Kenneth Lippman taking in the rays near Pioneer Park in Mission Hills (Courtesy photo)
Tour Operator Kenneth Lippman Takes Us to ‘Another Side of San Diego’
By Frank Sabatini Jr.
As owner and founder of San Diego’s most comprehensive tour company, Kenneth Lippman knows our city probably better than many natives and longtime residents.
Lippman moved here in 1999 and launched Another Side of San Diego Tours in 2007. He has since absorbed San Diego’s history, neighborhoods, landmarks, restaurants, and public art, as well as many scenic high points found in the far reaches of San Diego County.
His year-round tour company is based in The Gaslamp Quarter. It has attracted the attention of local and national media because of its large selection of tours, which cover a wide range of territory using various means of transportation.
Lippman gave us amusing insights into his operation and the types of people who make for good and bad customers while also bluntly sharing his views on city politics and our changing landscape.
Downtown Condo Guys: What originally brought you to San Diego?
Lippman: I’m from Cleveland and moved here in 1999. I had fallen in love with San Diego on a spring break before graduating from Ohio State University with a degree in journalism. I remember standing at La Jolla Cove and realizing that I didn’t know this kind of beauty existed in America. So I decided I’d move to San Diego after finishing my last college exam. I literally packed the car the next day and started driving west.
Downtown Condo Guys: What kind of work did you find here before starting the tour company?
Lippman: I worked for JP Morgan Chase but got laid off because of the mortgage crisis of 2007-2008.
Downtown Condo Guys: How many different types of tours do you offer? And which are the most requested?
Lippman: A lot—about 100 different tours that include city tours, walking and Segway tours, private tours and more. They are all held within San Diego County except for a San Diego-L.A. tour that we offer.
My two most popular tours are done in Mercedes vans. They are the San Diego Tour, which covers Balboa Park, The Gaslamp, the Embarcadero, and Coronado. The other is a tour that covers La Jolla. Each of them takes about three hours.
Downtown Condo Guys: On average, how many tours per week do you conduct?
Lippman: It can range from 20 tours a week to more than a hundred. My business is seasonal and we have about a dozen tour guides who work part time. We are the busiest during summer, holidays and spring break.
Downtown Condo Guys: Do you get many sign-ups from local residents?
Lippman: Yes. About half of my business comes from locals looking to do something fun. And because of the economy, we’re back in staycation mode.
Downtown Condo Guys: What were some of the urban sights you highlighted when first starting the tour company in 2007?
Lippman: The foot of Fifth Avenue where the historic Gaslamp sign is. The San Diego Convention Center. Seaport Village. The lily pond and botanical building in Balboa Park. The Maritime Museum of San Diego, and the Unconditional Surrender Sculpture. They are all still on our list today.
Downtown Condo Guys: What attractions have you added since then?
Lippman: Petco Park; the USS Midway Museum; and more recently the new restaurants at the foot of Broadway and the Piazza Basilone in Little Italy. Also some urban art such as the Pacific Soul Sculpture by artist Jaume Plensa on the corner of Pacific Highway and Broadway.
Downtown Condo Guys: In keeping with your company’s name, what are some of the places or areas that fall into that ‘other side’ of San Diego?
Lippman: We cover everything from the heehaw areas of Julian and Cuyamaca State Park to the Bohemian vibes of Ocean Beach and the surf culture of Sunset Cliffs—plus everything in between. It was my original idea to take people to places in San Diego that wouldn’t automatically be on their bucket lists—to off-the-beaten path places.
For some of the city tours we go into actual neighborhoods and look at places people can easily miss, such as Pioneer Park in Mission Hills or the nearby Meshuggah Shack, which is a tiny little coffee shop. In Little Italy we’ll include the Crack Shack, where people love to take pictures of the giant chicken out front. Or on the Embarcadero, where people usually don’t know about the Bob Hope Memorial, which sits between the USS Midway and The Fish Market restaurant. Some of the other neighborhoods and their surrounding areas that we cover include the East Village, Barrio Logan, Hillcrest and Old Town.
Downtown Condo Guys: Do any of your tours stop at restaurants for actual meals?
Lippman: Yes. We have historical walking tours that include restaurants throughout the city, such as Meze and Chocolate SD both in the Gaslamp, and Filippi’s in Little Italy. We also do a beer tour called the North Park Brewery Tour. Outside of those, I keep paper lists of all my favorite restaurants for clients to take.
Downtown Condo Guys: Are there any particular landmarks or areas in San Diego that draw surprise reactions from your tour customers?
Lippman: Balboa Park always has that awe effect on people. Many don’t realize that our city park is bigger than Central Park in New York.
Downtown Condo Guys: What are some of the logistical failures that might occur during a tour?
Lippman: Tires can go flat and bikes can break down. Or if there’s a marathon, it’s hard to get around the city, and it could be difficult getting to the starting point of a tour. Weather can also sometimes affect a tour. But that is rare because of our beautiful climate.
Downtown Condo Guys: Who are your ideal tour participants? And who is the most difficult?
Lippman: My favorite participants are those coming with an open mind, ready to experience the wonders of San Diego. The most difficult types—well there are Karens everywhere. We sometimes deal with people who have expectations that can’t be met. It isn’t just one particular group, but there are also those who try to take over a tour with their own narratives.
Downtown Condo Guys: How has urban San Diego changed for the better and/or worse since you started the company 18 years ago?
Lippman: What I love are all the new hotels and businesses that have opened up. There is also money that has been put into the Embarcadero and now there are plans to redo Seaport Village.
But we need to immediately fix the homeless crisis downtown and put parking rates back to what they were. I can’t believe how many mayors and bad politicians over the years said they will find solutions to the homeless problem. If I could put my foot up someone’s ass, I would. As a person who loves San Diego, it’s a shame.
Downtown Condo Guys: If I were giving a middle-age friend or relative who lives in the burbs one of your tours as a Christmas gift, which one would you recommend? And which tour would you suggest for someone in their 20s or 30s?
Lippman: For the middle-age person, definitely our Plunge E-Bike Tour, which covers Mt. Soledad, Birdrock, La Jolla Village, and La Jolla Cove. For 20 and 30-somethings, maybe our Gaslamp Segway tour because it basically turns downtown into a Disneyland Ride. It’s like they’re surfing the concrete.
Downtown Condo Guys: When you travel to other cities, do you take guided tours or do you prefer exploring on your own?
Lippman: I love taking guided tours—not only to see how the other tour companies operate, but to also hear about the back stories of how places became what they are today.
