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Los Gatos Soda Works

12 Top-Notch Cocktail Bars Around the South Bay

The best bars from San Jose to Los Gatos

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Seeking the kind of cocktail bar that tastes and feels like an adventure? We love a homey hole in the wall as much as the next person, but sometimes you want a place with a little more oomph.

You’re in luck. The places on this list are dripping with personality. Among their number are a clandestine speakeasy and a tropical tiki bar, a retro gamer lounge and an industrial-themed joint. Of course, beyond décor, there are the drinks themselves. The mixologists of these destinations push the envelope in both presentation and flavor. They reach for oddly-shaped glasses and bestow their masterpieces with enticing names. If they can’t coax you beyond the Moscow mules and margaritas, no one can. Here are 12 top-notch cocktail bars in the South Bay.

Health experts consider dining out to be a high-risk activity for the unvaccinated; it may pose a risk for the vaccinated, especially in areas with substantial COVID transmission.

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Note: Restaurants on this map are listed geographically.

3rd & Bourbon

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Can’t get enough of the industrial-themed destinations? 3rd and Bourbon – a small, but intimate space – should go on your list. With its modern American fare, the bar’s menu aims to please a variety of visitors. So lean on the classic burgers and beers combo or go bold with the Cajun chicken pasta and a grapefruit and thyme martini. As the name suggests, this bar’s bourbon menu is also impressive.

MINIBOSS

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Looking for ways to revive your inner kid? We suggest the retro glory of MiniBoss and its slew of vintage arcade games. Opt for the pinball machines (Deadpool, Star Wars, and Stranger Things among their many themes) or beeline it for the old-school joystick games with their nostalgically pixelated graphics. Between bouts of Miss Pac-Man and Donkey Kong, make sure to glance up and appreciate the bar’s glowing tetris wall and gamer murals. Fully embrace the playfulness of this place by ordering the Ziggy Piggy, a zany beverage served in a pig mug with a tiny pink balloon. Note: If MiniBoss tickles your fancy, also be sure to check out LVL UP in Campbell.

Dr. Funk

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Festooned with palm fronds and puffer fish, tikis and traveler’s chests, Dr. Funk will have you imagining yourself seaside within seconds. Add to this drinks like the Siren’s Song and Fog Cutter, and you half expect a pirate to swagger into the room. Curious about the name? The bar’s patron saint was a brazen 1800s physician who practiced medicine and mixology in the South Pacific, married the daughter of a pirate, and befriended the author of Treasure Island. Fun fact: If San Jose’s newest tiki bar reminds you of the iconic Smuggler’s Cove of San Francisco, that’s because it shares the same designer.

Dr. Funk

Five Points

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For a criminally good time, skulk on over to downtown San Jose’s Five Points, a pub with a Gangs of New York slant. Its namesake (Five Points, New York) was a lawless neighborhood back in the 19th century, and the cocktail list features drinks named after the area’s six gangs and includes vintage photographs of some of the more notorious members (including a gentleman with a top hat and a meat cleaver). And who wouldn’t feel like a badass ordering Tax and Death Evasion or Blood, Lust, & Diamonds on the rocks? The ambiance would make Scorsese proud with murky lighting, a penny floor, bookshelves lined with novels and busts, exposed beams, and a library ladder beside the shelves of alcohol. Insider tip: Visit Monday for live jazz.

Five Points

The Fountainhead

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The Fountainhead, an urban haunt in downtown San Jose’s art district, is named after a classic novel about a young architect, and the cocktail menu compliments the architecture magazines on the tables. Take, for example, the Greene and Greene — a blend of Japanese whisky, ginger liqueur, lime, green tea, and mint, which recognizes an architecture firm known for its extravagant bungalows — or the Aalto — a drink featuring rum, horchata liqueur, lime, cinnamon, and nutmeg named after one of the modernist masters. The Fountainhead is housed within the Sofa Market food hall, so after you stop by the bar, circle around to the other vendors for tacos, sushi, or poke.

