1 Bag, 2 Weeks: Living out of a Carry-On

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Updated: Nov 29th, 2017

I’ll admit that I used to be the queen of overpacking……I couldn’t fathom going on a trip unless I was totally prepared for any eventuality.

I’d pack no less than three complete outfits (including undies, accessories and shoes) for each day, plus a few extra outfits in case something unexpected came up (formal dinner? No problem! Tea with the Queen? Got it covered!)….and that was just for time spent meeting or socializing with others…..then I’d add in some lounge-wear for watching movies in my room, pajamas, swimsuits, and workout gear (I always have the best of intentions….). And when you have a darling set of five matching pieces of luggage, why not use them all, right?

Ahh those were the days, my friend. Now that most of the airlines charge for checked luggage I’ve been forced to re-think my packing strategy. In recent years I’ve perfected my one bag rule (a rolling carry-on only), and can still get by just fine for as long as two weeks.

Step 1: Check the aircraft

Carry on luggage

Photo courtesy: CarryOnLuggage.info

The type of airplane determines how large my carry-on bag can be (many planes differ in the size of their overhead bins — what fits on one plane may not on another!). In the worst-case scenario (the plane gets changed after booking a flight), if my standard carry-on-sized bag won’t fit, gate-checking doesn’t cost anything (yet) and I can be reasonably sure my bag will still get to where I’m going.

Step 2: Check your itinerary

Check your travel Itinerary

Photo courtesy: TheBalance.com

By reviewing my itinerary I know exactly what I’ll be doing each day, and can plan accordingly for both meetings and down-time. I also ask about the potential for “unexpected events” ….. really, those last-minute opportunities for a formal gala dinner or tea with someone important just don’t crop up that often, but occasionally an impromptu meeting over cocktails or dinner just happens, so be sure to have at least one outfit that qualifies as ‘business casual’.

Step 3: Decide what customization your list needs

What To Pack

Photo courtesy: ZsaZsaBalza.com

I have two ‘starter’ packing lists – one for a business trip, one for a vacation (see below). If I’m traveling for business but plan an extra couple of days for a short vacay, then I combine elements from both lists. To either list I’ll add a few items based on whatever is on my itinerary and expected weather conditions.

Step 4: Choose your fabrics carefully

Fabrics that pack well

Photo courtesy: Reference.com

Avoid any material that will need ironing when you unpack it (that means you, white cotton blouse!). Instead stick with lightweight fabrics that don’t wrinkle easily and un-wrinkle on their own after hanging a bit in the closet. Think cashmere sweaters, lightweight wool skirts or pants, jersey knit dresses, polyester or rayon blends……synthetics with a bit of cotton or linen blended in are good choices for warm climates. Lightweight is key, don’t pack anything bulky (if you can’t live without that cable-knit sweater, wear it on the plane). Many lightweight fabrics can simply be rolled up, making for easier packing, and you can always layer them if the weather is cooler than expected.

Step 5: Resist the urge to over-pack!

Avoid Overpacking

Photo courtesy: RealWorldHolidays.co.uk

When it finally dawned on me that NO ONE CARED about all those adorable shoes I carefully selected to go with each outfit (even though I thought they were applause-worthy), I stopped packing more than one pair of dress heels for work or evening functions and a super-light pair of comfy walkers or flip-flops for anything else….generally I’ll wear those on the plane, unless it’s winter where I’m headed in which case I’ll wear some boots on the plane and pack the walkers.

And it may bruise your ego to hear this, but NO ONE WILL REMEMBER what you wore on a previous day, particularly if you stick with classic pieces in neutral tones that mix and match well. Every piece you pack should be a part of at least two – but preferably three or four – outfits during the week (more on a longer trip).

Tip: It’s amazing how accessories — which are usually small and lightweight, taking up very little space in your bag — can dramatically transform a simple business-appropriate daytime outfit into a dressier evening look. Swap the jacket for a sparkly wrap, the leather belt for a blingy one, the briefcase for a small evening bag, and you’re good to go!

