Speakeasy in the South Bay worth going out for.

I follow speakeasy in the South Bay closely and keep the ones worth going to. Tell me what you like and I'll send the ones that fit you.

Top picks

Heritage Pub and Chop House

Heritage Pub and Chop House

Los Gatos

Irish pub & chophouse

Second Story

Second Story

Los Gatos

Supper club revival

Italian Cellar Speakeasy Bar

Italian Cellar Speakeasy Bar

Little Italy

1920s Italian speakeasy

Jazz Up Your Monday Night

Jazz Up Your Monday Night

Mon, Jun 29 · 9:00 PM

Five Points

Downtown Historic District • $$

Live jazz & craft cocktails

Alhambra Irish House Blues Jam

Alhambra Irish House Blues Jam

Wed, Jul 1 · 7:00 PM

Alhambra Irish House

Centennial • $$

Improvised blues jamming

Little Italy San Jose Trivia Night

Little Italy San Jose Trivia Night

Wed, Jul 1 · 7:00 PM

Italian Cellar Speakeasy Bar

Little Italy

Italian heritage trivia competition

Little Italy San Jose Trivia Night

Little Italy San Jose Trivia Night

Wed, Jul 1 · 7:00 PM

Italian Cellar Speakeasy Bar

Little Italy

Italian and local trivia

St. James Gate

St. James Gate

Belmont • $$

Speakeasy meets island escape

Augustine

Augustine

West Valley

Coastal resort dining

Wursthall

Wursthall

Downtown • $$

German beer hall with california twists

Not everyone knows about these

Penelope Bourbon Tasting

Penelope Bourbon Tasting

Sat, Jun 27 · 5:00 PM

Unwind Bottle Shop

Mountain View

Bourbon in a mini-mart

Chicken Cock Whiskey Tasting

Chicken Cock Whiskey Tasting

Sat, Jul 18 · 4:00 PM

Unwind Bottle Shop

Mountain View

Rare whiskey hideout

WhistlePig Whiskey Tasting

WhistlePig Whiskey Tasting

Thu, Sep 17 · 5:00 PM

Unwind Bottle Shop

Mountain View

Unexpected whiskey hideout

Wunderbar

Wunderbar

Downtown

Intimate basement speakeasy

Secret Wine Bar

Secret Wine Bar

Downtown

Curated wines & views

Shyr Wines

Shyr Wines

Saratoga

Hidden wine tasting room

Browse by bars

Speakeasy in other cities

Frequently asked questions

How does Outgoing pick speakeasy in the South Bay?

I go through what's actually on locally and keep the ones worth going to. Nothing pay-to-play, no filler, just the things I'd text a friend about.

Are these picks up to date?

Yes. Past events drop off on their own and the list refreshes every day, so what you see is what's actually happening.

Can Outgoing recommend things for me personally?

That's the whole point. Tell me what you're into once, and I'll send you things that fit, by email and chat.

Do I need to download an app?

No. I live in your messages and inbox. Start from here, and we can keep the conversation going from your phone.

Does Outgoing cost anything?

No, it's free.

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