There's an easy way to ruin a trip, and that's poor packing. Nothing is worse than lugging a heavy bag through a crowded street, except, perhaps, lugging a heavy bag onto a rush hour train. Almost as bad as overpacking is forgetting something essential, be it a tooth brush or phone charger. Nobody needs to be reminded to pack enough clean underwear or toothpaste, but through the years a few items have made their way into my duffel, be it an overnight or week-long trip.
I simply don't have room, or time, for umbrellas. Many rainy cities are also windy cities, which render an umbrella not only useless but potentially dangerous. Never mind how ridiculous you're going to feel carrying around an umbrella when it stops raining. That's why I always travel with my trusty Patagonia rain jacket. Yes, the bright yellow is quite garish, but the visibility is nice for cycling. Most importantly, even in a torrential downpour your body is going to stay dry. As an added bonus, it takes up as much room in my bag as a pair of socks?
We've all experienced it: you set out freezing cold, but by the time you arrive at your destination you've worked up a sweat and are carrying your jacket. That hasn't happened to me since I discovered nature's most versatile fabric: wool. Wool magically always keeps your body at the right temperature. Whether you're freezing cold or starting to work up a sweat, the temperature regulating and moisture wicking properties of wool ensure it's exactly the material you want on if you're on the move. New Zealand-based Icebreaker has some of my favorite wool clothes, including base layers and hoodies.
Your passport is your lifeline when traveling overseas, which means your should protect it in style. Forget those ridiculous lanyards that American tourists tuck inside of their shirts, bulging like some strange tumor. First of all, no one is trying to steal your passport. Secondly, if someone wanted to steal your passport they now could do that very easily. They see exactly where it is and there's a rope attached to it they can just pull. A classic leather passport wallet was good enough for your grandparents, and it's good enough for me. There's probably a dozen at the nearest antique store.
Universal Power Converter
Canada, Australia, and the United Kingdom might share a common language, but the three countries have three different power sockets. For better or worse, modern travel depends on electronic devices, and few things are more stressful than not being able to charge your phone or laptop. A good universal converter will help you be prepared for where ever your travels take you.
There's two errors to be made regarding travel photos. One, is to be caught lugging a camera bag full of gear you probably won't use. Unless you're a professional photographer on the job, you don't need to have a 35mm and a 55mm lens at your disposal. That being said, it took you a long time to finally scratch that destination off your list, and you probably should capture the moment with a higher quality image than just a cellphone picture. Contemporary mirrorless cameras are capable of producing some truly stunning images at fairly reasonable prices. There's some great ones from Sony, Canon, and Lieca, but I'm partial to the Fujifilm x100 series. Intuitive controls and a classic aesthetic make shooting with my x100F a joy. Its small profile means I'm willing to take my camera out in places a SLR would feel intrusive, and an iPhone just isn't going to cut it.
I know conventional wisdom would teach you to wear some ugly but comfortable slip-on shoes when flying. But conventional wisdom is wrong. You should be wearing some big, sturdy, well crafted boots. The reasoning is simple: 1. you should always have a good pair of boots. and 2. You don't have enough room in your bag for a pair of boots. My Red Wing Iron Rangers are sturdy enough to handle a Panamanian rainforest, but classy enough to wear to a nice restaurant with a quick polish. This is a boot your grandchildren will inherit one day.
A Good Book
Even though you can now purchase internet on most flights, I relish traveling as one of the few times one is allowed to disconnect from the grid. Although a Kindle book would be the smarter decision when it comes to baggage allowance, there's something irreplaceable about having an actual book with you. One of my favorite books to recommend to any traveler is Matt Gross's The Turk Who Love Apples. The book chronicles Gross's experience writing The New York Times column The Frugal Traveler. From his first awkward steps in another culture, to those transcendent experiences that keep us coming back for more, Gross's book offers an engaging, laugh-out-loud hilarious, and occasionally sobering perspective on why humans travel.