Exploring San Francisco with Teenagers

Since our boys were little, most of our vacations have involved camping or trips with extended family. Last summer, we rented a lakehouse for the first time with just our boys, then 13 and 16. For our oldest, that five-day vacation was four days too long. Lake life was too sleepy and we decided our family needed something more stimulating.

This year, we booked a trip to one of our favorite cities, San Francisco, and I got all four airline tickets with credit card points. I’ll get to that…

My husband and I lived in San Francisco in 2003, moving there shortly after we’d started dating. We boarded the plane to S.F. with a one-week dog sitting job, two duffel bags, and nothing else. Looking back, this is hilarious because neither one of us owned a dog or knew anything about how to care for one. But everything worked out and we quickly fell in love with the creativity and beauty of this city. After a year, we were called back to Portland for a job offer and our family, but I almost had to drag my husband out of there. He would have stayed forever.

Returning to San Francisco with our teenage boys opened up a whole new world we didn’t know existed while living there in our early twenties. This trip was perfect for teenagers and equally enjoyable for us. It’s tough to find one place that will appeal to four humans with different needs, but San Francisco did it.

We followed a list of suggested activities from my friend Lori, who had recently visited with her family, and of course, I did research on hikes. I’ll share what we discovered, but first, these tips:

Tip #1: Start EVERY day with Philz Coffee. This was the BEST cup of coffee I’ve ever had in my life, and coming from a gal who loves her coffee, that’s saying a lot. This pour-over cup of absolute heaven was the start to every morning of our trip.

Tip #2: Definitely try a self-driving car called a Waymo. It’s not as scary as it sounds…after the first ride anyway. We grew to love the smooth ride, relaxing music, and the way each drive began with a friendly bot’s voice, gently saying, “Welcome back, Jill.” We loved it so much that our question of the week became, “walk or Waymo?” We mostly walked (72 miles in 6 days, according to my husband’s watch), because it’s free and we’re an active crew that’s happier when we get our exercise. But for long distances, we Waymo’d, which didn’t seem any more expensive than Uber and you can’t tip an invisible driver.

Tip #3: Do not try to squeeze five people into a four person Waymo. The driver’s seat is off limits to passengers and squeezing four in the back will not do; that Waymo will pull right over and ask one person to exit the vehicle. Trust me on this one.

Here are the highlights from our trip, starting with three stunning hikes we did.

Batteries to Bluffs Trail: Head to the Presideo, San Francisco’s national park site, for a 2.3-mile loop along the western cliffs, featuring historic gun batteries, wildlife and stunning views of the Golden Gate Bridge. Instead of looping, we had our Waymo drop us off near Battery Boutelle on the northern end of this hike and followed the western side of the loop one way.

From the old battery, the trail is easy to locate on the left as it winds down wooden stairs towards the water. When you see a sign for the beach detour, do take it! This will lead you down to Marshall Beach and if you follow it to the end, you’ll be standing directly underneath the Golden Gate Bridge. It’s quite an experience!

Return in the way you came and the trail continues along the coast, winding through wildflowers with staircases and dirt paths. The southern end of this loop will take you to Baker Beach. This is where we continued south, instead of following the loop back to the start.

Redwood Grove Loop at Henry Cowell State Park: We borrowed Melzy’s car and drove to Santa Cruz (about 1.5 hours from S.F.) to see the Redwoods and explore a coastal trail. She suggested this as an alternative to the crowds at Muir Woods, where you can find redwoods just outside of San Francisco.

Although we did a shorter loop at Henry Cowell, you could spend a day here hiking. The redwoods are breathtaking and and you’ll feel like an ant in a giant land.

Shark Fin Cove: On our way to Henry Cowell, we drove the Pacific Coast Highway and stopped for a stunning coastal hike with dramatic ocean cliffs, secluded beaches, and a cove featuring a giant boulder shaped like a shark fin. As you descend the path to the cove, there is a cave tucked into the cliffs on the right. Our kids loved exploring this dark tunnel…never found the end, but they we were excited about it. The name of this hike on All Trails is Bonny Doon Beach and Shark Fin Cove.

‘Bring Your Own Big Wheel’ race: This race of mayhem down the crookedest street in San Francisco involves grown adults in costume, barreling down Vermont Street, the actual crookedest street in the city (nope, it’s not Lombard) on kids’ big wheels.

This annual affair, a beloved Easter tradition that has been running for 23 years now, was timed perfectly with our trip. My college roomate Melzy, who is a local, tried to find us last minute big wheels with no real luck. So we watched…and the pure joy on the participant’s faces and they raced down the steep, winding street with reckless abandon was truly contagious. My favorite was the golden bunny. It was Easter Sunday afterall.

San Francisco Magic Theatre at Marrakech: Jay Alexander’s mind blowing magic show at a historic speakeasy was definitely a highlight of our trip. Located on the outskirts of The Tenderloin District (a tough neighborhood) I’d suggest taking a Lyft or Waymo here vs. walking. That said, we felt perfectly safe being dropped off near the front door.

The show was held in a cozy, basement theatre with Moroccan flair. A space purchased by Robin Williams and gifted to Jay, in support of his craft. Jay’s history includes touring with The Rolling Stones, who hired him to entertain their guests. He’s that good.

Buena Vista Park: These secluded trails wind through oak woodlands in the city’s oldest park. Enjoy some incredible city views from its upper slopes. It’s a nice dose of nature in the middle of the city.

Golden Gate Park & The Conservatory of Flowers: This greenhouse and indoor botanical garden with its exotic plant collection infused us with a solid dose of oxygen and moisture-rich air after a long Maine winter.

Coit Tower: on Telegraph Hill for more views of the city. Tip, climb the Filbert Street Steps to Coit Tower. Considered one of San Francisco’s hidden wild spots, these 385 wooden steps climb through lush greenery and gardens. You’ll feel like you’re in a tiny jungle. On the return trip, take the Greenwich Steps, which run parallel to the Filbert Steps, but aren’t quite as steep.

Sea Lions at Pier 39: Our boys loved the sea lions. You could really watch them for hours, so entertaining.

Alcatraz: We took the ferry over with Alcatraz City Cruises for a tour of the old penitentiary. Eerie and fascinating.

Musee Mecanique: One of the world’s largest privately owned collection of antique arcades, located at Pier 45 in Fisherman’s Warf. This was a huge hit with the boys.

One shouldn’t write a post about San Francisco without talking about all the delicious food, which is abundant in this city. Our favorite restaurants were Pakwan in the Mission (Pakistani Indian), Ramenwell in the Mission (uh, ramen), Heist near Union Square for the best gluten-free pancakes and breakfast burritos, and Gus’s Community Market for healthy groceries and prepared foods.

Lastly, I’ll explain how we got free plane tickets with credit card points, a hack I learned from a budget travel podcast. We signed up for a Chase Sapphire Preferred credit card (which has great signup offers) and put all of our bills on it for one whole year. We put everything on this card, including our groceries, which cost about a gazillian dollars because we have teenage boys. In the end, our points earned us four direct flights to the West Coast for free (or bills we were paying anyway). I’m sure many of you already know about this free way to fly, but if not, I’m happy to pass along a good travel hack.

I feel that we’ve only scratched the surface of the endless things to explore in San Francisco, but do reach out if you want more details on any activities in this post!