How To Pack For Warm-Weather Urban Travel


No checked bags, please!

So, I drafted this post on the plane back from my 2 week trip to California (San Francisco, LA and San Diego), but I never got around to putting it up here. It's as close as I can muster to a comprehensive breakdown of my packing style for the trip–complete with things I'd add, subtract and why!

Check it out:

9 things I wished I had with me:

  1. Bathing Suit – Three times I had a chance to go swimming, and didn’t because I would have had to purchase a suit. A suit would not have taken up much room in my bag, and would have paid for itself in fun.
  2. 2nd Charging Cable – I used my Apple devices constantly along the trip, and so recharging was a regular routine. I chose not to bring a duplicate charger for the iPad Mini and iPhone. On second thought, bringing an extra lightning cable would have taken up minimal space, and allowed me to charge all three devices at the same time by using my computer usb ports. It would have saved a ton of time and aggravation.
  3. Q-tips – I used earplugs and headphones a lot on the trip, and totally forgot cotton swabs for my ears. It was uncomfortable, and the cost of buying the “travel packs” for these is disproportionately expensive compared to packing a few in a sandwich bag.
  4. Some kind of solar charging pack – These are easy to find in airports and electronics stores or online. Some are built into backpacks. In a sunny place like California, a solar charge would have been practical, and allowed me to blog, video, or chat nearly anywhere without fear of losing charge.
  5. Travel towel – If I had been staying in hotels or even AirBnB consistently, this would have been optional, but it was really a necessity when staying with friends and couch surfing. If I had gone swimming, this also would have come in handy.
  6. Versatile jacket – In Northern California, the weather was mild in daylight, then by 5pm just a bit windy, and chilly enough to warrant a sweater or jacket. I had a single heavy cardigan with me, but it was very unique in style and did not work as a layering piece all the time. I ended up buying a tweed blazer, which served me well, but I had to carry it around because it didn’t fit in my pack.
  7. Flat or roll-up water bag – I found myself buying bottled water often, but I had access to filtered water taps many times during my trip. A smarter, greener option would have been one of those “water bottles” that lays flat.
  8. Multi-tool – Several times during the trip, I needed scissors, a spork/spoon/fork, and a cork screw. A simple approved multi-tool would have done the trick. I improvised, of course, but you know… simplicity.
  9. Pre-loaded work materials – I got cavalier about being able to bring most of my electronics with me, therefore I didn’t prepare my materials as neatly as I could have. I advise taking time to download and prep reading, writing and work materials so that they are available to you on and offline, and choosing which devices will be used for what. Take a look at storage space and decide if it’s necessary to have extra memory sticks etc. I was relying on Dropbox and Cloud storage a lot, but I wasn’t always online. D’oh!

4 things I wished I’d left at home:

  1. Thin Sweater – I always favored the cardigan or jacket for layering purposes. This stayed in the backpack.
  2. The travel pillow and blanket – Totally unnecessary except on the flights. I could have used rolled clothing to do the same job. This ultimately caused me to carry a bulky third bag with me everywhere.
  3. Whole jar of vitamins – Silly waste of space. Could have packed 13 days worth in a small baggy.
  4. Apogee One microphone – I never used this once, and for the camera work that I was doing (interviewing people and doing panels) with my iPad and iPhone, it wasn’t really necessary. I definitely needed a smarter solution, but the One was a delicate and kind of clunky option for use with iOS devices. Mind you, it’s a tiny and impressive unit by any normal computer recording standards, and only took up the space of a small toiletries bag, but I could have been even more minimal.

3 things I will totally upgrade on the next trip:

