Today we’d like to introduce you to Alexandra Kenin.
Hi Alexandra, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
When I moved to San Francisco in 2007, my father gave me a copy of Stairway Walks in San Francisco by Adah Bakalinsky. For years, I intended to use the book, but it just gathered dust on my shelf. At the time, I was working at Google in Mountain View. Because of the long commute, I spent four and a half years leaving early and coming home in the dark, rarely getting the chance to truly explore the city I lived in.
That changed in January 2012 when I decided to leave my corporate role. Finally ready to dive into that stairway book, I took some time off to explore San Francisco on foot, venturing out to the 16th Avenue Tiled Steps, Fort Funston, and Sutro Forest. I was amazed by how much the city had to offer.
Then, the inspiration hit: what if I could combine my love of walking and hiking with urban sightseeing? After researching running tour businesses and meeting with local operators, I officially founded Urban Hiker SF. We launched later in 2012 and are still going strong today! We offer a variety of routes exploring the stairways, hills, and historic trails of San Francisco for small groups, private parties, and corporate team-building events (you can learn more at www.urbanhikersf.com).
My deep dive into the city’s terrain eventually helped me secure a publishing deal with Mountaineers Books. I have since written three books for their Urban Trails series: Urban Trails: San Francisco (2016), East Bay (2020), and Peninsula & South Bay (February 2026). I’m proud to say I’ve sold over 30,000 copies of my first two books, with a few thousand more of the latest edition already out in the world.
In the past few years, I tackled another massive passion project: mapping San Francisco’s public stairways. There are over 1,000 of them, so it was a huge undertaking! I created a public map (https://bit.ly/sfstairmap) and a companion spreadsheet (https://bit.ly/sfstairsheet) to share the data. The response has been incredible—the San Francisco Chronicle even featured the project, and the map has been accessed over 250,000 times by locals and visitors alike.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
My business has not always run smoothly! I’ve never actually run it as my full-time business since I have been a bit trepidacious to take the full plunge into entrepreneurship. I do believe there is potential there, but San Francisco is an expensive city to live in. It’s been great to have a part-time job at a creative agency to have a more regular income, but I know my own business could grow more if I could nurture it with my full attention.
Here are some stumbling blocks I’ve encountered over time.
1. Guides & Scaling: Training an urban hiking guide can be intensive. It requires mastering a route with some 40 turns, local history, and group management. Because it’s a specialized, part-time role, finding the right fit—someone with a flexible schedule who is willing to put in the upfront practice—can be tough. Right now, I’m running our weekday corporate tours myself to ensure that high standard, but I’m actively looking to build back our weekend team with passionate local explorers.
2. Pandemic. During the pandemic, the travel industry was at a low point, and San Francisco was, too. While in the past, San Francisco had been a gorgeous city to visit through and through, it was a bit depressing to navigate through the city in 2020 and 2021. Visitors weren’t coming, corporate groups weren’t coming, and the city felt empty. Thankfully things have changed, and San Francisco has visitors and conference attendees again, so I have noticed an uptick in groups booking.
We’ve been impressed with Urban Hiker SF, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
Urban Hiker SF is the premier (and only!) urban hiking operation in San Francisco. We specialize in small-group, private, and corporate team-building tours that explore the stairways, hills, and trails of the city.
We have a number of tours listed on our website (www.urbanhikersf.com), and we can also personalize our tours to meet any need – whether you want a quick ½ hour running tour or one-hour walking tour before your conference, a fun team building activity with a custom activity (like a redwood-themed bingo game we made for one of our clients), a one-way hike, and all-day hike, or something else.
What sets us apart is the sheer depth of our expertise. As the founder, I’ve literally written the books on the subject—specifically, three bestselling guidebooks for Mountaineers Books’ Urban Trails series covering San Francisco, the East Bay, and the Peninsula & South Bay.
Furthermore, as mentioned above, I’ve mapped over 1,000 of San Francisco’s public stairways into a community Google Map (https://bit.ly/sfstairmap) that has been viewed over 250,000 times.
We are proud to be a woman-owned business that doesn’t just show people the sights, but actively connects them to the neighborhoods, history, and magic of San Francisco.
How can people work with you, collaborate with you or support you?
There are so many ways you can support me or collaborate with me. Thank you for asking!
1. Tours! Come to SF and join us for a tour! You can visit our website at www.urbanhikersf.com, but please just email me at info@urbanhikersf.com to schedule as we’re in the process of hiring some new guides right now, so our exact schedule is in flux.
2. Books! Our books make great gifts!
They are available on bookshop.org:
San Francisco: https://bookshop.org/a/80384/9781680510201
East Bay: https://bookshop.org/a/80384/9781680512564
Peninsula & South Bay: (https://bookshop.org/a/80384/9781680517309
They are also available on amazon.com (https://amzn.to/4vdRAGP) as well as in local bookstores.
3. Follow me on social media! You can follow me on Instagram (www.instagram.com/urbanhikersf) and/or Facebook (www.facebook.com/urbanhikersf). We feature videos of our favorite spots in SF.
4. Send random support! If you like what I do, you can buy me a virtual matcha!
https://buymeacoffee.com/urbanhikersf
5. Open to all sorts of collabs! I’d love to work on more UGC and brand deals this year, so brands can reach out with their ideas! I can wear your backpacks, socks, or shoes while I hike, test your products, or travel to your destination to show off the urban hiking opportunities there. I love traveling and have been to 48 states and 54 countries.I’ll go anywhere!
Contact Info:
- Website: www.urbanhikersf.com
- Instagram: www.instagram.com/urbanhikersf
- Facebook: www.facebook.com/urbanhikersf
- Linkedin: https://www.linkedin.com/in/alexandra-kenin-2118342/
- Youtube: https://www.youtube.com/@urbanhikersanfrancisco
