In early September, I took my tween boys on a quick mother-sons trip to the Bay Area. Jason sat out this trip, as he was covering call for the weekend for general surgery. The last time we visited San Francisco was in 2019 ! I wasn’t sure what to expect, and imagined there had been many changes since the pandemic. I’m glad to report that we had a wonderful time and really enjoyed the city! In this post, I’ll share our 2-day itinerary that includes iconic landmarks, hidden gems, and even a redwood grove.
Getting There & Where We Stayed
Flight: We took a quick and easy flight on Southwest from Orange County to Oakland. Weekend warriors, we left after work and school on a Friday evening. I used a Companion Pass for one of the boy’s ticket, which made this trip more affordable!
Hotel: I booked the Hyatt Regency San Francisco (5 Embarcadero Center, San Francisco, CA 94111) using Chase points. The location was so convenient and a short walk from the ferry building and Salesforce Park. A friend gifted me a Guest of Honor pass, so we had access to the club lounge and free parking! After a 17 year hiatus, the 34th-floor club lounge started spinning again in 2024. We absolutely loved getting breakfast and snacks in the lounge, and soaking in the 360 degree panoramic view of the city skyline and Bay.
Saturday Itinerary
Stop 1: Golden Gate Bridge
Our first stop was the iconic Golden Gate Bridge. Before our trip, I learned that the Landon Court “Overlook” Lot offers one of the best parking options —and it’s free! From the lot, it’s just a short and scenic path to the bridge. We walked halfway across, soaking up the views, before turning back and heading to our next destination.
Tip: On weekends, don’t wait too long to arrive. When we pulled in around 11 a.m., the lot was already full, but we managed to snag a spot as someone left. By the time we returned around 12:30 p.m., there was a long line of cars waiting to park. GPS: Langdon Court, San Francisco
Stop 2: Pier 39, Fisherman’s Wharf, Ghiradelli Square
Next, we headed to the touristy heart of San Francisco, and honestly, the boys loved it. Pier 39 was buzzing with energy: street performers, souvenir shops, and the famous sea lions lounging by the docks. We grabbed some seafood and classic clam chowder in a sourdough bowl at Fog Harbor Fish House.
From there, we strolled along Fisherman’s Wharf over to Ghirardelli Square. I was pleasantly surprised to find the San Francisco Maritime National Historical Park Visitor Center, where we ducked in to learn a bit about the area before treating ourselves to decadent Ghirardelli ice cream sundaes. 🍦
Tip: If you’re short on time, Pier 39 and Ghirardelli Square are the highlights to prioritize. Many restaurants in the area validate 1-hour parking at the Pier 39 public lot (Fog Harbor did for us!), which saves some money.
Stop 3: Hotel Break + Salesforce Park
After a quick rest at the Hyatt, we walked over to Salesforce Park, a 5.4-acre rooftop garden above the Salesforce Transit Center. Opened in 2019, it’s a peaceful little oasis in the middle of downtown SF, with themed gardens, fountains, walking paths, beer garden and play area for kids. 425 Mission St, San Francisco, CA 94105
Tip: It’s free to visit! Take a slow stroll, enjoy the views, and soak in a little calm before heading to your next stop. You can either take an elevator or free tram up to the park!
Stop 4: Ferry Building + Hog Island Oyster Co.
Next up was the Ferry Building, which is full of amazing food stalls and unique shops—definitely worth exploring even if you don’t have a long list of must-haves. Since we love oysters, we made a stop at Hog Island Oyster Co. The line looked intimidating at first, but it actually moved pretty quickly; we only waited about 30 minutes on a Saturday night.
The oysters were incredibly fresh and delicious, and everything else we ordered was just as delightful. It’s a fun spot for families who enjoy good food and want a lively, local experience right on the waterfront.
Stop 5: Sunset Views at the Hyatt Club Lounge
We wrapped up the day back at the Hyatt Club Lounge, where we grabbed some dessert. We enjoyed the twinkling city lights and the soft glow on the Bay Bridge. It was a perfect to end a busy day exploring San Francisco.
Tip: Even if you’re not staying at the hotel, the Embarcadero area is a beautiful spot for sunset views.
Sunday Itinerary
Stop 1: Relaxing at the hotel and take out dim sum.
One of the reasons we came up to the Bay Area was for the boys to participate in a mini headshot session with Casa Studio. I’ve been a fan of photographer Priscilla Gragg for years and love how she captures children’s energy so authentically. Before heading to our shoot in Oakland, we had a relaxing morning. Taking advantage of the Hyatt’s excellent location, I walked just steps outside to pick up to-go dim sum from Harborview Seafood and coffee/hot chocolate from Philz Coffee.
Tip: Make a reservation if you plan to dine in, because the lines can get long. And the Mint Mojito Coffee at Philz is my favorite—definitely worth a try! ☕✨
Stop 2: Photoshoot
I recognize this is not a stop most families will make, but if for anyone who might be looking to get headshots for their kids with the dream team, Casa Studio offers these mini sessions once or twice a year. Follow their instagram for dates and details. Here are a couple of my favorites from the boys’ shoot. Email me if you want to book them 🙂 .
Stop 3: Post-Shoot Treat at Boba Guys – Rockridge
After the photoshoot, we couldn’t resist grabbing a treat at Boba Guys in Rockridge. Located at 5925 College Ave, Oakland, CA 94618, this spot is known for its high-quality bubble tea and cozy atmosphere.
Stop 4: Redwood Glen Trail at Redwood Regional Park
Next, we headed to Redwood Glen Trail in Redwood Regional Park, just a short drive from downtown Oakland at 7867 Redwood Rd, Oakland, CA 94619. This trail is a hidden gem—the towering redwoods and peaceful surroundings made it feel like a world away from the city. It was the perfect spot to unwind and enjoy a bit of nature with friends.
Tip: If you’re short on time and can’t make it to Muir Woods, this is a fantastic alternative for a quick, refreshing hike.
Final Thoughts
In just under 48 hours, we packed in so much — Golden Gate Bridge, Pier 39, Ghirardelli, Salesforce Park, the Ferry Building, a photoshoot in Oakland, and even a peaceful redwood hike. We had such a blast exploring San Francisco and the surrounding Bay Area. It was a perfect mix of city sights, tasty food, outdoor adventures, and quality time together. Even in a short weekend, you can create so many memories. This trip reminded me how special little adventures can be when you’re fully present with your kids.
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