  1. Sandals: I brought a pair of simple 3-dollar flip flops from home, which I ended up wearing a lot once I got into the warmer weather. Thing is: this is one of those cases where I could forgive myself for going “disposable”. I could easily have picked up an identical pair at any dollar store or pharmacy, then chucked them before the return flight, saving space. They took a beating on the trip, and are now so worn out, they’re barely worth the space in my luggage on the return flight. The benefits were that they’re cushy for walking, I didn’t care about them getting damaged or lost, they are washable, and they pack totally flat. How & why I’d upgrade: I’ve decided that packing sandals is a must in nice climates, but it’s worth it to invest in better quality to maximize form and function. Because I had a wide range of activities and occasions to attend, it would have been nice if these sandals were classy/dressy enough to complement a dress, while still working with jeans or yoga pants. A high-quality leather sandal that can be cobbled, either with a rubber or leather sole, and sufficient straps to stay on your feet when walking long distances would be ideal. I noticed that the cheap rubber absorbed (by which I mean retained) odor and caused my feet to sweat more than a leather sandal would. While leather could be a wee bit heavier in the luggage, it would still pack flat, and balance out in flexibility.
  2. Back Pack: I was very happy with my Incase commuter backpack, considering I didn’t buy it with travel in mind. It’s made of futuristically light material. The empty pack's weighs about as much as a small coffee; perfect for keeping things light. It was designed to hold a few bulkier belongings, a 17” laptop, a tablet, and whatever smaller items might fit in the front pouches and pockets. I managed to travel for 12 days with this bag, and a thin leather satchel, plus a paper thin market bag which held the travel pillow, blanket and whatever I was too lazy to fit back into the pack or satchel. How & why I’d upgrade: Having hands free is a requirement, therefore it’s worth it to invest at least $100 on an ergonomic pack or piece that lets you maneuver freely, even when you have everything with you. Think about it… what will you really do when traveling? Take pictures, have a cup of coffee, swipe in and out of train stations, navigate uneven terrain, get in and out of airports and taxis with ease, hold an umbrella, shake hands, read a map… Doing this with three bags is a serious drag, and dramatically increases the risk for mishaps, or worse, losing track of stuff. I am considering a bag by Chrome, SeaLine or Timbuk2 for future trips.
  3. Travel Temperature Trifecta: The TTT hahaha. I have a strategy to improve several items in my lists of things I wished I did or didn’t take. Uniqlo, a trendy and inexpensive Japanese clothing brand sells ridiculously lightweight “down” vests and jackets which are paper thin, nicely structured, colorful and, best of all, can roll up and be stored in the small included pouch. Instead of the thin sweater I packed (and didn’t wear), and the thick cardigan I packed (and wore sometimes), and the tweed jacket I had to buy, I would opt for a thin cardigan/button-down sweater for layering, and one of these Uniqlo down pieces as a jacket. This option reduces 3 pieces of bulky clothing to two, where one actually stores as a pillow… You see where I’m going with this. Omit the travel pillow. Then, I’d replace the travel blanket with a fast-drying lightweight travel towel, which if properly dried, could serve as a travel blanket on the plane.

3 most useful things I packed:

  1. Simple leather ankle boots. These boots feature a flat, rubber sole & leather insole. They are thin brown suede, and lace up. While just as comfortable as sneakers, they look a bit dressier. I packed some Scholl’s insoles, in case I was going to do a lot of walking or standing, but most of the time they were unnecessary, and I left them out to keep my feet cooler in the mild weather. I was able to wear these with jeans, skinny dress pants, a skirt, and a dress. Because the suede is very pliable, the boots could fold down and pack nearly flat, when not in use.
  2. Wrinkle-free dress: For women, this is invaluable. What I brought was a simple pull-over halter dress made of slightly stretchy wrinkle-free fabric. It could be rolled up for packing, and you’d never know it. This dress has a shirred design through the waist which creates a slimming effect while being comfortable both standing and sitting. The skirt comes down to the knees and has a very slight flare, making it appropriate in any social setting, and easy to move around in. It also has padded support around the bust line which allowed me to optionally skip the bra. With accessories, this solid color dress can go from classic to bohemian to beachy to formal. To me, this is a packing must-have. We are talking one single piece of clothing and you’re fully dressed for any occasion, saving perhaps serious sports activities. Though I packed for California, a heavier gauge material dress could work the same in winter, paired with cling free leggings.
  3. IKEA freezer bags: Ikea sells a box of 4 different sized thick gauged, zip-up freezer bags. They are durable, color coded and see-through. I have investigated a number of expensive options for the trick I’m about to describe, and honestly… for under ten dollars, you can do exactly the same thing. I use these for the TSA required clear toiletries bag (1 quart or less), but I also pack my underwear and groups of smaller items/clothes in these. By pressing the air out of them before zipping, they make faux “compression” bags. Then I pack a fresh stack of 4 or 5 in varying sizes. As the trip goes on, I use them to keep dirty laundry separate from clean clothes, and I store whichever shoes I’m not wearing in another. Food goes in a third. Documents go in yet another. The bags slide in and out of luggage smoothly, and can easily be labeled with a marker. With this system, I always know where things are, clean/dry things stay separate from dirty/damp things, and my backpack stays odor and pest free.

Cost-saving snack purchases:

These things all packed flat, and weighed very little... In transit, or in odd places, I never got "hangry" because I had these handy treats to tide me over.

  • Mission flour tortillas
  • Instant Oatmeal Packets
  • Starbucks Via Packets
  • Instant Miso Soup
  • Clif Bars