My San Francisco

Started when Jacqueline Boland was pregnant with her son as a way to see the city through the new (often smudged) lens of parenthood, San Francisco-based Red Tricycle is a free email newsletter with a simple mission: to help parents have more fun with their kids. Offering ideas for things to see, do, eat, and more, Jacqui and her business partner, Drea Lester, are Bay Area experts, sharing advice for locals and visitors alike. Now in six cities, Red Tricycle presents a small, well-edited list of events, services and products to its discerning subscribers. To learn more, visit

Where: Your Red Tricycle email newsletter has become wildly popular among parents. Explain the service, how you came up with the idea, and to what you attribute Red Tricycle’s success?
JB: I started Red Tricycle as a way to connect with other parents who were also trying new restaurants, keeping up with cultural happenings, and planning fun weekend adventures, all with a 20-pound stroller in tow.

DL: When I came on board, we had just our Seattle market and about 18,000 loyal and engaged readers. I knew one thing for certain, our content was good, and I mean really good, which left only one real challenge—how to get the word out. Luckily, moms love to share awesome finds, so once we stepped up the outreach with social media and partnering with other awesome local businesses, we were off to the races!

Where: What is the most valuable advice you can give to parents visiting the Bay Area and traveling with children?
JB: We like to break up our “Explore” articles into two-hour chunks, because that’s how long you have a kid’s attention before they need a nap, food, a potty break or all of the above. You can pack 1, 2 or 3 “Explores” into your day, as long as you take breaks in between.

DL: There is absolutely no reason NOT to travel with your kids. In fact, I can think of no better way to give a child perspective in the world. Pick your favorite neighborhoods and areas you would like to see and then choose one place that you feel would be most fun. Also, skip the obvious touristy stuff and dig deep for the real gems that will end up being most memorable.

Where: Which SF neighborhoods do you find to be especially accommodating to families?
JB: I love a combination of urban buzz with open space, so my favorite neighborhoods are Presidio Heights (shop Sacramento Street’s great kids boutiques, then take a hike through the Presidio), Cole Valley (grab a chocolate malt at The Ice Cream Bar, then enjoy Golden Gate Park) and Cow Hollow (decorate a cupcake at American Cupcake on Union Street, then head down to Crissy Field to play).

DL: I would say Hayes Valley, Noe Valley, The Marina and The Inner Sunset (Irving Street).

Where: What are some of the best spots to dine out with the kids? Teens?
JB: I find that kids of all ages love the sights, sounds and flavors of Chinatown. Go for dim sum and let the kids pick their own dumplings and pork buns. They’ll squeal with delight at the strange-looking entrées (pickled chicken feet, anyone?). It’s a memory they’ll talk about long after the trip is over.

DL: Even after 18 years here, I am a Chicago Pizza girl at heart, so when Patxi’s came to town, I was over the moon. Not only do they have the best pizza in SF, they are super accommodating for kids. American Grilled Cheese Kitchen in South Park for the best grilled cheese around and Yank Sing for weekend dim sum.

Where: What are some of your favorite children’s shops?
JB: For the most eclectic finds, I love heading to the Mission. Paxton Gate has some really cool interactive kids toys. Aldea Ninos has great décor and 826 Valencia is the only pirate supply store in the city—a sure-hit with the 6-and-under set.

DL: Small Frys in Noe, Sprout on Union and Mudpie on Fillmore are some of my favorite kids boutiques.

Where: What is a must-do and must-see for parents and kids in San Francisco and the Bay Area?
JB: Crissy Field—the beach in the summer, a hot chocolate at The Warming Hut when the fog rolls in. A trip to Sausalito to visit the Discovery Museum. Have lunch at Cavallo Point and grab a photo with the Golden Gate Bridge and San Francisco skyline in the background. And a Giants game, of course.

DL: The Exploratorium and Palace of Fine Arts is probably my No.-1 must-do for families. I absolutely love spending time there myself, so it’s a win-win for everyone. Dolores Park and its newly remodeled playground should also be on the list. Also, one of my favorite “local” hidden gems is riding the glass elevators at The Westin St. Francis hotel. Go there, try it, you will see what I mean.

Where: How do you like to spend a day in the city with your kids?
JB: We love to explore the ships at Aquatic Park, then grab an ice cream sundae at Ghirardelli Square Ice Cream & Chocolate Shop, or sample the yummy foods at the farmers market at the Ferry Building. In the summer, outdoor concerts like the Stern Grove Festival), are a uniquely San Francisco experience.

DL: We love spending weekends either in Golden Gate Park or on the Marina Green.