The Bottom Line:

what NOT to pack

Photo courtesy: TheTallestMermaid

Ask yourself this: is it a “will definitely need” item or a “may need it if […]”? Don’t pack any “may need” items that you can borrow (example: most hotels have ‘loaner’ umbrellas if it’s raining) or acquire cheaply wherever you’re going. With this in mind I winnowed my ‘first aid kit’ down to a few band aids and a small blister-pak of Advil, stopped packing an umbrella or raincoat, and stopped trying to plan for unexpected events that just didn’t happen.

All Inclusive Vacation Packing List – this is a printer-friendly PDF (87kb)

Bonus Tips:
  • For a vacation, you really don’t need much clothing beyond your beach/poolwear, a cover-up (and I do mean a full cover-up, not just a little butt-scarf), a pair of shorts and t-shirt, and flip-flops — you’ll spend 75% of your time in these. Pack a dressier look for dinners, as many restaurants have dress codes, but you don’t need a new outfit for each night as you’ll likely be visiting different restaurants during your stay, or possibly ordering room service a couple of times too. If you want to get out and explore or shop, whatever you wore on the plane should suffice.
  • Going skiing and really want to pack that down jacket? Down compresses phenomenally well – just roll it up tightly, squeezing out as much air as you can, then while holding it tightly, put it inside a Ziploc baggie (the smallest size in which it will fit), again squeeze the air out of the baggie, then zip it shut. When you get where you’re going, just shake it out and hang it up – it will re-inflate on it’s own in a short time.

Everyone has their own packing ‘tricks’– what are yours?

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9 responses on “1 Bag, 2 Weeks: Living out of a Carry-On

  1. Harriet

    Good advice, especially about “check the aircraft”. I recently found that my under the seat carry on did not fit well even though it met airline standards.

    1. Trisha Miller Post author

      Yep, that’s sometimes a problem as it seems like the airlines are re-configuring planes to have smaller overhead and underseat space these days – I suspect they are trying to coerce more people into checking bags (which of course they charge for)…and occasionally they’ve switched up the plane I was supposed to be on for a smaller one……gah! But if you at least make the effort to use a carryon that does fit within their required size limitations, you can always do the ‘gate check’ thing, which is still (as of now) free – just be sure to keep anything valuable or necessary (like medications) in your purse or smaller bag that will still fit under the seat!

  2. Deb

    I love your packing suggestions. I have found that sometimes it’s fun to buy from the hotel shops. What’s your experience with the shops at the all-inclusive resorts. Do they carry dressy as well as casual?

    1. Trisha Miller Post author

      Hi Deb,

      I also LOVE to poke around through the shops at the resorts – although I rarely buy because often the prices are higher than what I’d pay at home, still they’re a great option if you’re caught shorthanded for a function where you need a dressy look.

      What I’ve found is that *most* of them are a fun-to-browse mix of necessities (things like sunglasses, sunscreen, toothpaste, OTC meds for that headache or vacation cold you didn’t plan on getting), t-shirts & tchotchkes , and ‘resort wear’, which is to say clothes that are dressy in a tropical fashion — which is about halfway between casual and dressy — usually made of lightweight cotton or linen (which wrinkles, beware!), featuring mostly tropical prints or bright solids, dresses that might be long or short but are more like sun-dresses than a LBD. If you like the style and the price is in your budget, buy something as a souvenir, but if you’re anticipating attending formal events, definitely bring something from home to wear.

  3. Janice

    Hey, I too like Deb like to shop. Thanks for the tip about formal events though because when traveling I like to dine in really nice places and dress for the occasion. My next trip will be in Mexico at an all-inclusive and supposedly very exclusive resort. I will remember to pack my favorite number.

  4. Lois

    My friend recently returned from a three week trip to England. She took a small carry on bag with mostly under garments, shoes and room for gifts. She shopped second hand stores for what to wear while there. Left all behind and returned with special purchases and her original bag. I thought that was a clever way to travel. Of course, someone needs to point out the shops or you will be spending more on clothing than you might paying for a bag.

  5. Nancy

    I love your tips on choosing your fabrics carefully. It really makes a big difference in overall appearance and most of the new fabrics do breath and are comfortable to wear if they have at least some cotton or rayon.

    1. Trisha Miller Post author

      Hi Nancy,
      Yep, definitely choosing fabrics that ‘breathe’ is vital to surviving in the tropics! For me, my number one priority is choosing clothes that don’t wrinkle easily, so I don’t have to iron things…..I just hate doing that, LOL!

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