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Urban Hikers: Free Your Mind With Some Fresh Air

View from Tank Hill
View from Tank Hill
Urban Hikers San Francisco

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Who: Urban Hikers
What: Urban hiking tours (stairways, hills, hiking trails of San Francisco)
Where: San Francisco |
Why: We like to say, "Whether
 you've been here 10 minutes, 10 days, or 10 years, you're guaranteed to see
 something new." Locals should pay attention to Urban Hiker because they can make you feel like you are on vacation, even in your own town. They show you all of the things you wouldn’t typically see or pay attention to and curate those sites into action-packed 2.5 – 3 hour hours.

How did you transition from Google (the tech world) to founding Urban Hike? Where did the concept come from? (Alexandra Kenin) When I left Google, I realized I had lived in San Francisco for 4.5 years, but that I didn’t really know the city that well. During that time, I had spent most days between 7 am and 7 pm at my job on the peninsula. I used to say to myself, “I wonder what San Francisco looks like in the daytime!” I loved Google (and I actually still do quite a bit of consulting work with them through an agency, Wordsmithie where I work about 15 hours a week), but I couldn’t take the commute anymore. I quit in January 2012.

When I left Google and was thinking about my next career move, I decided to take some time to visit all the places in San Francisco I had wanted to see, but had never had time to visit like the 16th Avenue Tiled Steps, Fort Funston, Stern Grove, and more. At the time, some of my other friends were between jobs and came along to explore the city with me. I discovered a number of hiking trails, hilltop views, and stairways that gave me a new appreciation for my city. I realized I wanted to share my findings with other people and thus was born Urban Hiker SF.

The only problem was that I wasn’t sure I really wanted to start a company. Honestly, I didn’t think I had an entrepreneurial bone in my body! I found, however, that the more I looked at job listings online, the more I couldn’t picture going back to my old office life. I decided to give Urban Hiker SF a try and we’re now celebrating our 2nd anniversary!

Tell me more about the hiking tours (the general areas/districts, why those areas?) (Alexandra Kenin) Here are general descriptions of our three hiking tours including the neighborhoods that they visit and their schedules. Our hikes are all 4.5 – 5.5 miles and take 2.5 – 3 hours. Our morning tours start at 9:30 am and end just in time for lunch. Our afternoon tours start at 1:30 pm and let hikers have lunch before joining us for a tour. They are all loops – meaning they start and end in the same location.

Urban Jungles

Castro/Upper Market/Twin Peaks (Wednesday at 9:30 am, Friday at 1:30 pm, Saturday at 9:30 am) Urban Jungles is our most popular hike. It's 3 hours/5 miles and has a good mix of urban and natural settings. This hike starts and ends at the Castro Theater (easy for public transportation, hard for parking) and goes through the Castro, Upper Market, and Twin Peaks neighborhoods. Some of the highlights include the Seward Street Steps, sweeping city views from hilltops, and a eucalyptus forest. The hike is moderately strenuous to strenuous.

I created this hike since one of the best hikes in the city is a hike up to Twin Peaks. The area also has a number of other great hilltops to explore. Lastly, The Castro is easily accessible by public transportation, so I thought hikers would be able to easily get to/from The Castro Theater, the start/end point of the hike.

Tales of the City

North Beach, Russian Hill, Telegraph Hill (Saturdays at 1:30 pm) Tales of the City is 2.5 hours and 4.5 miles. It's shorter than the other hikes, but it is probably the most strenuous since it has a lot of stairs and hills. This hike is on city streets for 99% of the tour. The hike starts and ends at Levi's Plaza, but we can shorten the hike to end at 2 hours at Washington Square Park. This tour takes place in the North Beach, Telegraph Hill, and Russian Hill neighborhoods. It has decent public transportation and parking options. Highlights of this tour include hidden alleyways and secret parks that not even the neighbors know.

