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Drink Your Way Through San Jose (and Los Gatos)

Paper Plane San Jose12San Jose is an hour or so south of San Francisco, and is a larger city in population, but most of its residents have preferred to come up to SF for their nightlife, cocktails, and culture. Though I'd been paying attention to the very few cocktail bars that would pop up on the radar here and there, and increasingly kept meeting excellent bartenders from the South Bay at events and competitions, I had never made it down to explore the bars until last week.  

It turns out there is some great stuff happening. In downtown San Jose itself, the bars are huge! I expected them to be small venues built to hold 40 people but they seem like they could each fit 100+. Additionally, all of them (55 South, Five Points, Paper Plane, Haberdasher) were built for big rushes- three of them had bars spanning the length of the room with at least three bartenders working (and this was on a quiet Tuesday). 

Tony, tiny Los Gatos on the other hand, had surprisingly small venues - both The Bywater and The Lexington House are teeny tiny restaurants with bar programs, but not so much room at the bar. 

The other two venues - Orchard Street Kitchen in Campbell and Jack Rose Libation House just outside Los Gatos, were each large funky spaces with casual, seated crowds and unusually great liquor selections.

Most of the drinks at these bars were of top quality, most of the bartenders working were very knowledgeable, and I'd go to most of these bars again in a heartbeat. 

Long story short, the South Bay has some great stuff going on. What follows are pictures I pulled off my Instagram page, which you should be following anyway. 


Orchard City Kitchen, Campbell

The cocktails on the menu (all Star Wars themed with great names and puns) had unique ingredients like squash and boba pearls. Both our drinks tasted pretty mild (though good) despite their wild and exciting descriptions, so they excite your mind but don't freak out your mouth.

Orchard city kitchen campbell
Orchard city kitchen campbell


The Lexington House, Los Gatos

A tiny little restaurant where the drinks have unique touches from liqueurs like Batavia Arrack, Chartreuse and a variety of fortified wines.  

The Lexington House Los Gatos


The Bywater, Los Gatos

New Orleans-themed small restaurant from David Kinch of Manresa with cocktails by consultants Tin Roof (Claire Sprouse and Chad Arnholdt). I had their clarified Ramos Gin Fizz and it was delightful. They had a Pimm's Cup on tap and were celebrating the tiniest little Mardi Gras when we visited.

The Bywater Los Gatos

Jack Rose Libation House, Monte Sereno

Super cool, all-wooden indoor-outdoor restaurant with beer garden attached to a set of cabins that are (or were? I'm not quite sure of the status) rented out for weddings and other sleepover events. Huge selection of whiskey, and though most of the cocktails were pretty expectable, the one I had had a peanut butter foam atop a strawberry-infused spirit. So it was meant to taste like a PB&J. And it was delicious. 

Jack Rose Libation House Los Gatos


Five Points, San Jose

When we arrived a big brass band was setting up in the back section of this huge venue. But behind where that ends is another bar in the back room that has recently opened. (I don't recall if that was going to be a membership venue or limited capacity or exactly what, but it was going to be treated as a special place rather than just the back room.) I believe this bar is fairly new and they're still adapting it as they go along. 

Most of the cocktails seem to be made Jerry Thomas-era in format, but with a different selection of flavors (butter-washed tequila, apricot with port, passionfruit bitters) in the drinks. They also have a selection of house shots (like Sfumato and Smith & Cross) and a section of low-proof cocktails (most with fernet and amari). 

Five Points San Jose


55 South, San Jose

This corner clubby bar is the host to Tiki Tuesdays, which was happening when we visited. That seems to be one of their main events based on the listings on the website, though they also host many wine/beer/spirits tastings and 'tap takeovers' by breweries. It would be interesting to see how much it changes from night to night, as there was a lot of tiki decor. 

55 South San Jose1


Paper Plane, San Jose

I've met several of the crew from Paper Plane at events so I was looking forward to this bar, and it didn't disappoint. As mentioned I was expecting something small but nope! Huge. They have a graphic menu, punch on tap, cocktails from bars around the world, coconut orgeat, the whole shebang. 

Paper Plane San Jose1


Haberdasher, San Jose

Haberdasher is the bar at the site of the former Singlebarrel, which was one of the first (if not the first) bar trying to do the speakeasy vibe in San Jose. It's a very red room and coincidentally for our second round of drinks we all ordered red ones so they were like camouflage. Our first round of drinks were poured from the draft system - Gin and Tonic, Americano, and the two top-selling cocktails at most cocktail bars in America: The Old Fashioned and Moscow Mule.

Other drinks had ingredients like carbonated bourbon, matcha tea, oak syrup, and carrots (not in the same drink). If it wasn't our eighth bar of the night, I would have stayed for more. 

Haberdasher San Jose2
Haberdasher San Jose2