Breaking Down The Basics: What You Take With You

Urban Explorer

Your roommate is on his way out the door and invites you to go with him to the bar. You stand up and walk to the bar where you meet up with some friends who have an extra ticket to a concert where the band invites you to travel with them to the next tour location where you meet a girl and end up spending the weekend at a beach side cabana. Could you stand up and do that right now with only what you have on you?

I have.


Part of being able to just up and go is having what you need already with you. Sometimes those vital minutes searching for something means you miss your opportunity. The next time someone asks you to go somewhere with them, take a look at the expression that crosses their face when you stand up and say “Okay, let’s go!” – no prep needed.

What follows is a generalized breakdown of some gear that will allow you to wander a city and interact with all of its denizens with ease and comfort.


Wear clothes that are neutral in color, easy to get on and off, and blend into any situation. My clothes don’t attract attention, nor do they convey a set demographic. I could be rich or poor, in college or in my late 20’s, headed to the bar or coming back from a day walking in the woods.

The shirt is a half-zip collared stretchy thing that keeps me cool in hot weather, and warm in cold weather. It washes and dries in under an hour, and compresses up to nothing. It naturally repels liquids, which is great when someone knocks their beer all over you in a bar.

The pants are straight leg synthetic khakis that are also quick dry and water repellent without looking like it. They weigh next to nothing and fold up very small with tons of hidden pockets.

The boxers are Patagonia Capiline Silkweight and, like everything else, dry fast, look good and weigh little.

The jacket is both for rain and wind, and as a place to hold other items. The pockets start in the normal place, but run up the entire side of my body and are big enough to hold a bottle of wine completely inside them. When empty, it folds into itself and can become a small pillow, or a sack to hold other things. There is a built in stow-a-way hood for really bad weather.

The shoes are dark in color, waterproof, and work just fine as hiking shoes or dinner dress. They have Vibram soles, which means I am not going to slip in on wet surfaces, I can hold my own on a trail, and I won’t scuff up someone’s boat deck.

The socks are dark Smart Wool, which dries fast, lasts forever, and wicks the moisture away from your feet to fight blisters and odor.


The phone is an iPhone. Probably the most useful gadget I have ever owned it is my camera, GPS, internet (for finding good places to go, or for meeting up with people) and ebook reader for long trips.

The Leatherman is a Skeletool, which is lightweight and has what I need most. Bottle opener and knife are used the most, followed by pliers and a screw driver for quick fixes. With the knife locked open, the handle fits into my palm to create a good base for a hammer grip should a fight come up. (you never know…)

The wallet is my passport to everything else. Money, proof of who I am, the ability to move freely in a cab, plane, bus or train. I also keep my health insurance and my CPR / First Aid training cards with me as well.

The sunglasses allow me to distance myself from people and avoid eye contact if the need arises (beggars…). They also come in handy the next morning when you have been out all night.

These four items are with me no matter what I am wearing.


The goal is to fit in in any situation. A button down collared shirt  with pressed pants is great at a club in the evening, but if you don’t make it home that night, they look a little rough in the morning. Wearing the above clothes I have swam in the Atlantic ocean then ridden a motorcycle across Costa Rica through a torrential mountain rainforest (literally soaking wet) and into the hot valley on the other side (where the sun dried me in an hour) down to the Pacific ocean, gotten off walked into a nice restaurant, grabbed dinner and a beer then went swimming. No second looks – I fit in everywhere.

When traveling and you stick out, you automatically become a target for others. When I go to Turkey in three weeks, I will have to adapt my clothes to blend in a little more. It helps you get what you want out of the locals.