Biking the Bay & Unexpected Moments: A Solo Two Days in San Francisco

Sometimes the best travel memories are the ones you don’t plan—and that was exactly the vibe of my solo two-day trip in San Francisco. I had extended a quick business trip to give myself a little breathing room and time to explore, and I’m so glad I did. What followed was a trip full of iconic views, serendipitous moments, and really good food.

Bay Views & a Surprise Proposal

I started my day riding a bike along the bay toward the Golden Gate Bridge, soaking in that crisp, salty breeze and the sound of the city just behind me. I eventually pulled over, grabbed an iced latte at the Warming Hut Park Store and took a quiet moment on a bench to admire the view—camera packed away, just enjoying the peace.

Then, out of nowhere, a guy approached me and asked if I could take a few photos of him and his partner. I said sure, and as I got ready with his phone, he said, “Just keep taking photos.” Slightly confused, I kept clicking—and seconds later, he dropped to one knee.

Full photographer mode activated.

Little did they know, they had asked a wedding photographer to capture their proposal. I documented the whole thing, gave them a few posing tips, and handed back a phone full of images they’ll probably cherish forever. Total magic.

Whiskey, Art & Bayfront Wandering

After that adrenaline spike, I wandered over to the Palace of Fine Arts, one of my favorite places in the city. It’s a photographer’s dream—grand architecture, reflecting pools, and endless texture and light. From there, I made a little detour to The Buena Vista, the bar famous for introducing Irish coffee to the U.S., and enjoyed a mid-morning pour with zero regrets.

For lunch, I stopped at the Ferry Building Marketplace for a bite and some casual people-watching, with Alcatraz just visible off the shoreline. I spent the afternoon exploring art galleries near Fisherman’s Wharf, where the mix of tourist buzz and creative energy felt electric.

Ending on a High Note

Before calling it a day, I stopped by San Francisco Brewing Co. for a flight of craft beer, and then treated myself to dinner at The Brazen Head—a cozy, old-school hideaway tucked into the Marina District. The prime rib and rye old fashioned was the kind of meal that makes a solo dinner feel like a celebration.

And before catching my morning flight home, I made one last stop at Saint Frank Coffee for a kouign amann and a vanilla latte—the perfect sweet ending to a trip I hadn’t planned but will never forget.

Final Thoughts: The Joy of Saying Yes to a Detour

This trip was short, spontaneous, and exactly what I needed. It reminded me that sometimes the best travel moments happen when you’re on your own, with no timeline, just a camera, a bike, and a willingness to say yes to wherever the day takes you.