My Unplanned, Aimless & Delicious 3-Day San Francisco Itinerary

A few weeks ago, I took an entirely unplanned trip to San Francisco. The focal point of the trip was to check out my cousin’s first premiere film which played at the Roxie Theater. Beyond that, he and I mostly just ate, drank, and walked around SF until showtime.

And of course, I couldn’t not document all the delicious bites and fun things we got up to. 

So, without further ado, consider this my unofficial guide to how to spend three days in San Francisco! For more spontaneous travel guides, you can find those here.

Oh, and don’t forget to check out my reel on my trip to SF!

Day One: The MOMA, SF Ferry Building & Tons of Seafood

Where we ate: Taylor Street Coffee Shop, Hog Island Oysters, Sushi Shio

What we did: Visited the MOMA & San Francisco Ferry Building

For our first full day in San Francisco, we stuck close to the hotel for breakfast. Taylor Street Coffee had solid reviews and a pleasant, albeit cozy vibe. I’m a sucker for eggs benedict so I got the florentine. 

Service was good and the coffee flowed, which are my two biggest considerations in a good diner. At first, I thought it was on the pricey side, but by the end of the trip, I learned San Francisco ain’t no Kansas if you know what I mean. 

Less than 15 minutes from the diner was the San Francisco Museum of Modern Art. Tickets were $50/pp, but we spent an additional $5/pp to visit the video installation created by performance artist Ragnar Kjartansson. 

Honestly, I would have happily paid the $55 just to see his exhibit. It was genuinely one of the most moving, heartfelt musical/artistic experiences I’ve seen, featuring an hour-long performance across nine screens. 10/10 recommend!

After the museum, we walked to the historic San Francisco Ferry Building and indulged in some Hog Island Oysters as we took in the view of the SF-Oakland Bay Bridge. 

A tray of oysters on a bed of ice with a spoon, lemon wedges, and a serving dish of mignonette in the bed of ice.

For dinner, we went to Sushi Shio and shared the sashimi tray and sake flight. The sake flight featured four sakes, ranging from dry and floral to full-bodied, bready, and rich. The service was perfect, and we received a thorough explanation of each sake. 

The sashimi tray included toro – fatty tuna belly – which literally melted in your mouth with a savory, buttery smooth texture. It doesn’t take a lot to win me over with fresh seafood, but I can honestly say this was the best sushi I’ve ever had! No wasabi needed… okay, maybe a little.

Day Two: San Francisco Chinatown, Little Italy & Drinks at Vesuvio

Where we ate: Pinecrest Diner, Caffe Sport, drinks at historic Vesuvio Cafe

What we did: Walked through San Francisco Chinatown & Little Italy

The next day we again stayed pretty close to the hotel, stopping at the Pinecrest Diner. It was more of a traditional eggs-and-toast Americana diner that lacked any pretentiousness. The huevos rancheros were solid and the portions were generous. 

Later on in the day, we walked through San Francisco’s Chinatown, which was definitely one of the more bustling Chinatowns I’ve been to. The open-air markets were all open early and vibrant aromas of fresh dumplings, meats, and seafood pervaded the air. 

I can never resist being one of one hundred groping for the freshest produce, taking in the brightly-colored array of fresh fruits. The only thing that made our walk better was the seamless transition into Little Italy. 

After strolling through the cafes and pâtisseries, we settled on Caffe Sport for dinner. The menu consisted of authentic Sicilian cuisine served in a brightly-colored dining room decorated with woodcarvings. 

A serving of pasta carbonara garnished with black pepper and fresh herbs. In the background is a plate of oysters.

We chose to sit outside and I ordered an Aperol Spritz with the carbonara. My cousin ordered the linguini with clams and we split a half dozen oysters. Our server brought out fresh focaccia with a thickened tomato sauce for dipping. 

Portions were generous, and service was good. I enjoyed my carbonara, which was balanced with the perfect amount of pepper and a delightfully savory and thickened sauce. My cousin’s linguini was loaded with aromatic flavors of garlic alongside a very generous portion of mussels. 

Overall, it was authentic cuisine offered in an attractive – though a bit noisy – outdoor space. 

After dinner, we walked the short 5-minute walk to the Vesuvio Cafe, an SF iconic bar known for its beat-writing inhabitants like Jack Kerouac and Neal Cassady. We’d been to this bar once before, and I loved the eclectic Bay Area memorabilia and cozy, creative atmosphere. 

The Vesuvio Cafe sign.

Day Three: The Painted Ladies, Tanner’s Full House & a Show at the Roxie

Where we ate: West of Pecos, drinks at the Hilton rooftop bar, Cityscape

What we did: Visited the Painted Ladies, Tanner’s Full House, and a show at the Roxie Theater

For our final full day in SF, we had a quick breakfast at a diner I was less than impressed with, then we got our steps in. We walked the 1.5 miles to the Painted Ladies, a historic row of homes built in a Victorian style that have made their way into San Franciscos’s most well-known films. Afterward, we walked another 20 minutes to the Full House for a quick photo (mostly for the gram) before heading closer to the theater to grab a bite.

For dinner, we ate at West of Pecos, a southwestern-themed restaurant and bar with a thorough list of vegan and vegetarian options. We split the guac and I got the chicken fajitas, though it was a hard choice between that and the butternut squash enchiladas.

My cousin got the Modelo-battered fish tacos. The fish was perfectly crisp on the outside, tender and flaky on the inside, and complimented perfectly with a spicy creme sauce on top. We each got a Cadillac margarita, because why not?

After dinner, we headed to the Roxie, a San Francisco Mission District landmark, and the perfect way to end a very successful 3-day trip to San Francisco.

The Painted Ladies in San Francisco.
Photo courtesy of Jesus Garcia
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