The Fountainhead

Haberdasher

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Housed in a 100-year-old building, this basement-turned-bar offers a window into a previous era. To fully embrace the environment’s old-timey nostalgia, order a Belafonte, named after the Jamaican-American songwriter. Apparently, if this singer’s soul were distilled down to a flavor, he’d be a blend of Elijah Craig barrel proof, pineapple rum, cocchi americano, amaretto, and lime bitters. With drink in hand, settle into one of the red curtained booths and savor some sax-heavy Motown music. Make sure to appreciate the bowler hat light sconces, which tie in with the establishment’s 1920’s tailor shop theme — as do the measuring tapes the bartenders wear around their necks.

Katie Bloom's

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For those seeking the coziness of an industrial-themed lounge, Katie Blooms is the place. Brimming with Edison bulbs and brickwork, this recently renovated Irish pub makes a snuggly getaway. Katie Blooms’ is located in Campbell’s charming downtown—so after your Irish car bombs and Guinness, go ahead and take a lap around the block.  Consider yourself warned: It can get a little loud on weekends, but if you’re hoping to hold a conversation, you can always retreat to the bar’s spacious patio.

The Vesper

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For a taste of whimsy, find your way to The Vesper. Here, you’ll discover a lackadaisical chandelier with teeny lampshades over each bulb hanging from the ceiling and a hodgepodge of upholstered furniture. You’ll also see funky art with large canvases and bold colors adorning the walls as well as a mannequin reclining on the upstairs balcony. The sweet and creamy Ainsley Fix is a fan favorite; the cocktail combines bourbon with citrus, pineapple, and Peychaud’s, adds a spritz of rose water, and tops it off with a fluffy egg white foam. The froth is crowned with a sprinkling of dried rose petals.

Shepherd & Sims

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If you skip straight to the cocktail menu at Shepherd and Sims, you’re missing out on part of the magic. Take time for a glance around at the wood slat ceiling, vintage mirrors, wicker patio furniture, and misty forest mural stretching the length of one wall. As for dishes, consider trying the poached Spanish octopus drizzled in smoked paprika oil or the duck confit tartine with meat, arugula and white cheddar loaded onto a toasted croquette. Diners also praise the house-made potato chips served with French onion dip and caviar. But on to the drinks. The house cocktails — like Shepherd’s Pie and Waste of Thyme — showcase a medley of flavors. But we’d like to give a special shoutout to Winters in Italy, a satisfying blend of rye, Montenegro, Amaretto, lemon, and bitters.

The interior of Shepherd & Sims with a mosaic tile floor, wooden tables, and white walls. Pops of color include a turquoise half-wall and a vase of flowers on the hostess stand. Photos by Patricia Chang

The Palms

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The Palms is a not-so-hidden gem in the middle of downtown Los Gatos. To find it, simply walk along the boutique shops and restaurants of the main drag until you spy the stately 1891 Queen Anne Victorian with the sprawling yard and sizeable porch.  This location really shines on summer nights when tables of diners spill across the lawn for an al fresco evening under the twinkling lights. Since this is a Pacific Rim-inspired restaurant, try a tropical drink like the “Forget Mary Ann, Where’s Ginger,” a Bulleit bourbon, ginger, and citrus cocktail named after two stranded characters on the Gilligan’s Island show of the 60s.

The Palms

Sidecar Modern Tavern

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With drinks running the gamut from frou-frou to macho, there’s something for everyone at Sidecar Modern Tavern. Choose your adventure: go floral with Pretty in Pink, a rosy cocktail topped with a single violet, or embrace your tough as nails side with the John Wick, which comes with a bullet lodged in the side of the glass. The decorations seem to be in the same vein. Dark paint… accented with unicorn pillows and a unicorn head mounted on the wall.

Los Gatos Soda Works

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With a tree-shrouded courtyard overlooking the neighboring hillside, the atmosphere surrounding Los Gatos Soda Works is an amiable one. The drinks, however, have a roguish edge. Start with Honor Among Thieves, A Pirate’s Life for Me, Inside Job, or Grand Larceny, then make amends with a barrel-aged Law Abiding Citizen. Owner Jason Seele has gained Most Imaginative Bartender recognition from Bombay Sapphire, and he brings out the big guns on special occasions. If you’re lucky enough to make a reservation, your drink just might come in a bird-shaped glass (with dried lavender sprigs for tailfeathers) or in a teeny-tiny bathtub (with a quarter-sized rubber duck floating atop a “bath” of champagne and yuzu foam).

