I travel a lot. Last year I spent 155 days away from home (that’s 42% of the year!) I don’t do a lot of carry-on-only travel and that’s mainly because I’m a pack rat and I love buying things to bring home or bringing presents to people, and most of my flights have free baggage allowance. I actually just bought a new carryon suitcase and I’ll be experimenting with doing carry-on only on some of my shorter trips.

So I usually check one or more bags and bring my Timbuk2 WordPress messenger bag (don’t you love the fake brown leather?) or my SwissGear backpack as my carry-on. A lot of my travel is flying, but this bag is close to the same for train travel, or even a road trip.

Let’s look inside!

#1. An Apple. Breakfast – the first thing to go. I have a lot of early morning flights and I like to eat something once I get to the airport (much like my ritual of getting an espresso post-security-check). If I’m traveling inside the EU or inside the US, I usually pack 2 or more apples so I can have one when I arrive at the hotel or wherever I’m going. Sometimes it’s dates + peanut butter, or a yogurt. I also pack food in my suitcase when I travel, don’t you?

#2. Cables and electronic stuff. In here I have several short cables for iPhone, iPad, micro and mini-USB, my headphones with mic (so I don’t need to bring a separate headset for conference calls), an ethernet dongle for my MacBook Air in case they don’t have wifi, a USB adapter with US plug, and one with EU plug (I bring both no matter my destination, in case I get stuck somewhere), and an Android phone, unlocked, so I can use different SIM cards. The zip bag is one of a set of Travelon mesh plastic bags (red ones, too!), also used in #6, I use for anything and everything – I’ve gone through 2 sets.

#3 A scarf. I always travel with a scarf, even in the summer. This scarf is lightweight but it’s quite big so it can double as a blanket in a cold airport or airplane. Linen scarves work, too.

#4 Medicine bag. Flying exposes you to a lot of germs, and while I don’t relish taking medicine, I like knowing I have some with me, and from the brand names I’m used to. I know a lot of medicine you can find anywhere, but keeping a couple of pills on hand, from a brand I trust, saves me that emergency trip for myself or for a friend. I carry Tylenol (headaches/fever), Advil (muscle pain), a decongestant, cold/flu tablets, antiacid, Emergen-C (basically Vitamin C + some extras), antibacterial salve, and some antibacterial wipes (I’m not a big fan of antibacterial sprays/soaps for daily use but I think it’s good to have on hand for cuts).

#5 An umbrella. I never know what weather is going to be like where I’m going, or most importantly, what I’ll come home to. It helps to pack a small one and I can always buy a big one if I need to. That umbrella fits in my day purse if needed. It’s a Totes Micro umbrella.

#6 More snacks :) I always have some raw almonds on hand for when I get extra snacky – I can bring better choices and save money vs. buying at the airport. I usually stick some dried fruit (like dates), a protein bar like NuGo or Lara Bar, packets of Justin’s Peanut Butter, and I also usually pack some chocolate of some kind so I don’t stop and buy peanut M&Ms. I stick extra peanuts or pretzel packs from flights I’m not hungry for as I sometimes want them later. And I usually have at least one packet of Starbucks VIA (instant coffee) so if I need a caffeine fix somewhere…I have it. On this particular trip I got an extra pack of Pocket Coffee and some Venchi Caffe snacks after check-in.

#7 Collapsible water bottle. This one’s a Platypus bottle. I drink a lot of water daily and definitely when I work out, and I like knowing I can fill up and carry with me as needed, and roll up when finished. I like to fill this up post-security check or I fill it up on the plane and ask the flight attendants for a refill when needed. If I bring my backpack, which is a bit bigger, I often bring my Kleen Kanteen stainless steel refillable bottle, too. When I’m staying in one place for a while, I’ll buy big 2-liter bottles of water and then refill the smaller one as needed for on-the-go.

#8 My actual daily purse (small, right?) by Furla (I have a few of these, it’s a problem I openly admit to). This is the purse I actually use day-to-day in Italy.  When I get to my location, I can leave most of the other contents of the carry-on bag in my hotel and just take my purse to go out for dinner or to run out and pick something up. In this I have the usual: wallet with cash & credit cards, business cards, my iPod nano (I love listening to music everywhere & I have a special downtempo mix for when I fly), keys, a pen, my iPhone, and some makeup: powder, mascara, lip gloss, and a few lipsticks.

#9 My Moleskine notebook or planner. I need to travel with something to write in, whether I’m planning something or need to take notes on something. I always use a Moleskine - the one pictured is a 2013 weekly planner but my go-to favorite Moleskine notebook is the square reporter pocket. There’s often a lot of waiting in travel (on the train to the airport, waiting to board, waiting for takeoff), and the few times I’ve forgotten it, I’ve really regretted it. There’s a Moleskine pen attached which you can’t see clearly.

#10 My iPad. I love to read and being on a transatlantic flight gives me an opportunity to read uninterrupted since I rarely sleep while flying and the iPad’s battery lasts forever. I also like to load up my iPad with movies just in case the inflight selection isn’t great. This is an iPad 1 and I’ve had it for almost 3 years now, so I’m looking at upgrading to a lighter version – the iPad Retina or the mini are on my radar. If you’re asking, why not a Kindle? While I definitely buy Kindle books (I published two Kindle books myself), mainly I like the multitasking of the iPad and I’ve been reading ebooks for 7 years and on backlit devices for almost the entire time (it doesn’t bother my eyes, and I like to read at night, too).  To find out more about what I think about ebooks, check out What are ebooks? Advantages and Disadvantages of Electronic Books on my tech site, When I Have Time.

#11 Passport and Italian permit of stay. Pretty much need these to get anywhere. One of the first things I put in my bag. I have another 5.5 years left on this passport and I only have 4 pages without any stamps!

#12 Foreign currency coin purse. I travel often enough to the US and London that I keep separate, dedicated coin purses for those currencies, SIM cards, and subway/Tube cards. When my flight lands and we’re taxiing on the runway, I just switch out my Euros and change into this purse and move the other currency to my wallet. The coin purse is Coach (and it was on sale!)

#13 Eye glasses. While I don’t need them to see normally, I do need them to use the computer for any longish period.

#14 Flip & Tumble 24-7 bag. One of my favorite things – I wrote about Flip & Tumble bags way back in 2007 when I first discovered them, and over the years I’ve bought and gifted many. This little ball becomes a shopping bag that I can sling on my shoulder. It can become a gym or beach bag, it can carry swag, it can hold my shopping, or it can become a sort of purse as I put my smaller purse in there with other stuff. Rolled up I can fit it into my day purse (#8) and it can hold up to 25lbs. Highly recommend, and it comes in a lot of colors!

#15 Miscellaneous: Tissues and wet wipes. I never travel without these, and I love that in Italy they sell these single-packs everywhere you go. If I don’t have room to carry a full pack of tissues with me, I often stick one or two loose tissues in my day purse or jacket.

What you don’t see and variations on this bag: my microfiber cloth to clean my various screens (I always realize how dirty they are when I travel), and my 13″ MacBook Air and power cord which fit in there, too. Sometimes I may bring my Canon 7D with the 50mm f/1.4 lens with me as well, and rearrange or remove things to make it fit.

What would you add differently? Is there anything you’re surprised to see?

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