Let’s Get Classy

Paper Plane

This bustling bastion of late-night elixirs features some of the best bartenders in America. If you don’t take our word for it, The Tales of The Cocktail Foundation ranked a Paper Plane bartender top 10 in the nation while also declaring the establishment itself a top 10 “highest volume” bar in the U.S. western region. So remember, when you bask in the ambiance of this high energy, sleek & sexy, exposed brick loving, and exquisitely staffed of a building, you’re encountering the finest San Jose has to offer.

SP2 Communal Bar + Restaurant

Emitting quite the cosmopolitan charm, between their gloriously spacious outdoor patio and illustrious interior, Communal has given life to an upscale experience that’s tough to match. Typically a great choice for brunch as well, their locally-sourced dinner menu features American bistro cuisine tailored by executive chef Paul Nuno.

On another note, for those planning events, the indoor venue can handle private parties from 20 to 300 guests; the outdoor patio lounge comfortably fits 150 guests and yes, it’s possible to rent the entire venue. They’ve hosted a variety of special events, including everything from Product Launches, Premier Parties, Cocktail Receptions, Formal Affairs, Corporate Events, Keynotes, and even Weddings.

Five Points

The bar’s namesake, a 19th century New York neighborhood known as Five Points, generated a notorious reputation that will live in infamy; defined by vice, poverty, and political corruption, the community captured Americans’ imaginations for over 70 years. A single bright spot in the history of Five Points is its wide recognition as the original “melting pot” of our nation; a place where people from all over the world converged and shared cultures, creeds, and customs.

Similarly, Five Points, San Jose, is a place where people can meet and mingle, and new traditions mix with old. With that being said, take a seat, soak in the old-school New York Vibes, sip on a timeless libation, and enjoy your patronage at the swankiest bar in town.

The Hedley Club

Located within the Hotel De Anza, live performance enthusiasts will love to hear, The Hedley Club is celebrated for hosting local artists on most days of the week. Their smooth rhythms & vibes pair perfectly with both the room’s sumptuous decor and that glass of Napa Valley wine in your hands – which, by the way, currently looks like it could use a refill; funny how that works.

Haberdasher

Careful, while strolling about downtown, you might just walk past one of the best joints for a craft cocktail in San Jose without even realizing it. Keeping lowkey, Haberdasher is an underground bar that’s marked only by the silhouette of a bowler hat and tie outside. Very reminiscent of a speakeasy vibe, this institution of extraordinary beverage amalgam’s has also organized the Bootleggers Whiskey Syndicate – a social club with whom they share their stash of the most coveted bottles around.

Cielo

Perched atop the Hotel Valencia, Cielo gives guests the chance to revel in a golden state sunset as it dips below picturesque rolling hillsides to the west. Whilst twilight descends upon San Jose and the stars begin taking their places in the night sky, savor this front-row seat to the magnificent show that is another evening in the city just south of the bay.

Fairmont Hotel Lobby Lounge

The Fairmont Hotel exudes world-class decadence from top to bottom and their lobby lounge is no exception. Upon walking through the main entrance, one can’t help but feel entranced by the resplendent interior – complete with riveting features such as marble pillars, alluring carpet patterns, fancy furnishings, and a prodigious chandelier hanging across the room. On the other end of that beautiful chandelier beckons the Lobby Lounge bar, calling to you like a welcoming old friend you haven’t seen in a while and who also looks to have done quite well for himself.

Note: The Fairmont’s Lobby Lounge is currently under construction. Should the remodel be carried out in the same taste as the rest of this building, the new design should look exquisite!

V Bar

A dimly lit room with leather seating and a glowing red undertone, V Bar is the kind of upscale lounge a classy comic book supervillain takes his girlfriend on Valentine’s day – is it brash to assume she’s not his wife? Anyways, let’s talk about the layout; it’s fairly easy to get cozy with a loved one in the more secluded seating, then there’s the bar’s countertop for any evening’s socialites, and finally a more unique hallmark is their balcony that overlooks Santana Row – providing a birds-eye view to those ingratiating themselves in San Jose’s nightlife.

55 South

Representing what can become one of the more crowded locations on our list, 55 South is an upscale lounge that serves exceptional craft cocktails, meanwhile, not skipping a beat with the weekend partiers. The classy ambiance coupled with a killer DAILY Happy Hour from 4:00 pm to 6:00 pm also makes them a local favorite for drinks after work.

Trials Pub

Admittedly, Trial’s Pub doesn’t quite give off the same ritzy impression as some of the more sumptuous lounges in town. However, Trial’s does have something no other bar could pay any amount of money for and that’s history! The building itself, among other purposes, has functioned as a grocery store, brothel (quite the leap, we know), then in the early 20th century, a prison (of which, jail cells still exist in the basement), headquarters for the United Farm Workers during the 70s, and finally, in 1997, a British couple opened Trial’s Pub on these hallowed grounds.

There’s a subtle charm about the joint – the kind of place you end up at and fall in love with all the while. An unapologetic authenticity, the warmth of your best hometown watering hole, decor that harkens back to a bygone era, and a glass of something that speaks to the soul are just a few Trial’s notable attributes.