Los Gatos Soda Works

3rd & Bourbon

Can’t get enough of the industrial-themed destinations? 3rd and Bourbon – a small, but intimate space – should go on your list. With its modern American fare, the bar’s menu aims to please a variety of visitors. So lean on the classic burgers and beers combo or go bold with the Cajun chicken pasta and a grapefruit and thyme martini. As the name suggests, this bar’s bourbon menu is also impressive.

MINIBOSS

Looking for ways to revive your inner kid? We suggest the retro glory of MiniBoss and its slew of vintage arcade games. Opt for the pinball machines (Deadpool, Star Wars, and Stranger Things among their many themes) or beeline it for the old-school joystick games with their nostalgically pixelated graphics. Between bouts of Miss Pac-Man and Donkey Kong, make sure to glance up and appreciate the bar’s glowing tetris wall and gamer murals. Fully embrace the playfulness of this place by ordering the Ziggy Piggy, a zany beverage served in a pig mug with a tiny pink balloon. Note: If MiniBoss tickles your fancy, also be sure to check out LVL UP in Campbell.

Dr. Funk

Dr. Funk

Festooned with palm fronds and puffer fish, tikis and traveler’s chests, Dr. Funk will have you imagining yourself seaside within seconds. Add to this drinks like the Siren’s Song and Fog Cutter, and you half expect a pirate to swagger into the room. Curious about the name? The bar’s patron saint was a brazen 1800s physician who practiced medicine and mixology in the South Pacific, married the daughter of a pirate, and befriended the author of Treasure Island. Fun fact: If San Jose’s newest tiki bar reminds you of the iconic Smuggler’s Cove of San Francisco, that’s because it shares the same designer.

Dr. Funk

Five Points

Five Points

For a criminally good time, skulk on over to downtown San Jose’s Five Points, a pub with a Gangs of New York slant. Its namesake (Five Points, New York) was a lawless neighborhood back in the 19th century, and the cocktail list features drinks named after the area’s six gangs and includes vintage photographs of some of the more notorious members (including a gentleman with a top hat and a meat cleaver). And who wouldn’t feel like a badass ordering Tax and Death Evasion or Blood, Lust, & Diamonds on the rocks? The ambiance would make Scorsese proud with murky lighting, a penny floor, bookshelves lined with novels and busts, exposed beams, and a library ladder beside the shelves of alcohol. Insider tip: Visit Monday for live jazz.

Five Points

The Fountainhead

The Fountainhead

The Fountainhead, an urban haunt in downtown San Jose’s art district, is named after a classic novel about a young architect, and the cocktail menu compliments the architecture magazines on the tables. Take, for example, the Greene and Greene — a blend of Japanese whisky, ginger liqueur, lime, green tea, and mint, which recognizes an architecture firm known for its extravagant bungalows — or the Aalto — a drink featuring rum, horchata liqueur, lime, cinnamon, and nutmeg named after one of the modernist masters. The Fountainhead is housed within the Sofa Market food hall, so after you stop by the bar, circle around to the other vendors for tacos, sushi, or poke.

The Fountainhead

Haberdasher

Housed in a 100-year-old building, this basement-turned-bar offers a window into a previous era. To fully embrace the environment’s old-timey nostalgia, order a Belafonte, named after the Jamaican-American songwriter. Apparently, if this singer’s soul were distilled down to a flavor, he’d be a blend of Elijah Craig barrel proof, pineapple rum, cocchi americano, amaretto, and lime bitters. With drink in hand, settle into one of the red curtained booths and savor some sax-heavy Motown music. Make sure to appreciate the bowler hat light sconces, which tie in with the establishment’s 1920’s tailor shop theme — as do the measuring tapes the bartenders wear around their necks.

