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On city sidewalks or mountain trails, the right equipment can spell the difference between ecstasy and agony.

Somewhere between “mountaineering” and “bumbling around like a slack-jawed tourist” is something called “walking.” It is neither a hike nor a self-guided tour, but a semi-directed exploration of new environs, and it may lead through cobblestoned city squares, rocky paths, or chic shopping districts anywhere in the world. Since a hard-core traveler may put in 20 miles in a day on terrain that ranges from mule trails to museums, good gear is essential.

But no tourist wants to look like a tourist. We’ve assembled a kit of technical gear that will camouflage you into any asphalt environment but is tough enough to take to the trails.

The Pack

Neon orange rip-stop? Not for the stealthy hiker. The  Thule Vea Backpack ($130) is meant as an office-to-gym urban bag, so it’s an unobtrusive city black. But it also has burly padded straps (and the trail-necessary sternum strap), plenty of pockets for securing gear, and—most importantly—an expandable interior pocket for dirty clothes and a separate one for a spare pair of shoes. It also has a laptop compartment, which we find is great for keeping your travel journal unwrinkled.

The Poles

Not all walking surfaces are sidewalks or streets, of course, and the best views tend to be at the top of crumbling steps. A set of hiking poles helps you use your whole body to climb and keeps you stable going downhill on ancient goat paths. Because poles are awkward in pottery shops, consider a pair of collapsible ➋ Micro Vario Carbon poles from Leki ($223), which fold up to a packable 15 inches and weigh just a pound for the pair.

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The Shoes

Salewa makes boots that can take you to the top of the Himalayas; luckily, it also makes a shoe that can take you to the café. The ➌ Wander Hiker ($205) is an alpine hiking shoe, but one designed for comfort, with a wide, gummy sole that gives a more stable base and avoids ankle-twisting angles on uneven terrain. Leather makes them easy to clean and polish.

The Bottle

Drinking from a tube is fine for hikers and hamsters; walkers need something slightly easier to fill from a public fountain. The designed-for-travel ➍ collapsible water bottle by Nomader ($22) is sturdy even when empty, small when rolled up, and morally superior to disposable bottles. It can also handle hot liquids and endure being frozen solid.

The Pants

Perhaps because it was designed for climbing, Prana’s stretch Zion fabric couples abrasion resistance with some serious range of movement. It also tailors well enough—in the now-classic Stretch Zion Pant ($85, for him) and ➎ Halle Pant ($85, for her)—for a ramble down a Milan sidewalk, at least if no one notices the small cargo pocket.

The Refresher

Even a leisurely stroll can hike your temperature, and blending in is pretty much impossible when you’re sweating out. Wrap a ➏ cooling cloth by Coolcore ($15) around your neck, and marvel as evaporation helps keep you cool during a walk or stops the sweating afterward. In a pinch, you can use it as a washcloth or for shining your shoes.

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The Map

If you want to stick out in a foreign country, stand on a corner holding a map. With the ➐ Garmin Fenix 5X ($650), you can wear your map right on your wrist. While Google can get your around on the streets, the Fenix pairs GPS and GLONASS satellite reception with topographic U.S. maps, and you can download any other map into it with just a bit of forethought. It also can track your heart rate and step count, monitor the weather, and display a customized face that will fool the city folk into thinking you’re wearing a fancy Swiss chronograph (which might actually be less impressive than this piece of tech).

The Recovery

When your walk is over, and you’ve exchanged your walking gear for a dinner-suitable outfit, you’ve still got many miles of walking to recover from, and there’s only so much red wine can do. You can help your aching feet and calves get back into shape with some compression socks; those by ➑ CompressionZ ($30) are styled in argyle and other patterns that look jaunty peeking out from a pant cuff. Also, try to keep your feet elevated for a bit; you’re going to do this all again tomorrow.

>>Next: Tools for the Well-Equipped Wine Tourist