193: Getting Paid to Show Off Your City: How to Start a Tour Guide Side Hustle

On any given weekend in San Francisco, out of earshot from the barking harbor seals at Pier 39 and the clang of the cable cars, a small group of urban hikers are exploring the city from a different vantage point. For three hours, they walk, climb, and even slide their way through historic neighborhoods and scenic outlooks. They’re led by Alexandra Kenin, or one of her carefully selected guides, and have paid $49 apiece for this unique travel experience. Alexandra runs UrbanHikerSF.com on the side from her day job as a content writer and editor. More than 1000 people take her urban hikes each year, and she now oversees a team of 4-5 guides that can lead the hikes in her place.