Katie Bloom's

For those seeking the coziness of an industrial-themed lounge, Katie Blooms is the place. Brimming with Edison bulbs and brickwork, this recently renovated Irish pub makes a snuggly getaway. Katie Blooms’ is located in Campbell’s charming downtown—so after your Irish car bombs and Guinness, go ahead and take a lap around the block.  Consider yourself warned: It can get a little loud on weekends, but if you’re hoping to hold a conversation, you can always retreat to the bar’s spacious patio.

The Vesper

For a taste of whimsy, find your way to The Vesper. Here, you’ll discover a lackadaisical chandelier with teeny lampshades over each bulb hanging from the ceiling and a hodgepodge of upholstered furniture. You’ll also see funky art with large canvases and bold colors adorning the walls as well as a mannequin reclining on the upstairs balcony. The sweet and creamy Ainsley Fix is a fan favorite; the cocktail combines bourbon with citrus, pineapple, and Peychaud’s, adds a spritz of rose water, and tops it off with a fluffy egg white foam. The froth is crowned with a sprinkling of dried rose petals.

Shepherd & Sims

The interior of Shepherd & Sims with a mosaic tile floor, wooden tables, and white walls. Pops of color include a turquoise half-wall and a vase of flowers on the hostess stand. Photos by Patricia Chang

If you skip straight to the cocktail menu at Shepherd and Sims, you’re missing out on part of the magic. Take time for a glance around at the wood slat ceiling, vintage mirrors, wicker patio furniture, and misty forest mural stretching the length of one wall. As for dishes, consider trying the poached Spanish octopus drizzled in smoked paprika oil or the duck confit tartine with meat, arugula and white cheddar loaded onto a toasted croquette. Diners also praise the house-made potato chips served with French onion dip and caviar. But on to the drinks. The house cocktails — like Shepherd’s Pie and Waste of Thyme — showcase a medley of flavors. But we’d like to give a special shoutout to Winters in Italy, a satisfying blend of rye, Montenegro, Amaretto, lemon, and bitters.

The interior of Shepherd & Sims with a mosaic tile floor, wooden tables, and white walls. Pops of color include a turquoise half-wall and a vase of flowers on the hostess stand. Photos by Patricia Chang

The Palms

The Palms

The Palms is a not-so-hidden gem in the middle of downtown Los Gatos. To find it, simply walk along the boutique shops and restaurants of the main drag until you spy the stately 1891 Queen Anne Victorian with the sprawling yard and sizeable porch.  This location really shines on summer nights when tables of diners spill across the lawn for an al fresco evening under the twinkling lights. Since this is a Pacific Rim-inspired restaurant, try a tropical drink like the “Forget Mary Ann, Where’s Ginger,” a Bulleit bourbon, ginger, and citrus cocktail named after two stranded characters on the Gilligan’s Island show of the 60s.

The Palms

Sidecar Modern Tavern

With drinks running the gamut from frou-frou to macho, there’s something for everyone at Sidecar Modern Tavern. Choose your adventure: go floral with Pretty in Pink, a rosy cocktail topped with a single violet, or embrace your tough as nails side with the John Wick, which comes with a bullet lodged in the side of the glass. The decorations seem to be in the same vein. Dark paint… accented with unicorn pillows and a unicorn head mounted on the wall.

Los Gatos Soda Works

Los Gatos Soda Works

With a tree-shrouded courtyard overlooking the neighboring hillside, the atmosphere surrounding Los Gatos Soda Works is an amiable one. The drinks, however, have a roguish edge. Start with Honor Among Thieves, A Pirate’s Life for Me, Inside Job, or Grand Larceny, then make amends with a barrel-aged Law Abiding Citizen. Owner Jason Seele has gained Most Imaginative Bartender recognition from Bombay Sapphire, and he brings out the big guns on special occasions. If you’re lucky enough to make a reservation, your drink just might come in a bird-shaped glass (with dried lavender sprigs for tailfeathers) or in a teeny-tiny bathtub (with a quarter-sized rubber duck floating atop a “bath” of champagne and yuzu foam).

Los Gatos Soda Works

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