I chose this area to be close to the visitor activity of Union Square. This tour lets people visit Coit Tower and Lombard Street (sights they'd want to see anyway) while seeing a number of hidden sights too. This area has a number of great attractions such as the parrots of Telegraph Hill, Jack Early Park, and the Filbert and Greenwich Street Steps.

Presidio Exploration

Pacific Heights/Presidio (Sundays at 1:30 pm) Presidio Exploration is 2.5 hours and 5.5 miles. It's our longest hike, but our easiest one. It has the most nature of any tour and explores the Bay Area Ridge Trail and Ecology Trail. You will also see 3 large scale Andy Goldsworthy artworks. This tour starts and ends right by the Lyon Street Steps in Pacific Heights, but spends 99% of its time in the Presidio. This tour has great parking (abundant 3 hour parking spots), but takes a little longer to get to on public transportation. At the end of the tour, I can leave you at the Inn at the Presidio for wine and cheese in front of their fire pit if you like. While this one is a little out of the way, it's great for hikers of all levels.

The Presidio is a natural choice for hikers as the neighborhood features 25 miles of hiking trails! It's also interesting from a historic perspective having been a Spanish, Mexican, and US military post. Lastly, there are three Andy Goldsworthy artworks here that let you combine art with your history.

How do you find your locations? (Alexandra Kenin) As a Xoogler (ex-Googler), I definitely rely on Google Maps to do an initial mapping out of my routes. Then, I do the hikes on foot and make adjustments based on things I discover on the ground. Each hike has between 40-50 turns, so it takes a lot of work to learn the routes!

How should people prepare for the tours? What can expect during the tour? (Alexandra Kenin) Anyone who can walk 5 miles is prepared for our tours. :) We also stop 10 times during each tour to cover history of the sights we are seeing. Before our clients take a hike with us, we send them out a prep email telling them what to wear, what to bring, etc. Basically, if you wear sneakers and bring sunscreen and water, you'll be fine!

What happens if someone can’t finish the tour? (Alexandra Kenin) Luckily, this has only happened on private tours, and has only come up once or twice in two years of business. If we had someone who absolutely couldn't finish a tour, we'd make sure they could get transportation back to the start point. We'd also be happy to issue them a full refund.

We provide hiking tours and emphasize that we are never in a race! We go at a sustainable pace for the group, which helps everyone keep up. If we have a larger group, we bring along a second guide to watch over the back of the pack.

Are the tours kid and/or pet-friendly? (Alexandra Kenin) Our tours are suitable for most people over 12 years old, but may be too strenuous for younger children. We've taken 10 and 11 year olds on our tours, but parents can decide how fit their children are on a case-by-case basis.

As for pets, I LOVE dogs, so as far as I'm concerned, dogs are always welcome. Not everyone loves our four-legged friends, so here is my general rule:

  • If someone with a dog is the first person to book a tour and they want to bring their dog, then that tour automatically becomes a dog-friendly tour.
  • If someone is not the first to book and wants to bring their dog, I'll first make sure this is ok with all he other hikers before turning the hike into a dog-friendly tour.

Are reservations required? (Alexandra Kenin) Yes - we require reservations and customers can book on our website, Schools, community groups, and corporations can book a private tour by emailing us at

Do you have any plans to franchise Urban Hiker? (Alexandra Kenin) I don't have plans to franchise at the moment because we still have lots of growing to do right here in San Francisco. We have high double digit growth and want to focus on maintaining or increasing our tour quality while increasing our volume. Franchises could definitely be a possibility for the future though - I can definitely envision an Urban Hiker LA, Seattle, or Portland.

What's next for Urban Hiker? (Alexandra Kenin) Right now, my big project is to write a book documenting all the hiking trails in San Francisco. I was inspired by Adah Bakalinsky's Stairway Walks in San Francisco and want to create my own book. I'll be submitting my book proposal to a first round of publishers on Monday of next week.

Check out the slide show to see images of some of their tours.

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