(Andy Gregory navigates a beachfront African city where savory local wine is free-flowing and you might get robbed on a hike) It’s just before 5am a few days after Christmas when a Cape Town tour guide named Rob is held up by two thieves wielding broken beer bottles. Rob, a tall, rugged South African in his 40s, is standing 50 meters away from the entrance to the downtown Holiday Inn where he’s picking up two hikers from Europe for a guided sunrise trek up Cape Town’s iconic Table Mountain. Rob has led visitors up the mountain for over a decade, sometimes twice a day, so he’s well prepared. He has a large backpack of supplies, sturdy boots, walking sticks, and the bravado of a true South African adventurer. His rules for “walking about safely” in the wilderness include “leaving behind valuables like wedding rings and passports” and letting loved ones know where you’re going. Oh, and pepper spray, not to ward off wildlife, but other humans. “We strive to minimize risks,” he says in a lengthy text message to hikers the day before, along with a list of things to bring: -best walking/hiking shoes -hat, sunblock for the African sun -long-sleeved shirt to prevent bush blisters -windbreaker, weather can change quickly -water Once at the foot of the mountain, Rob provides hikers with snacks, snazzy headbands, and one bottle of pepper spray each to keep around their necks. A long-time resident of Cape Town, Rob has used pepper spray against potential robbers more than once, including the two men outside the Holiday Inn. Unfortunately, he says, South Africa grapples with complex political and social problems he’s seen first-hand his whole life. Fortunately, Rob is uninjured in the failed Christmastime robbery attempt. It lasted just seconds because he had pepper spray. He suspects an Uber driver set him up, but can’t be sure. Rob uses Uber to get around everyday. Uber in Cape Town is fast and cheap. Short inner-city trips cost as little as $2USD. Despite what happened outside the hotel, Rob is undeterred from using Uber or showing off his city’s crown jewel. He decides not to tell his European guests what happened to avoid unnecessary panic, and they go ahead without incident. I only learn about his story the day after, on our up-hill walk together. Hiring a guide to traverse Table Mountain isn’t mandatory but recommended. The hike itself is steep. Trekkers can choose easy or difficult routes that range from a few hours to all day. In late December, the weather is pleasant, sunny and 25 degrees Celsius. There are several stops along the way to hydrate and marvel at the scenery below — a magnificent Atlantic Ocean city with million-dollar waterfront homes at Camps Bay, and by contrast, slums along the outskirts. Rob doesn’t talk much about politics on the way up. He’s more interested in hearing stories from travellers who come to Cape Town to experience its white sandy beaches, five-star food at the V&A Waterfront, and unparalleled wineries. Stellenbosch, a couple hours drive from Cape Town, is a must for any wine enthusiast, although the Big Bus tour stops at several picturesque wineries within the city limits. The rewards of making it to the top of Table Mountain far outweigh the risks of getting bush rash or victimized by crime. Weather dependent, you may find yourself standing on Table Mountain’s famous tablecloth — a pillowy cloud of fog that hangs over its majestic cliffs. The way down is easy, if you choose. The cable car costs 190 South African rand ($12 USD) and within 15 minutes you’re back at the bottom. Hikers with energy to spare can walk back down while there’s still daylight. By sunset though, darkness falls fast. Rob’s strategies for staying safe aren’t meant to scare — quite the opposite. Every city in the world has problems, although Cape Town’s reputation as unsafe presents a challenge of its own. Travel anywhere requires vigilance. I never felt unsafe in Cape Town. Thanks to tour guides like Rob, visitors to Cape Town can experience a truly remarkable city and an unforgettable outdoor adventure to one of the natural wonders of the world.