We Olive & Wine Bar

This spot operates as two businesses in one: you walk through shelves of $40 olive oils and aged balsamics before reaching the wine bar and patio that overlooks Prospect Street. That retail-first setup keeps it off most visitors' radar, making it easier to snag a sunset table on the patio without the wait times you'd face at straight wine bars down the block.

The patio is the move here — it faces west over the village rooftops, which means prime sunset viewing without the marine layer blocking it out. On weeknights, it skews local, with neighbors stopping in after work. Weekends draw more couples and small celebrations, but the retail buffer keeps the crowds manageable even during high season.

The menu leans into what they sell up front: olive oil flights, tapenade samplers, and flatbreads that showcase the products. The artichoke flatbread gets mentioned consistently, as does the charcuterie board. The hummus comes drizzled with their house olive oil, which actually makes a difference. Wine selection runs toward boutique California producers and smaller European vineyards — expect staff to pour tastes before you commit.

Parking is Prospect Street standard (difficult). The storefront entrance can be confusing if you're expecting a traditional wine bar — just walk through to the back. They also sell retail to-go, which makes this a functional stop if you need a host gift before heading to dinner elsewhere below the bluff.

One downside: hours aren't posted consistently, and they sometimes close earlier than expected on slower weeknights. Call ahead if you're planning around a specific time. The retail focus also means the food menu is limited compared to full restaurant programs nearby — think small plates and boards, not entrees.