Paul Kushner
Beneath the modern facade of San Jose lies a secret world of bygone glamour and clandestine indulgence. Step back in time with us as we uncover the city’s hidden treasures—the best speakeasies in San Jose. These covert establishments harken to the Prohibition era, offering an intoxicating blend of mystery, craft cocktails, and timeless charm. Join us for an intriguing journey through San Jose’s speakeasy scene, where whispered secrets and carefully crafted libations create an unforgettable night out.
Haberdasher
43 W San Salvador St, San Jose, CA 95113
Phone: (408) 792-7356
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Located in the same plaza as San Jose Theaters and Symphony San Jose, Haberdasher is one of the best speakeasies downtown to settle in for whiskey tasting and conversation after a show. The highlight of this intimate basement hotspot is the Bootlegger’s Whiskey Syndicate, an exclusive tasting program consisting of the owner’s curated stock of rare bottles. If you’re not feeling up for low wine, there are plenty of other options from their Craft on Draft menu, including one of the best Palomas I’ve ever had the pleasure of drinking.
55 – Fifty Five South
55 S 1st St, San Jose, CA 95113
Phone: (408) 288-6000
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I discovered 55 South after spending an afternoon at the San Pedro Square Market. In desperate need of something refreshing to beat the summer heat, I wandered southeast down 1st Street, where I came across this intimate cocktail lounge at the corner of Post. The drinks were off the charts, and I could taste the passion they put behind every pour. I paired my order of Cream Cheese Bread with a State of Grace, followed closely by a top-of-its-class Bramble.
Five Points
169 W Santa Clara St, San Jose, CA 95113
Phone: (408) 982-5816
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Named after the Five Points neighborhood in New York City, you can find this San Jose speakeasy less than a block east of the Santa Clara & Almaden Avenue bus stop. I love that it takes so much inspiration from 19th-century speakeasies, with its warm, intimate vibe and focus on old-school cocktails. I sampled the “From the House” menu and thoroughly enjoyed my picks of Nell’s Wedding, a jammy Jamaican rum treat, and the delightfully fruity Rose of the Wild Bunch.
Paper Plane
72 S 1st St, San Jose, CA 95113
Phone: (408) 713-2625
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There have been many date nights when my partner and I spent the afternoon at the San Jose Museum of Art and walked less than five minutes northeast for dinner at Paper Plane. On my most recent visit, I asked the server for cocktail and wine pairings for their homemade gnocchi with forest mushrooms. She nailed it with her recommendations of Domaine de Montreuil Calvados-based Long Patrol topped with a beautifully spiced chai whipped cream and the dry fruitiness of Erath Resplendent Pinot Noir.
3rd & Bourbon
93 E Santa Clara St, San Jose, CA 95113
Phone: (408) 320-2453
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As the name implies, 3rd & Bourbon specializes in American whiskey cocktails. You can find it at the corner of Santa Clara and 3rd Street, next to Mexico Bakery. While not located in a basement or behind a secret door, the distressed wood and exposed brick give this San Jose gem a distinctly cozy feel. I spent a couple of hours people-watching while enjoying their happy hour craft cocktails, including a scrumptious Blackberry Bourbon Mojito and a refreshingly fruity Kentucky Buck.
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