The second night in San Francisco ended up at Osso Steakhouse for both happy hour and dinner, which honestly turned out to be a pretty solid move.
And yes, before anybody asks, the happy hour cheesesteak absolutely distracted me immediately.
But we will get there.
Finding the Place
One thing to know about Osso Steakhouse is that it is a little hidden if you are not paying attention.
I literally watched people walk past it confused trying to figure out where the entrance was. It is inside the Presidential building near the Performing Arts Center, and because of the scaffolding outside, you actually cut through the parking lot to get in.
Once inside though, it completely changes.
Classic steakhouse vibe, dark woods, comfortable atmosphere, relaxed energy. Super chill overall.
The staff was friendly and attentive without hovering over you every three minutes asking if you are still working on that.
Sometimes less is more.
Happy Hour Was the Real Surprise
The happy hour menu was not gigantic, but honestly I would rather have a smaller menu done properly than fifty mediocre options nobody remembers.
And the pricing was actually pretty reasonable for San Francisco.
The standout immediately was the Philly cheesesteak with fries.
For around $25, it was a pretty big sandwich and honestly hit the spot perfectly after walking around the city all day. Gooey cheese, tender steak, solid bread, crispy fries. I personally would have liked more mushrooms, but that is just me trying to force vegetables into a cheesesteak conversation.
Still definitely worth ordering.
The Rest of the Meal
We also got the crab cake sliders, steak frites, and a ribeye au poivre.
The crab cake sliders were actually really good. Nice little pepper kick to them that gave the flavor some personality instead of just tasting like generic seafood filler. Definitely something I would order again.
The steak frites might honestly be one of the better deals on the menu. Around the mid-$20 range and surprisingly solid for the price point. Crispy fries, properly cooked steak, and enough food where you do not leave angry.
The ribeye au poivre was good, but not something I would personally reorder.
Nothing bad about it at all. Good steak, good peppercorn sauce, cooked properly. It just did not have that I need to come back tomorrow energy. Sometimes a dish is simply good and that is okay.
I would probably use the next visit to explore more of the menu instead.
Dessert and Final Thoughts
We wrapped things up with cheesecake, which was solid and did exactly what cheesecake is supposed to do after a steak dinner: quietly finish the mission.
Overall, Osso was definitely worth visiting, especially for happy hour.
Would I put it at the very top of my San Francisco steakhouse list? Probably not.
Would I absolutely go back for happy hour, steak frites, cheesesteaks, and another round at the bar? Absolutely.
And honestly, in a city where some cocktails cost the same as small utility bills, finding a steakhouse happy hour that actually feels worth it is a win.
Still plotting your San Francisco food crawl? Check out my House of Prime Rib review for giant martinis, spinning salad bowls, and enough prime rib to question your decision-making skills.
Next stop was Mustard Grill for the best American of the entire trip.
As always, what do I know? I am just a fat guy from Brooklyn trying to survive the week, one martini at a time.
Looking for more NYC restaurant reviews? Check out my Best Steakhouses in NYC, Best Burgers in NYC, and Best Restaurants in NYC lists.