Estimates for repair we looking like 5-6 hours minimum.  At the next gate, I saw the American Airines Dallas flight boarding. Bingo.  I walked over to the gate and kindly explained the situation. “Since I don’t have any checked luggage, could I be rerouted to Chicago  via Dallas?” Pretty please. Less than five minutes passed. Soledad, the agent, smiled and said “listo”. Ten minutes later I got on the Dallas flight. I landed in Chicago 15 minutes before the Miami connection. Luck? Nope, just Operation Carry-On.

If you are looking to break free from the chains of traveling heavy, overpacking, overshopping, or just avoiding the annoying baggage fees in the US, here are some of my tips to become a carry-on commando. Not only can you do it, you’ll be hooked. It’s such a cinch. Check it out.

1. Choose your clothing wisely

Think about your clothes in terms of the versatility: style, occasion, and colors that you look good in all the time. Also consider if you’re going on an active trip with hiking or going to be tearing up New York’s martini lounge scene. Pack essentially for 4 days and know you will have to do laundry.  I know what you are thinking though, “Wear the same thing?”. Come on, you won’t be seeing the same people all the time and with a few good clothing pieces, you can have up to 6-7 different looks. Don’t forget important things like sun hats, a Belt, combs, a flat purse, scarf, etc.

2. Comfortable shoes

A lot of people recommend only one pair of shoes for carry-ons. I disagree. I think sneakers are a total fashion offense and should only be used for extensive walking, hiking, and gym. Otherwise, bring a smart part of leather walking shoes (I use stylish Dansko black leather clogs that look like boots with jeans). A pair of flip flops is also useful. Remember, the bigger pair of shoes is worn on the plane.

3. Minimal toiletries

You read that right. Don’t bring anything beyond 1 fluid ounce portions. In fact, I usually just buy whatever I need after arriving in small sizes to use on the rest of the trip. Dump anything left over before you leave. That being said, I do take all my make-up, perfume, and silicone for my hair. I cannot look like a frizzy mess on the road.

4. Layer on flights

Wear your heaviest clothing on the plane. They chill these flying tin cans down to Siberian temperatures and give you a weeny blanket. If you have a coat, it will double as a pillow and/or blanket.

5. Ship your purchases home

This is one way for the shopper not to get weighed down by lugging all the purchases. This is especially true with heavy, awkward things like wine, furniture, etc. Or, if you must shop, pack a duffle bag and do it on your last stop to bring a checked bag on the return trip.

6. Know carry-on measurements and weight limits ahead of time

US, Europe, and South America have different sizes and weight restrictions. My carry-on to the US if much bigger and heavier than on the smaller planes doing European and South American routes. Find out ahead of time from your airline. Get a ruler and measure the darn thing. You do NOT want surprises at the airport. I also suggest investing in good luggage. It will make your trip more organized and last longer. Get to know your Samsonite dealer. They can steer you to the more durable options. Buying a good carry-on set changed my traveling life.

7. When in doubt, leave it out

I’ll confess. I almost, ALMOST, put another jacket in that carry-on. My line of thought started with, “well what if it gets really hot”. Then, “what if it gets really cold”. Next, “what if I want to go for a jog”, yadayadayada. That’s my former pack rat self trying to sabotage Operation Carry-on. Beware of this saboteur. When in doubt leave it out. You have to carry it with you the whole time on the road which is more of a pain in the butt than not having it. And if you really need it, hello, unless you’re going to on a far flung Safari, you can probably find what you need wherever you are.

8. Laundry

A lot of people opt for wrinkle-free. I have not personally done this option since I have yet to see high-style come in wrinkle-free materials for business at least. However, I imagine this must be ideal on trips where you don’t need to be primped or in meetings. Certainly my Patagonia shirts are used in tons of travel conditions. I bring shirts and dress pants too. I simply do laundry every 3-4 days where I am staying. While it is an additional travel cost, in exchange you have the mobility to roll.

9. Missed flights and bags no more

Your International flight left late. You landed now and have to go through immigration and customs to make a tight connection but you’re stuck waiting for your suitcase first. This never happens with carry-on. In fact, I usually have enough time to hit Starbucks for desperately needed coffee after a long flight. And no stress about missing luggage. If I could tell you the stories we see with clients coming to Chile…

10. Apple is Carry-on friendly

With all the technology these days, you really don’t need anything entertainment-wise beyond your laptop/Macbook, iPhone, and maybe an iPad. Charge it up ahead of time and you’ll have all you need to keep your trip info at hand and boredom at bay. Don’t forget your chargers either.

Buen Viaje! And go Operation Carry-On.

Thanks to Flickr photographers Stephan Geyer & ksfc84 for the pics. Not sure about how traveling with a kid as a carry-on though…